The Kosher Capones: A History of Chicago's Jewish Gangsters 9781501747335

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THE KOSHER CAPONES

THE

KOSHER CAPONES

A History of Chicago’s Jewish Gangsters BY JOE K R AU S

NORTHERN ILLINOIS UNIVERSITY PRESS AN IMPRINT OF CORNELL UNIVERSITY PRESS ITHACA AND LONDON

Copyright © 2019 by Cornell University Press All rights reserved. Except for brief quotations in a review, this book, or parts thereof, must not be reproduced in any form without permission in writing from the publisher. For information, address Cornell University Press, Sage House, 512 East State Street, Ithaca, New York 14850. Visit our website at cornellpress.cornell.edu. First published 2019 by Cornell University Press Printed in the United States of America ISBN 978-1-5017-4731-1 (cloth : alk. paper) ISBN 978-1-5017-4733-5 (pdf) ISBN 978-1-5017-4732-8 (epub/mobi) Book design by Yuni Dorr Librarians: A CIP record is available with the Library of Congress. Cover image courtesy of Sun-Times Media.

CONTENTS

vii

A C K N O W L E D G M E N T S 

I N T R O D U C T I O N 1 2 3

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C O NNEC TIN G T H E D O T S   3

TH E END, O R ZU K IE’S B AD D AY  13

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B EY O ND S C ARFAC E, A K O S H ER C APO NE F O R M A X W E LL S T R E E T   23

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TH E S U NS ET O F 1974: L ENNY PAT RIC K ’S C H A N G I N G W O R LD   37 4 5 6

L ANDING IN L AW NDAL E  49

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R IS ING IN T H E R ANK S   67

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R O O T S O F T H E L AW NDAL E M ACH I N E   77

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ARVEY ’S B AL ANC ING AC T   89

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S Y NDIC AT E H AM M ER   113

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9

S IZING U P TH E O U TF IT  123

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1 0 1 1

W H EN S C AR FAC E M ET RICO   145

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1 2

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L ENNY ’S C IR C U S T U RN  157

A F T E R W O R D

C A S T

T ENTAC L ES   135

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O F

N O T E

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A Q U ES TIO N AN S W E R E D   169

C H A R A C T E R S  

O N

S O U R C E S  

N O T E S 

185

B I B L I O G R A P H Y  I N D E X 

217

173

181

213

ACKNOWLEDGMENTS

You don’t spend thirty years digging on a project without getting a lot of help. Starting with the finish, I am deeply grateful to Amy Farranto for taking a shot at this, and I thank the copy editors and anonymous referees from Northern Illinois University Press, whose insights helped me hammer this into final shape. I am grateful as well for the years of support I’ve received from the University of Scranton, where a recent sabbatical has put me over the finish line. An earlier research grant permitted me to purchase a copy of Lenny Patrick’s testimony in the Gus Alex trial, and the University library has been generous in its help with interlibrary loans and photographic digitization; thanks there in particular to Kristen Yarmey, Betsey Moylan, and Kevin Kocur. I also want to acknowledge a grant from the University’s Weinberg Jewish Studies program that has helped make it possible to license many of these photos from Sun-Times Media. In my early years of researching this material, I was fortunate to find myself part of a group of supportive and knowledgeable friends. Walter Roth and I shared the same goal, and I benefited from his energy and his introductions through the Chicago Jewish Historical Society. Norman Schwartz generously looked up distant leads for me, and Dan Sharon of the Spertus Institute’s Asher Library sent me every puzzle piece of the history that came his way. John Binder has been as generous with me as he has with everyone doing research on Chicago’s Prohibition gangsters, and through him I came to know Rich Lindberg, Larry Raeder, and several others in and around the Merry Gangsters Literary Society. In our “Jewish wing,” Nate Kaplan was generous in sharing the oral histories he took as part of preserving the cultural memories of Davey Miller. And Bill Reilly, alongside his wife Helen, was an all-around friend and inspiration, one of the first who made me believe I could write this book. I’ve benefited over the years from conversation and correspondence with others curious about the history of Chicago’s Jewish gangsters from general or familial curiosity, including Abe Marovitz, Sylvia Friedman, Mike Karsen, Craig Eisen, Wayne Johnson, Jerry Levine, and David Abrahams, who graciously permitted me to use photos of his relative Manny Abrahams. I could not have wrapped this up as I did—nor could I have seen the connections between Lenny Patrick and the trials that cripple the Outfit—without generous time and energy from Chris Gair. I’ve

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Acknowledgments

also been fortunate to have a lot of research help over the years, especially from Blanche Keno, Tom Baldwin, and Josh Kraus. And then there were those who, in their professional capacity, went above and beyond to make things easier for me, including Jeremy Martin at Doc’s Sports, Toby Roberts at Sun-Times Media, and Jeanette Callaway and Elisabeth Saffell at the Chicago Crime Commission. Finally, I have to thank family and friends for putting up with me throughout this seemingly endless process. My long-suffering roommates Alex Bogdanovitch, Bill Huston, and Ray Marx took phone messages from all sorts of strange callers. Bill Irwin has listened to complaints and offered advice on many a morning run. Annie Nichols has always been there as a reader and a support. My cousins Steve Miller, Rob Miller, Leah Miller, Eric Miller, and David Miller—from my father’s side of the family and so, the name being merely coincidental, not related to the Miller brothers—have all helped with access to Chicago-only research materials and general encouragement. My in-laws, Roz and Gene Chaiken, have always looked for ways to help. And my brother Ed and sister-in-law Amy have cheered at every seeming step forward, sympathized over each setback, and done everything they could think to help me tell this story of ours. Above all, I thank my wife Paula Chaiken for putting up with me when I drifted into the tangents of this history, for her patience when I closed the study door, and for her enduring love and support when I resurfaced into our law-abiding life together. I thank my sons as well—Richie, Max, and Teddy—who’ve had to endure all sorts of gangster stories at all sorts of unlikely moments. And last, I thank my parents: my father who’d have burst with pride over seeing a finished copy of this, and my mother who started it all with her question.

THE KOSHER CAPONES

Introduction CONNECTING THE DOTS

I Sometime in the middle 1980s my mother asked if I would look into a rumor she’d heard: her father, Max Miller, was a gangster who, along with his brothers Davey, Hirschie, and Harry, were caught up in Al Capone’s Prohibition wars. Her father died in 1928 when she was only two, so she had no firsthand memories, but she wanted to know something about his world. Was it true, as reported by The Joker Is Wild, the 1955 best-selling biography of comedian Joe E. Lewis, that he’d been killed by gang boss Dean O’Banion?1 And what, she wanted to know, had happened to her family when the Jewish gangster world started to fade at the end of Prohibition? Over the next several years I scoured old newspapers, found my way into largely forgotten files, and talked with old-timers. I got to know the popular and academic studies on organized crime, and while several had good information on Chicago as a whole or Jews of other cities, it quickly became clear that no one had ever focused on the intersection of Chicago and Jewish gangsters. Histories of Jewish Chicago, for instance, didn’t seem to have a place for the Jewish gangster. The first definitive such work, H. L. Meites’s History of the Jews of Chicago from 1924, seemed consciously to ignore the major criminals of the period,2 focusing instead on commercial and cultural leaders. The second, Irving Cutler’s The Jews of Chicago, which came out in 1996 after I’d had the opportunity for much of my own research, presented a substantially broader cross-section of the city’s Jewish experience. Even it dedicated only a single paragraph to the gangsters, although I was glad to see it note that “the

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Davy Miller boys” played a crucial role in battling the “gentile youth gangs that harassed the yeshivah students or taunted the elderly long-bearded Jews.”3 From the other direction historians of Jewish organized crime seemed to have little to say about Chicago. Alan Block in East Side–West Side: Organizing Crime in New York, 1930–1950, did an admirable job of cutting through what amounted to Hollywood legend and the sort of history I would come to recognize as the “Scarface” style, but he focused only on New York and the political-economic nature of criminal organization. Jenna Weisman Joselit made her Our Gang: Jewish Crime and the New York Jewish Community, 1900–1940 a model for demonstrating how legitimate Jewish communal organizations framed their responses to the notoriety of Jewish gangsters, but while her study had implications for the Jewish community across the country, it too had little to say about Chicago. And Albert Fried, whose The Rise and Fall of the Jewish Gangster in America remains the fullest attempt at telling a national story of the Jewish gangster, essentially threw his hands up about Chicago. While Fried focused on New York, he offered surveys of other cities including Minneapolis, Kansas City, Philadelphia, and Boston. When he turned briefly to Chicago, though, he noted that my grandfather and his associates in the early Prohibition era were “man for man as ferocious as any in the country,” yet he had no explanation for why their gang had such a different experience than the Jewish gangs of other cities. As he put it, “Why it failed whereas far lesser Jewish gangs made good elsewhere in America is an intriguing question, but it is not one that can be dealt with here, if it can be dealt with at all.”4 That felt like a challenge, and I set about answering not just my mother’s original question but the larger one about the world in which her family was only one chapter. In the vacuum that seemed to exist around it, I became an authority on the West Side Jewish figures, not just my grandfather and his brothers but also Nails Morton, Julius “Lovin’ Putty” Anixter, Morris Eller, and Jules Portugese, who sometimes allied and sometimes fought, but who always seemed to get defined in relation to the larger world of Italian and Irish organized crime. I tracked down nearly a dozen episodes that had exploded onto newspaper front pages—ranging from the time my great-uncle Hirschie killed two off-duty policemen in 1920 to Davey Miller’s getting replaced as referee in the historic 1927 Jack Dempsey–Gene Tunney “Long Count” boxing match—collecting everything I could about each distinct character and controversy. Over time I began to appreciate some of the forces driving those stories: the demographic fact that Jews were moving from Maxwell Street to the farther West Side; the economic fact that the most lucrative crimes shifted

Connecting the Dots

5

from gambling and booze to gambling and racketeering; and the political fact that city power grew ever more centralized as the famous Democratic machine developed. I discovered eventually that my grandfather’s West Side world slowly coalesced from a series of gangs competing with each other into a final independent Jewish organization headed by Benjamin “Zukie the Bookie” Zuckerman. That early, wide-open gang warfare gave way gradually to a model of confederation, where gangs across the city and within the Jewish underworld agreed to respect the territorial lines as Johnny Torrio, boss of what would become the Capone gang, drew them.5 Davey Miller and the rest of my family were originally a part of that plan and then, as the markets tightened, Zuckerman and his partners squeezed them out. Zuckerman, who’d been Anixter’s protégé, rose as much through his role in the hardscrabble machine politics of Lawndale as through his capacity for violence. He supported the politicians who could grant him protection from law enforcement, and in turn, he accepted the “concession” for running crime in the area. Once Prohibition ended, when gambling returned as the lifeblood of crime, Zuckerman stood at the top of the Jewish underworld, overseeing his operations from the same restaurant Miller had opened soon after World War I. For a long time I thought of that as where the story ended. I published a handful of articles and gave regular talks to community groups, but as a researcher, I’d hit a wall. I’d had ambitions of putting my findings into some larger form, of writing a book that would answer the original questions I’d pursued, but the story didn’t quite feel large enough. I had pieces, but I couldn’t make them come together as a larger narrative. Then in 1992 Lenny Patrick became a household name, at least for a few months. Patrick, a seventy-eight-year-old gangster, described in many places as the head of the Jewish wing of the Syndicate, agreed to testify in a pair of explosive trials against Gus Alex and Sam Carlisi, two of the Syndicate’s bosses. In a city notorious for Italian American gangsters like Tony Accardo, Sam Giancana, and Tony Spilotro, Patrick stood out as an anomaly. He was a Jew who’d remained important in organized crime long after the crumbling of the West Side Jewish world I’d studied, someone rumored even to have had a hand in the Kennedy assassination. Unlike my grandfather and other gangsters of his era who had a veneer of nostalgia that seemed to soften their crimes, he’d been threatening and hurting people through the 1980s. The old-timers who liked to reminisce about Prohibition-era figures didn’t think it was quite as much fun kibitzing about Patrick. No one seemed to want to share the details of his rise

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nor to explain how he came to have the reputation for particular nastiness. No one, as far as I could tell, had ever attempted a full history of him. Patrick generated a lot of interest in the early 1990s. He was in the papers and on the news, and his testimony against Alex and later against mob boss Sam Carlisi looked to make a real dent in the leadership of the Outfit. People began asking me how he was connected to Jewish organized crime of the Prohibition era, and, while I didn’t have a good answer, the question implied there had to be one. He’d come from that same world, but he represented a different experience, rising not as a figure in the independent Jewish gangster operation that Zuckerman controlled but as a Jewish figure in the Syndicate that grew out of the Capone gang. He’d somehow emerged from the wreckage of that West Side Jewish gangster world to hold down a cabinet-level position in corporate organized crime. In his testimony against Gus Alex, he recalled stories from his adolescence in Lawndale and then moved on to the shady parts of North Side Chicago where the old-time Jewish tough guys relocated as the greater Lawndale area lost its Jewish character. In other words, he stood for the sequel to the story I already knew. He and the Syndicate he represented had taken over from the gangsters who’d won the Prohibition wars. I still needed to find how those two halves of the story fused together, though. Like almost everyone in Chicago, I had a sense of the history of the Syndicate. I knew it through the “Scarface” version in which a crazed Al Capone shot his way to dominance over the city, and thanks to a wave of researchers like Laurence Bergreen, Robert Schoenberg, Gus Russo, and Nick Tosches, I came to know it as a more complicated history of criminal confederation. Hollywood may have liked to make it seem that a single gangster would rise up and call the shots for a generation, but the real history ultimately had more to do with the way criminals developed new strategies for organizing themselves. Lenny Patrick’s rise came at the expense of Benny Zuckerman, but it also represented an ever more tightly organized Syndicate triumphing over an earlier model that afforded separate gangs a measure of independence. This book, then, is my attempt at connecting the dots of the seemingly separate stories of the Jewish gangsters in Chicago. It’s a single story with distinct chapters, one that begins with the roots of the Jewish Prohibition gangsters at the turn of the last century and ends with the unraveling of the Syndicate in the early 1990s. Most of the first half of the narrative deals with the independent organization Zuckerman consolidated during World War II, while the second half runs from Lenny Patrick as a young man in the Syndicate to Lenny Patrick as an old man

Connecting the Dots

7

in the Syndicate. Along the way, it takes in a history of the corrupt Jewish politicians who enabled the independents as well as the corporate gangsters who overwhelmed them. Taken as a whole, it spans the twentieth century, reflecting the changing nature of Chicago’s organized crime as well as the changing experiences of Chicago’s Jewish community.

II Once I had a sense of the range of that story, once I could point to the succession of gangsters who stood at the heart of Chicago Jewish organized crime, I found myself asking a fresh question: why had no one told the complete story before? It seemed clear to me there was a straightforward sequence of characters and events. Jewish politicians like Manny Abrahams, Morris Eller, Michael and Moe Rosenberg, Jacob Arvey, and Arthur Elrod followed one another as the brokers of protection from law enforcement in Jewish Chicago. Independent gangsters like Jules Portugese, Davey Miller, Julius Anixter, and Benny Zuckerman flourished through Prohibition into the rise of the Syndicate as they controlled crime in the densely Jewish neighborhoods of Maxwell Street and greater Lawndale. And finally, Syndicate gangsters like Lenny Patrick, Jack Guzik, David Yaras, and Frank “Lefty” Rosenthal took over after they killed Zuckerman and as the Jewish community gradually relocated from the West Side. It was, I thought, a mostly straight line. As I came to see eventually, though, that line, even if it was unbroken, twisted in two key directions. The first such “twist” came in the transformation of citywide gangster organization. From at least 1871, when the Great Chicago Fire redrew the city’s map, there had been complex criminal networking, first through the machinations of gambling boss Mike McDonald6 and then through the corrupt First Ward Democratic organization headed by Mike “Hinky Dink” Kenna and “Bathhouse” John Coughlin.7 With the coming of Prohibition, however, suddenly very wealthy gangsters began coordinating with one another more directly. They asserted their equal standing with the politicians and established a confederation—the Syndicate as Johnny Torrio mapped it out—designed to prevent upstarts and limit competition among themselves.8 The Miller brothers, for instance, flourished in those early Prohibition years, depending on support from the gangsters behind Republican Mayor “Big Bill” Thompson. Benny Zuckerman’s later rise came largely because he was more effective at allying with the gangsters

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backing the subsequent Democratic machine of Anton Cermak and Jacob Arvey, but the point was the same. Independent Jewish gangsters succeeded when they could find a foothold in that larger network. What began as a gangster alliance, however, developed into a criminal monopoly. The Torrio Gang, which would soon become the Capone Syndicate and eventually the full-blown Outfit, started as the first among equals but gradually absorbed or overwhelmed its rivals. In the decades after the St. Valentine’s Day Massacre, Capone’s old Syndicate developed the power to swallow the remaining independents like Zuckerman. As it played out, the more centralized those political and criminal structures became, the more they subordinated Chicago Jewish organized crime. The gangsters of the Jewish neighborhoods, of Maxwell Street, Lawndale, and eventually the Far North Side, rose and fell in response to those citywide changes. They may have controlled crime locally, but they were themselves controlled by the larger forces organizing across the city. There is no central Jewish “godfather” of Chicago, no analogue to Capone, Lucky Luciano, Arnold Rothstein, Dutch Schultz, or Meyer Lansky. Instead, it’s a story of a succession of gangsters who, fighting selfishly for their own interests, represented larger demographic and political changes in the city. They were part of that story, but because they were rarely directing it, they were rarely its authors. The second substantial “twist” in the line connecting the dots of Chicago Jewish gangster history is that the Jewish community itself continually relocated. The Jews of turn-of-the-century Maxwell Street were typically immigrant and poor, living in aging and cramped apartments, and most of them moved out as soon as they had the opportunity. By the 1920s the majority of Chicago Jews had moved further west to the greater Lawndale area. There, in what historian Irving Cutler called “Chicago Jerusalem,”9 they established the most concentrated Jewish community in the city’s history, developing substantial wealth and witnessing the rise of an American-born and educated generation. They enjoyed comparatively larger homes and had access to Douglas and Garfield Parks, but the rise of the suburbs and the increased opportunity to live where they chose eventually inspired most of them to relocate. By the late 1950s the center of the community had shifted again, this time dispersing across the city and suburbs with concentrations, among other places, along the lakefront and in Rogers Park, Albany Park, Hyde Park, and Skokie.10 That migration had implications for the nature of Jewish organized crime. Scholars have long emphasized the link between the gang and the neighborhood. As far back as the 1920s, the sociologists of the University of Chicago produced a

Connecting the Dots

9

series of field studies and governmental reports theorizing how particular communities bred gang behavior.11 In the 1950s Daniel Bell proposed recognizing a “distinct ethnic sequence” as one group after another—the Irish, the Jews, and then the Italians—came to dominate organized crime as their neighborhoods in the major northern cities grew in influence.12 And in 1992 James O’Kane observed that many of the neighborhoods notorious for producing Syndicate-level gangsters, for instance Brooklyn’s Bedford-Stuyvesant, were losing a multigenerational ethnic character that seemed a necessary component of that process. Where once such stability had allowed gang bosses to establish what O’Kane called a “Pax Caponeana”—a play on the idea that Capone or Lucky Luciano, through their syndicates, had established a forced peace like the Pax Romana of Rome—new Latino and African American ethnic gangs flouted the old criminal structures.13 That is, without a stable, ethnic community, even the most expansive gangs would transform or unravel. In the case of Chicago’s Jewish community, never as substantial as New York Jewry nor as long-settled as Chicago’s Italian community, the center of gravity never remained in one place long enough to establish a multigenerational organization. Jewish organized crime persisted, and it was carried on in a clear succession, but it never had the attachment to a geographically defined space in the way of classic ethnic organized crime. Because Chicago Jews migrated in dramatic fashion within the city, they were less tied to the neighborhoods that bred traditional organized crime. To take the most significant example, the greater Lawndale community went from having little to no Jewish presence before World War I to what Cutler estimates was a population of 110,000 by the height of the Depression,14 to a small and aging population by the middle 1960s. In other words, it rose and fell as a Jewish community in less than two generations. A single individual could have been part of all three eras—as, indeed, Lenny Patrick was—and would therefore have seemed part of different narratives around Jewish organized crime. As a result, the history of the Chicago Jewish gangster is less connected to place than most gangster histories. There was continuity, but it was a continuity twisted around those rapid demographic changes.

III To put it metaphorically, the story of the Italian American gangster in Chicago— the story of Al Capone and his successors—is shaped like Italian bread, narrow

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and straight with knife marks scarring the length of it. The story of the Jewish gangster is shaped more like challah, with different strands braiding together to create a softer whole. The Italian American–dominated Syndicate has a mostly uninterrupted narrative, running from Capone’s mentors “Big Jim” Colosimo and Johnny Torrio to his eventual successors, Paul Ricca, Tony Accardo, and, finally, among others, Sam Carlisi. In contrast, the story of the “Kosher Capones” is broken, spliced, and woven back together. It’s twisted by the shifting neighborhoods where Jews congregated, the changing structures of organized crime, and the growing effectiveness of federal, state, and local law enforcement. It’s also the story of a group of underdogs, of gangsters who were never entirely in control of their own story. It’s about a series of characters who needed perpetually to react to or ally with other elements of Chicago’s organized crime, who fought to control a piece of the action while others were ultimately controlling them. At bottom, three braids combine to form the history of the Chicago Jewish gangster. There’s the independent strand that runs from the early shtarkers, tough guys, of Maxwell Street, like Manny Abrahams, Jules Portugese, and Morris Eller, through to the gangsters of Lawndale including the Miller brothers, Julius Anixter, and Benny Zuckerman. Then there’s the Syndicate strand that took over from them at the end of World War II, with figures like Lenny Patrick, David Yaras, Jack Guzik, and Frank Rosenthal, who oversaw crime in the Jewish districts and sometimes beyond. And finally, there’s the strand of Jewish politicians like Michael and Moe Rosenberg, Jacob Arvey, and Arthur Elrod who, with one foot in the world of crime and another in city and national politics, understood themselves as granting franchise rights to and relying on the services of the winners of those ongoing gangster feuds. Those three braids came together most crucially on January 14, 1944, when Zuckerman, the last undisputed boss of the independent Lawndale gangsters, was murdered, likely by Syndicate killers Patrick and Yaras, with the blessing of 24th Ward alderman Elrod. That watershed moment marked the end of a generation-long era in which various independent gangsters grew their operations until Zuckerman emerged as the ultimate boss of Chicago Jewish organized crime. It also marked the beginning of Patrick’s rise, the beginning of a half-century that would see him running many of those same operations as a functionary of the Syndicate rather than on his own. And it reflected one in a series of instances in which the politicians of Jewish Chicago demonstrated the degree to which their power grew out of an ongoing relationship with the gangsters of the community they served.

Connecting the Dots

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As a reflection of that fundamental thesis—the claim that the history of Chicago’s Jewish gangsters comes in strands that weave together to form the whole—I have organized this book in braids, in a series of chapters that work from specific anecdotes or character studies back to the central narrative. As I have come to see it, the story depends upon twisting ever more elements into the whole. This is, therefore, not simply a history of Chicago’s Jewish gangsters but also—like such recent studies as Rose Keefe’s The Man Who Got Away, Rich Lindberg’s Gangland Chicago, Robert Lombardo’s Organized Crime in Chicago, Mars Eghigian’s After Capone, and Louis Corsino’s The Neighborhood Outfit—a focus on a corner of Chicago’s organized crime that conventional Capone-centered histories overshadow. Understanding each piece of it, then, depends upon understanding a sense of the whole. I begin this story here with “the end,” with the moment when the independent Jewish gangster world of Benny Zuckerman was cut short by the power of the Syndicate that Lenny Patrick represented. Some chapters extend that story, chronicling Patrick’s subsequent career or, through what amount to flashbacks, give fuller context to Maxwell Street, Lawndale, and the gangsters—like my family—who shaped Zuckerman’s rise. Others weave in parallel concerns, like the shifting nature of organization in criminal Chicago, the rise of the Democratic political machine from its neighborhood origins, or the evolution of RICO as a law-enforcement technique and existential threat to the mob. I hope each chapter feels something like a new story, but I hope even more that each comes eventually to feel like an addition to the larger narrative. There’s a reason no one has yet written a full history of Chicago’s Jewish gangsters, of the world in which my grandfather found himself. That’s because the fragments of that history don’t fit neatly together. The organization here is both an acknowledgment of that challenge and a response to it. I’ve tried to focus on each of those fragments separately, to tell the stories of individuals or retrace the development of a particular trend and then, as part of such telling, to demonstrate how it weaves into the whole. I doubt any individual I deal with would have a sense that he served as a chapter in a longer history, but again, that’s part of my thesis: it’s taken us to the twenty-first century to get the necessary perspective on the way one character’s experience inflected the others’. It’s taken this long to answer my mother’s question, to see a single story in the sometimes only loosely connected stories of the Jews who made up Chicago’s representatives in the world of organized crime.

1 THE END, OR ZUKIE’S BAD DAY

I Benjamin Zuckerman was already having a bad day on January 14, 1944, when he arrived at his West Side home at 6:30 p.m. He’d spent the last few months worrying about a police crackdown on the gambling interests he controlled in the mostly Jewish Lawndale neighborhood, and things weren’t getting any better with the Chicago crime syndicate demanding that he double the share he paid for permission to operate.1 He’d recently gone back into the alcohol business, something he’d mostly left behind with the end of Prohibition.2 This time it was legal, but the competition was just as fierce, and he’d already stepped on the toes of at least one Syndicate big shot. To top it off, he’d been visited just that afternoon by three well-dressed men “with dark complexions,” who had kept him at his office at the Central-West Beer Distributors past the usual closing time.3 Zukie the Bookie—that was the name by which most of Chicago knew him— had survived a lot of bad days to get where he was. Early in Prohibition, he’d hooked up with gambling interests in the Jewish greater Lawndale area headed by Julius “Lovin’ Putty” Anixter, and he’d kept a level-enough head throughout the dangerous times that he wound up, eventually, assuming leadership of Anixter’s operation when the old man died a few months earlier. He’d nearly been killed seventeen years before in a drive-by shooting in front of his house on Lawndale Avenue,4 but that hadn’t been enough to drive him out of either the gambling or bootlegging businesses. He’d recovered and gone on to thrive in the kind of environment where you could get shot just walking down the street. Of course, by 1944 Zuckerman looked as if he had left behind most of the violence of his early days in the business. He had survived Prohibition and the

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bloody consolidation of booze and gambling operations in its aftermath, and he had grown from a dime-a-dozen thug into a successful businessman. Along with Ben Glazier and two other top lieutenants, Willie Tarsch and Louis Dann, he ran the lucrative, if harassed, gambling dens in and around the R&K restaurant in the heart of North Lawndale. He was a precinct captain for the Democratic party, and he had the ears of Jacob Arvey and Arthur X. Elrod, the two most powerful politicians in the 24th Ward and the leaders of what was arguably the most influential neighborhood political machine in Chicago. And he had achieved something close to a monopoly on organized gambling in the area. A generation earlier the leading Jewish gangsters running gambling in the neighborhood were Anixter and Davey Miller, whose headquarters had been in the building the R&K had taken over. Anixter had died in late 1943, however, and Miller was out of the rackets altogether. Where those two had competed, Zuckerman consolidated, and he ran things in the area without any immediate competition. In essence, what Zuckerman had accomplished—on his own and as Anixter’s right hand—was to stitch together a variety of different neighborhood criminal operations into one overall gangster business. By the standards of the larger Syndicate, the organized crime “mob” or “Outfit” that had grown out of the gang most famously headed by Al Capone, Zuckerman’s operation was small-time. By the standards of the Jewish community, however, it was substantial. In the early 1920s, when many of greater Lawndale’s Jews were newly settled and Prohibition was a recent phenomenon, there were dozens of small gangs competing for the booze market, for opportunities to run gambling dens, and for political and police favor. Those different gangs had gone head to head, and they often beat up and murdered one another. It was a brutal and violent era, and most of the young men who attempted to make a living through organized crime found it easier and wiser simply to walk away. Zuckerman had remained, however, and he had risen to the top of the neighborhood peak. There may have been more powerful gangsters in other parts of the city, but he had effectively conquered the local scene. He was the boss of Jewish Chicago as it concentrated in the greater Lawndale area. The home he walked toward that evening was a welcoming one. A mile and a half north of the chaotic and busy neighborhood where he made his living, it was on the kind of quiet street where John and William Carroll, eight- and elevenyear-old brothers, could play outside in the January dusk. It was a comfortable, middle-class community, the kind that would die out when Chicago’s suburbs siphoned away most of its residents in the years after World War II, but one that was prosperous and apparently safe. Although Zuckerman was forty-nine years

The End, or Zukie’s Bad Da

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old with a sixteen-year-old son, he had recently remarried, and he had a fifteenmonth-old daughter waiting for him. Life was, on balance, very good. So, when Zuckerman stepped out of his car and opened up his afternoon newspaper to scan it by the light of a street lamp, he must already have felt himself relaxing. His neighborhood must have seemed very far from the rough-and-tumble Maxwell Street of his early career, and it’s easy to imagine him feeling as if he were already in an entirely different world. Whatever hassles he had left behind were ones that he could forget for at least a little while as he enjoyed married life and the comfortable distractions of home. On Roosevelt Road, in front of his restaurant and gambling hall, he might have worried if he’d seen a car stop suddenly and heard a door swing open, but this was a different kind of neighborhood. This was not a place where gangsters did their business; it was the 1940s equivalent of a suburban subdivision. So he probably paid no attention to the slightly built man walking slowly in front of him. When Zuckerman paused over his newspaper, that man turned suddenly, drew a gun, and fired a bullet that hit Zuckerman in the chest. It was so sudden and out of place that William Carroll later told police, “We thought it was some kind of a game until we ran up and saw the blood.” According to one account, Zuckerman lay on his back in his own front yard, crying out, “Don’t shoot, don’t shoot.” The man nevertheless proceeded to fire two more times, hitting Zuckerman in the eye and in the throat, and then he stepped quickly into a car where two other men had been waiting to help him get away.5 The boldness it took to shoot a man at point blank range, and the careful choreography of the murder, marked it as the work of a professional killer, evidently a member of the Chicago Syndicate. This was gangster crime on a sophisticated level, and it heralded a clear shake-up in the gangster world. Things were going to change in the organized crime of Jewish Chicago, even if the changes were subtle enough that most of the people on the street wouldn’t recognize them. What certainly was not subtle was that, with those bullets, some powerful people had taken aim at the last independent Jewish gang in the city.

II Although Zuckerman’s murder was never officially solved, gangland rumor, police speculation, and later history make it seem likely that the killers were Lenny Patrick, David Yaras, and Eddie Murphy, a mostly Jewish syndicate hit squad just

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getting its start as some of the city’s most prolific mob killers. Patrick eventually succeeded Zuckerman as the most powerful gangster in Jewish Chicago, doing so as an agent of the Syndicate, however, rather than in Zuckerman’s independent fashion. Yaras would go on to become one of the country’s leading gangsters, serving as a key Chicago liaison to the Miami area and briefly mentoring Frank “Lefty” Rosenthal, the basis for Robert DeNiro’s character in the movie Casino. And Murphy, seemingly targeted for bigger things in the Syndicate as well, wound up murdered by his erstwhile partners six years later. The difference between Zuckerman’s operation and the Syndicate for which Patrick and Yaras fronted was essentially the difference between a neighborhood hardware store and the big-box superstores that dominate today’s malls. Zuckerman and his partners, as with his predecessors, were certainly connected to gangsters throughout the city and sometimes even across the country, but they functioned on their own, negotiating for inventory and political protection on their own terms and working from a defined neighborhood space. They had the “concession,” as Zuckerman himself described it,6 for their neighborhood in a federation of organized crime. Or as the Tribune put it in a 1941 exposé, they were “subcontractors” of “the big syndicate.”7 Their opportunities for profit were limited to the businesses and residents of the neighborhood. As the tastes and conditions in greater Lawndale changed, so did Zuckerman’s business. The more wealth and commerce there was in the neighborhood, the more chances he had to make money. When gambling profits fell off during World War II, however, Zuckerman returned to his bootlegging roots. He reportedly supplemented his core gambling business by pushing his liquor in the largely Italian American neighborhood to the east, which would have been a serious breach of gangland policy and a likely affront to syndicate figure Dago Lawrence Mangano, boss of the Near West Side. If Zuckerman had lived long enough to be involved in the North Lawndale of the late 1960s, when most of the neighborhood’s Jews and Jewish businesses had relocated to the North Side or the suburbs, he would have found changing demographics had essentially put him out of business. In contrast, the Syndicate dealt with organized crime of every variety and did so across the city and in many suburban areas. It was, in effect, a corporation of crime with broad-enough interests and wide-enough geographic influence that it could sustain itself across neighborhoods and generations. As with legal corporations it could overwhelm smaller neighborhood enterprises by calling on resources from its other operations. When changing fashions meant a particular neighborhood was no longer in vogue for nightclubs or illicit gambling, the

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Syndicate could open up new nightclubs and new gambling dens somewhere else. When police or political pressure grew threatening, it could move the focus of its operations elsewhere and continue just as efficiently. If it came time to kill a competitor or potential witness or to intimidate someone who had failed to pay off a debt, well, it had people who specialized in that sort of work too. In one famous case from 1924, when newly elected Chicago Mayor William Dever declared a war on gangster interests, representatives of the mob backed Joseph Klenha for president of the village board of suburban Cicero. Their campaign was blunt and unsubtle; they carried guns into polling places and roughed up voters whom they suspected were opposed to Klenha and the other candidates on their slate. They had an actual shootout with Chicago police, whom Dever had authorized to act outside Chicago city limits that day, and Capone’s brother Frank was killed in the confrontation. At the end of the day, the Syndicate won, however. With Klenha in control, Syndicate gangsters had a community where the government and its police were literally in business with them, and they had an area where they could concentrate their interests whenever law enforcement made it difficult to do business within Chicago itself.8 Cicero remained notoriously mobbed up for the rest of the twentieth century, something evident as recently as 2002, when town president Betty Loren-Maltese, widow of a known Syndicate gangster, was convicted on racketeering charges and estimated to have looted $12 million from the town.9 Fifteen years before Zuckerman’s murder, in the St. Valentine’s Day Massacre, the Capone mob had wiped out its major citywide competition, the North Side Gang established by Dean O’Banion and later headed by Bugs Moran. The North Siders, a mixed collection of Irish, Jews, Italians, and other ethnics, had gone head to head with the largely Italian Capone gang, trying to match them in the sale of booze, gambling, and labor racketeering and waging a long and bloody series of shootouts and assassinations. As the two sides clashed from roughly 1924 to 1931, introducing the world to drive-by shootings, tommy-guns, and the idea of “taking someone for a ride,” the city earned an international reputation for violence and gangster rule. It was a kind of war and, when the Capone gang cleared the battlefield and absorbed most of the North Side’s remaining operations, it emerged as the mature Syndicate, Chicago’s own commission of crime. Zuckerman and his gang represented a very different kind of obstacle. They did not set themselves up as challengers; Zuckerman, Glazier, Tarsch, and Dann knew they had no chance of surviving if they took aim at the interests of Capone’s successors. Instead, Zuckerman and his partners negotiated their place with the

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Syndicate. They didn’t compete with centralized organized crime; they subcontracted from it. They held what amounted to the franchise rights for gambling and some legal booze distribution in Lawndale so long as they abided by the Syndicate’s general wishes and paid off Syndicate representatives in the agreedupon ways. In assigning Patrick or another agent to murder Zuckerman, the Syndicate pulled off, so to speak, a hostile takeover. It removed Zuckerman as a middleman in its business dealings, and it pulled Jewish greater Lawndale into the efficient umbrella of organized crime that already covered most of the rest of Chicago. And few things could have been more efficient than the dispatching of Zuckerman and his partners. In a twist that would seem hard to believe if it happened in a Hollywood gangster movie, Ben Glazier was so shaken by the news of his old friend’s death that he suffered a fatal heart attack. As soon as he received the call, he told his wife he was off to see Zukie at the Garfield Park Hospital. When he took a while getting dressed, she looked in on him and found he’d collapsed, never to recover.10 The two partners were dead within an hour of each other. It was a literal case of frightening a man to death, and in this instance it made the Syndicate’s inevitable takeover of the Jewish West Side all the smoother. On the one hand, with Glazier gone there were fewer opportunities for the police to investigate a crime they could probably not have solved under the best circumstances. As Chicago police detective Timothy O’Connor said, “The one man who might have told us something—Glazier—is dead.”11 On the other, with the bullets fired at Zuckerman killing a second man who was miles away, the Syndicate seemed all the more invincible.

III Louis Dann, one of Zuckerman and Glazier’s two remaining partners, disappeared soon after Zuckerman’s murder. He saw the writing on the wall and fled for safety to California, but six months later, after former alderman Jacob Arvey, relying on a deep mixture of political and criminal connections, negotiated his safety,12 he returned to Chicago and stayed out of any serious criminal activity. For most of his later years, he lived, as longtime Chicago Sun-Times crime reporter Art Petacque put it, “the down-at-the-heel existence of a cab driver.” When he died in October 1950, he was fifty-six years old and remembered fondly by enough of his old friends that they chipped in to buy him a silver-lined coffin. It had been only

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six and a half years since he was one of the gambling kingpins of the West Side, but he seemed a relic of a bygone era.13 In his way, he was the last surviving remnant of the last significant independent Jewish gang in Chicago, but he died of natural causes, and his funeral elicited far more nostalgia than it did speculation about gangland politics or hidden criminal motives. That left, in the wake of Zuckerman’s murder, Willie Tarsch as the sole surviving boss of the Lawndale gang. Unlike Dann, he refused to give up, keeping the independent gang running largely on the strength of his own nerve. And Tarsch had a lot of nerve. He was, according to Police Captain Thomas Alcock, “one of the toughest boys ever to hit the street,”14 and several sources described him as a “hophead,” one who took opium twice a day.15 People regularly referred to him as “Galatz” or “Kolatch,” Yiddish for “mischief maker,” a nickname apparently bestowed on him as a child by his own mother when she grew frustrated by his refusal to follow rules.16 Lenny Patrick would later recall him as a chiseler, as someone who sometimes tried to use loaded dice to up the odds that his game would bring in more money.17 He had a history in organized crime going back at least to the late 1920s, when he’d helped smuggle booze in from Canada with some of Bugs Moran’s North Siders, so he’d experienced gangster upheaval before.18 He didn’t have the range of Zuckerman’s political connections, though, and that meant his standing was precarious. He was even more of an independent operator, even more at the mercy of the heavy hitters of other organized-crime operations. Tarsch continued to run gambling houses, maintaining the R&K restaurant and several rooms in the nearby blocks. He also remained a gambling power with at least some area bookies continuing to pay him tribute. Some of those bookies apparently grew nervous about how to cast their allegiance; some sensed the Syndicate was likely to win out while others reasoned they should stick with the organization they’d always known. Gambler Norton Polsky, for instance, admitted to his girlfriend that Zuckerman’s murder left him unsure where he himself stood.19 The chips may have been stacked against Tarsch, but he was fearless, and he represented the way things had been done in Lawndale for a generation: Jewish bookies buying their protection from the local Jewish gang. It’s likely Tarsch heard overtures, if not directly from the Syndicate bosses, who would send Patrick and Yaras, then from his longtime political allies in the 24th Ward Democratic machine. Like Zuckerman before him, he owed his position as gambling boss to his strategic connections with the neighborhood branch of the machine. Tarsch had helped Anixter and Zuckerman deliver votes and had even

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been a precinct captain in recent years,20 but he hadn’t been as central in that process. His partners had been rewarded the right to sell protection from the police; all he could do was try to hold onto it. He could probably have cut a deal, could probably have agreed to surrender a higher slice of the profits, or more dramatically, agreed to quit altogether. Murder could be a messy and expensive business, and there must have been gangster powers who would willingly have accepted from him the kind of retirement to which Dann had acquiesced. Over time Tarsch must have sensed the weakening of one after another of the props supporting him. His gambling returns likely dwindled as bookies discovered he couldn’t enforce his hold as effectively. He probably grew increasingly frustrated with what he heard from the men to whom he’d been paying money over the years. Alderman Arthur Elrod of the 24th Ward had his own long and shady history, but he’d emerged as the political boss of the neighborhood, the central link in the chain that connected the Syndicate, the police, and Tarsch’s operations. Tarsch certainly tried to explain the situation to Elrod, petitioned him to enforce the system of payoffs and protection that had been the way of Jewish Lawndale since the dawn of Prohibition. Elrod may have pushed back, or he may have stalled, but he knew the Syndicate wasn’t about to settle for a smaller portion of the neighborhood’s profits. Then it all came to a head. As investigative journalist Ovid Demaris put it—citing a 1969 “secret government report”—unnamed Syndicate figures complained to Elrod in early 1945 that Tarsch was impossible to work with. Elrod, in Caesar fashion, indicated he was withdrawing his political protection and said, “Take care of it in your own way.”21 On April 6, 1945, fifteen months after Zuckerman’s murder, Tarsch was playing “short cards”—a version of gin rummy22—in a room next door to the Lawndale Restaurant, a half mile west of the R&K, where Patrick would soon set up his own local headquarters. He must have been watching his back at all times, and he’d constructed an elaborate set of precautions. When an unidentified man called the Lawndale asking for him, the restaurant owner, Nathan Tardasch, slipped between two side doors and a gangway to pass along the message. Tarsch, seemingly cool, finished his hand and ducked out to cross the gangway himself. He must have assumed he was in the clear; after all, most Chicago gangways are only a few feet wide and they’re invisible from the street. The call was compelling; he trusted the man bearing the message. What, then, was there to worry about? Tarsch probably never heard the shotgun blasts that shattered his skull. Police recovered three spent cartridges, a number reminiscent of the manner

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of Zuckerman’s death.23 They also found, just beyond his outstretched hand, a penny—seemingly a sign that he was a cheapskate for passing up the chance to make a real deal.24 It was, the details suggested, another Syndicate job, efficient and well planned; and it was, this time by his own eventual admission, Lenny Patrick’s handiwork.25 Given the peculiar place for the ambush, it’s clear that somebody Tarsch trusted had had a hand in setting him up, but even decades later it’s impossible to guess who that might have been. With the sea change taking place all around him, with the collapse of Lawndale as a place that could support an independent gangster operation, there must have been dozens of people willing to sell him out to curry favor with the Syndicate. Tarsch, forty-five years old, left behind three children, but in a criminal sense he had no heirs. Organized crime in Chicago may still have involved plenty of Jews, but it stopped being a Jewish business with his murder. He was the last man standing from the Benny Zuckerman gang, and after him there was room only for another Syndicate operation and not for the independent Jewish operation that had characterized Lawndale since it became a Jewish area. He still had his supporters, still had bookies and sluggers who’d have preferred not to work with the Syndicate directly, but he was the last one able to organize them. His murder, coming on the heels of Zuckerman’s, placed another piece of the city— the last independent Jewish piece of it—under the direction of the city’s Italian American–dominated gang. If those two murders marked the end of one tradition, however, they also marked the start of another. With the independents out of the way, Lenny Patrick had a clear field to impose a different sort of gangster rule, one he maintained for close to half a century. As one of the most prominent Jewish faces of the Syndicate in the years after World War II, he helped develop the vicious juice loan rackets, extorted legitimate businesses of their profits, maintained multiple networks of bookies and betting handbooks, and became one of the Syndicate’s most reliable killers. It would take a lifetime, a very long lifetime, before he answered for his role in the killings of Zuckerman and Tarsch and for his part in sustaining the machinery of the greater Syndicate. And then, in a way no one could have foreseen, Patrick would be called upon to tell his story in a pair of trials that would bring down much of the Syndicate he had spent his lifetime serving.

2 BEYOND SCARFACE, A KOSHER CAPONE FOR MAXWELL STREET

I In 1932 screenwriter Ben Hecht faced a challenge. He’d been hired to adapt the 1929 novel Scarface into a film. The novel was clearly modeled on the public image of Al Capone, himself a scar-faced gangster who rose to rule Chicago organized crime. But, despite some impressive moments, the novel was a mess. It featured an impossible plot twist where the antihero’s brother, gone from the family for years and established as a cop, returns at the end and kills him in a case of semi-mistaken identity.1 Hecht didn’t want such melodrama; he wanted instead to show the color of the gangster world he knew firsthand as an acquaintance of Capone and many of the other players in the early years of Prohibition Chicago.2 He wanted to tell a story that explained the rivalries among the gangster characters who made their way into the headlines, shooting someone or getting shot and then vanishing into obscurity. He wanted to make sense of what seemed, from the evidence of different screaming headlines every day, an incoherent world of crime. The story that Hecht gave us in the movie Scarface continues, in many cases, to shape the history we tell of the Chicago gangster. It was, as historian David Ruth puts it, an effort to present an “imagined gangster”3 as a figure who was more than simply a criminal, but a sign of the complications and contradictions of the modern city. Hecht wasn’t faithful to history as he depicted his Capone character’s rise, but he borrowed generously from the headlines. The brazen Scarface—whether we call him Capone or Camonte as the film does—first emerges as the lieutenant to a lieutenant: in the film Johnny Lovo, in real life Johnny Torrio. That lieutenant

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kills his own boss, Big Louis Costillo/Big Jim Colosimo, and the emboldened gang goes on to kill its tough nemeses on the North Side, the florist gangster O’Hara/ O’Banion and the clever Gaffney/Weiss, culminating in its takeover of gangland with a massacre in a garage on St. Valentine’s Day. Hecht added a Lucrezia Borgia– inspired incest plot and created a cinema archetype in George Raft’s oh-so-cool coin-tossing Guino Rinaldo, but the upshot of the film was to establish the history of Chicago gangland as the story of one man’s violent rise. As Camonte says in the film, while waving a gun, “Do it first. Do it youself [sic]. And keep on doing it.” Almost ninety years later the success of the story that Hecht and his collaborators gave us obscures the more complicated history it sat atop.4 As it happened, the gang Capone led did go on to become the foundation of the Syndicate, which would run organized crime for the rest of the century, but Capone neither founded that gang nor ran it during its most sustained success. And for most of Capone’s period, his gang was only one piece in a larger alliance, or “combination,” of Chicago’s gangster world. The real story behind organized crime in the era was less the one about a tommy-gun–toting Scarface and more about a prime ministerial Johnny Torrio and his intermittent success in working with the ambassadors of other gangs.5 As historians Humbert Nelli, Alan Block, and Gus Lombardo have shown, it was less about killing one another’s rivals—although it had quite a lot of that—and more about creating a citywide network of alcohol distribution and gambling concessions that licensed some competitors while shutting everyone else out.6 It works less well on film, but the story of the 1920s Chicago gangster was mostly about confederation, about taming a Wild-West industry open to anyone with guts and a gun into something that a handful of powerful interests could control. Hard as it may be to believe in retrospect, organized-crime peace talks produced news, and reporters wrote knowledgeably about the outcome as competing gangs adjudicated the boundaries between their territories.7 By 1926 there was even a map, compiled by noted University of Chicago sociologist Frederick Thrasher, showing each gang’s area of control.8 In the case of a series of 1926 peace conferences convened in the wake of the murders of North Side bosses Dean O’Banion and Hymie Weiss and the serious wounding of Torrio himself, a number of participants gave statements to the press, keeping reporters up to date on negotiations for the “armistice.”9 A similar conference in 1929 took place in Atlantic City, no doubt to dampen publicity, but word leaked out immediately in any case.10 And Judge John H. Lyle, famous for being tough on the mobs, claimed he’d actually been approached by “a well-known Loop character” to serve as

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adjudicator for one such conference since his straight-up reputation was guarantee of his impartiality.11 This wasn’t a story that Ben Hecht could do much with; it’s perhaps best told in another book released the same year as Scarface, John Landesco’s Illinois Crime Survey, with its extensive look at how gangsters of the era came to cooperate with one another, but no one has found a way to turn that catalog into a Hollywood film. As it was, each such treaty wound up broken in some fashion, but the process of increasing confederation was a more accurate representation of the way organized crime came to assert control over Chicago than the biography of any one figure.12 The bottom line of all such negotiations was that some were in and some were out. If you got a piece of the bootlegging pie, you had a stake in keeping the entire operation as it was. The great crisis in Torrio’s original plan came when O’Banion, boss of the second-largest gang in the confederation, decided he wanted more and, in a complicated transaction, sold Torrio ownership in a brewery he knew was about to be raided, resulting in Torrio’s arrest in May 1924.13 That precipitated a brutal gang war that climaxed in the St. Valentine’s Day Massacre five years later, set the backdrop for the “Scarface” side of history, and amplified the notion that hotheads could put their self-interest ahead of the collective business. While such conflict got the lion’s share of reporting and storytelling, the real story happened underneath the headlines: more and more participants had incentive to play ball with the Capone gang as it matured into the Syndicate. It had the resources, and it had the power to punish if you crossed its bosses. So long as you played by its rules, you got to stay in the game. Until, that is, the rules changed. Benny Zuckerman’s story, a story stacked on top of the stories of Putty Anixter, Davey Miller, and the other gangsters of Jewish Chicago, was one chapter in the larger history of confederation. As Anixter’s lieutenant and then as the boss in his own right, he won the franchise to pursue organized crime in Lawndale so long as he didn’t rock the larger boat. He could sell booze, oversee gambling, and squeeze out whatever other profits were available. His gang emerged from a series of neighborhood predecessors who, defeating or absorbing one another, coalesced into a clear group with a distinct headquarters on Roosevelt Road. He worked for and with local machine politicians like Moe Rosenberg, Jacob Arvey, and Arthur Elrod, and, while he would certainly have had to answer to the Syndicate big shots, he had a measure of autonomy. Jewish greater Lawndale was far enough from downtown, far enough from the offices of Capone and his successors, that it fit only loosely into the larger whole.

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When alcohol became legal again, however, things began to tighten up. The vast profits from bootlegging went dry more slowly than we might imagine today—early post-Volstead distribution was still highly controlled and there were substantial profits from finagling taxes on legal alcohol14—but as they diminished, the dynamic within the collective changed. The Syndicate bosses simply had less reason to tolerate a system of client-partners who, in effect, were less efficient at generating profits. Under the new rules, Zuckerman was no longer the equivalent of a franchise holder in an out-of-the-way district. He was a middle manager in an industry that, until it would more fully exploit the possibilities of gambling and racketeering in the years after World War II, was under pressure to shore up its profits.15 That’s where the story of Lenny Patrick begins. As someone of Jewish Lawndale, yet excluded from the real riches, he was the perfect hammer to take out the independent Jewish gangsters. Zuckerman may have died in a scene out of Scarface, but the bosses behind Patrick and Yaras were businessmen first. They directed the killers for long-term financial gain, in a way that would give them greater leverage over the city than the then-quarter-century-old model Torrio had first shown them. It was the start of a different story, one that has yet to find its Ben Hecht.16 And, of course, it was the end of Zuckerman’s story. Once the Syndicate decided to replace the confederation model with the corporate one, there simply wasn’t room for him anymore.

II On a smaller scale Jules Portugese was a Jewish Scarface, a Kosher Capone on Maxwell Street, if you will, an example of the left-behind gangsters as the confederation sorted its winners from the other losers. He was one of those tough guys who rolled the dice with his life as he tried to graduate from small-time crime into the big money. Like Zuckerman at the same time, and Patrick half a generation later, he got off to a bold start and then encountered the power of the Syndicate as an organizing force in crime. Like both, he came to understand the rules he was supposed to play by. Unlike them, though, he couldn’t establish a place for himself within that larger confederation. He started as a young man on Maxwell Street, a kid really, in a neighborhood without the burgeoning possibilities of North Lawndale and the rest of the Jewish far West Side, and he never got much farther than that. Still, he gave it quite a ride, and his story

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shows some of the hurdles that Zuckerman and Patrick overcame as they made themselves gangster powers in Jewish Chicago. The Maxwell Street of Portugese’s youth gave him an early education in toughness. The crowded neighborhood was the Chicago equivalent of New York’s Lower East Side, an immigrant-dominated place that Irving Cutler described as “a teeming, transplanted Eastern European shtetl atmosphere.”17 It was filled with pushcart peddlers, garment-shop workers, housewives struggling to raise large families on limited incomes, and eventually crime. In the late nineteenth century Maxwell Street may have been noted for its few bars relative to other ethnic communities, but that had changed by the time Portugese came along.18 For most of the time between the Great Chicago Fire of 1871 and the middle 1910s, Chicago had a well-established pattern of organized crime: it was tolerated so long as its bosses paid the established graft and stayed in strictly defined spaces, most often a neighborhood on the Near South Side called the Levee.19 Thanks to the same morality crusades that brought about Prohibition a few years later, however, that system broke down between 1912 and 1915, resulting in a succession of events, each touted as “the closing of the levee.”20 As a consequence, organized crime migrated into ethnic neighborhoods like Maxwell Street and the African American 2nd Ward as places sufficiently “foreign” (in the eyes of the generally white and Protestant reformers) to conceal gambling and prostitution from reformers’ prying eyes. Portugese became an adolescent just as those transplanted gambling, drinking, and vice institutions emerged in his community. Even that crime, the organized crime of mid-1910s Maxwell Street, had a measure of confederation. If you didn’t have the connections, you didn’t make it. For instance, Davey Miller’s brother Hirschie, who would go on to a spectacular career in bootlegging and racketeering, was only twenty-three years old in 191521 when he tried to establish a poolroom—and presumably gambling site—at 918 W. Maxwell Street. It was shut down almost immediately for lack of a proper license, a problem he attributed to “politics.”22 In contrast, several other places flourished in the area because they managed to obtain the blessing of one or another area politician. On July 19, 1913, with crime in the area jumping dramatically, the editors of the Jewish Record complained about what they saw on Maxwell Street. “There is not a shadow of a doubt there are gambling nests on the West Side. There is not a shadow of a doubt there are many houses of prostitution on the West Side. Some of these parade vice openly, others secretly. The places are under the protection of the lowest class of politicians.”23

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The Chicago Tribune, always a Republican Party organ and at the time an enthusiastic endorser of a progressive political movement at odds with machine politics, jumped into the battle to shut down gambling and vice displaced from the Levee with a series of exposés of specific nuisance houses and their suspected links to a larger structure of organized crime. One of the newspaper’s favorite tricks was to send a photographer to a particularly busy place, who would then, without warning, snap a flash photograph that would give evidence of the size of the crowd.24 On at least two occasions that sparked riots that left the photographers or their companions hospitalized.25 The paper was particularly concerned about Larman’s at 813 Maxwell Street, where their reporter claimed to see more than 100 young men taking part in craps and stuss games so elaborate that it required a staff of eleven to keep them running.26 According to the report, Frank Larman collected a nickel off each throw of the dice and another nickel from the one fading the throw, meaning a profit of ten cents no matter the outcome.27 The Tribune seemed to love showing the exotic—read “strangely Jewish”— nature of the places it set out to expose. In one of its lengthier pieces, it enumerated a number of the unusual names its reporter encountered: Fly Nick, Fat Morris, Skinny Harris, and someone called only Squint.28 It complained as well about how rigged things were in favor of making a profit for the ultimate backers, noting that the game at 1641 Taylor paid out only 33.3 percent of its take and claiming that Sam Davis, owner of “one of the biggest and best paying crap games in Chicago” had to pay 40 percent of his profits “to someone ‘higher up,’ ”29 The paper was particularly disappointed when its reporter followed police on a raid at Larman’s in 1914, only to find the boys had been tipped off. Instead of gambling, they found a noted stuss dealer named Godalia the Bum just finishing a demonstration of a trick pool shot. Intimating the open secret of the raid’s tip-off, he reportedly said, “There’s only one way to make a shot like this, and it’s got to be the way I tips you.”30 That was the Maxwell Street world of the adolescent Jules Portugese—as well as of the adolescent Benny Zuckerman and the young Lenny Patrick—and it taught him early that it paid to take chances. While still a teenager, he boxed under the name Jimmy Wells31 and soon found himself at the head of a gang of boys his own age. It’s likely—though hard to pinpoint—that he found ways to make a buck in the early days of Prohibition, when it was relatively easy to get hold of a stash of alcohol and then find willing buyers. The first time he made the newspapers was for just that sort of bootleg piracy but with a particular Jewish twist. On Saturday, September 25, 1924—Shabbos, no less—Portugese and his gang hijacked a truck carrying 140 gallons of sacramental wine, legal for religious purposes, provided a

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rabbi could demonstrate the proper paperwork. They were bold about it, forcing the driver out of the cab at gunpoint and then driving off in a separate car—but they were stupid too. The car’s plates were easily visible, the driver memorized them, and police recovered the wine that evening.32 Bush league as the heist might sound, it did have a few elements of the big time. First, it was clearly an organized gang including Sam Kaplan, Max Weiner, and Adam Haidelovich. Second, police located the bulk of the wine from Haidelovich’s garage at 2333 West Washington, which means at least one of them owned real property. And third, the guys managed to avoid conviction even though they’d been caught red-handed. That meant they had the connections—the “juice,” we might say—to line up the right lawyers and land in the right court. Clumsy and freelance as the operation may have been, it showed that Portugese had at least some license from the big boys. Further evidence of those connections came in the company he kept when he did spend time in jail. During his periodic incarcerations, generally lasting less than a week, he was a regular guest in fellow-prisoner Frank McErlane’s cell. The South Side gang boss was a major figure in the conflicts and alliances between the Capone gang and the North Siders and, according to historian John Binder, was the first gangster ever to use a Thompson submachine gun, one reason the Tribune called him “the most vicious killer in the country.”33 McErlane was part of the gangster elite so, when he did time, he could arrange for what he wanted. In this instance some of his underlings rented an apartment across from the jail and sent alcohol over through a system of rubber tubes feeding into hot-water bottles, which were then carried into individual cells. Supposedly, “One whistle from the jail cells brought whisky, and two whistles brought beer.” The story, which made the New York Times as well as the local papers, described Portugese as “stiff drunk” when guards thought to return him to his own cell.34 Most tellingly, Portugese had a minor role in one of the most spectacular killings in Prohibition history. After Dean O’Banion broke the peace that Torrio had brokered to federate booze sales across the city, the Torrio-Capone crew escalated the showdown by shooting O’Banion to death in his flower shop on the North Side. That effectively began the gangster war that climaxed in the St. Valentine’s Day Massacre. O’Banion’s murder is officially unsolved—though theories of who pulled the trigger abound35—but witnesses were clear in reporting that three men were responsible—one restraining O’Banion’s arm in a prolonged handshake and the others shooting him point-blank—and that they escaped in a waiting car. Portugese may have learned something about hiding his license plate from

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his wine caper, but police still traced the getaway car to him and his father. He claimed it had been stolen, but it stretches the imagination to think the killers would have happened to take a car belonging to someone so closely connected to them. As a frustrated Chief of Detectives Michael Hughes put it when the investigation moved slowly, “At least eleven men know who killed O’Banion and why.”36 So saying, he seemed clearly to refer to Portugese and his father, at the time the only people in custody over the murder. But getting to the fringes of the gangster confederation wasn’t the same thing as establishing a clear hold. One crucial difference between Portugese’s Maxwell Street and Zuckerman’s Jewish Lawndale was that Zuckerman’s world was full of fresh opportunities. By the start of Prohibition in 1919, the territories and graft of Maxwell Street were already carved up. Portugese’s father had a small place,37 as did Davey Miller’s brother-in-law Harry Block,38 but just as the lawns of greater Lawndale were wider and greener than the streets in front of Maxwell Street’s tenements, so were the criminal opportunities. Those small places sold a little booze and took in various amounts through gambling, but they didn’t lend themselves to expansion the way the Lawndale gangsters’ places did. There was competition in Jewish Lawndale, too, enough of it that a hired gun like Zuckerman had plenty of work, but it was a competition for a growing market rather than a mature one.39 Portugese clearly tried to establish his own franchise, his own area of influence, but he never succeeded. In retrospect, for instance, it’s difficult to trace his shifting allegiance. His involvement in O’Banion’s murder, or at least his car’s, puts him on the side of the Torrio-Capone group, as does his later association with Myles O’Donnell, a key far-west-side Capone ally.40 On the other hand, his involvement in a robbery with Vincent “Schemer” Drucci, a chief O’Banion lieutenant, as well as his friendship with McErlane, puts him on the other side.41 That seems to have established him as a kind of either/or, an experienced hand occupying a no-man’sland in the escalating war between the Capone crew and the North Siders, and he may well have been able to turn that loyalty-for-sale into opportunity. He could briefly play one side against the other. The steady money of overseeing gambling or brokering whiskey or beer never came, though. In the early years of Prohibition, Portugese made his money as a hijacker, by stealing someone else’s supply or, since there was no surer way to get yourself killed than to try that against Syndicate or North Side figures, to finding out-of-the-way opportunities such as the kosher wine heist. In one such case on January 16, 1925, he and three others held a gun to the driver of a truck carrying

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twelve cases of whiskey. In keeping with a theme of Portugese’s ill-fated career, the hijackers couldn’t get the truck to start, so they towed it behind their own vehicle, making it easy for the police to follow them to the Lawndale-area garage they’d arranged for stashing it. One man, Joseph Flack, was shot, and Portugese was caught after a policeman found him hiding behind a fence.42 How he got off that particular charge isn’t clear, but it was evidence that crime involving the combustion engine was a tough way for him to make a living. Police implicated him in another such attempt just days before he died, when it appeared that he and the North Side boss, Drucci, coincidentally set out to rob the same bootlegger at the same time. Portugese got away with the entire haul, which police thought might have been the reason he was soon killed.43 With hijacking so difficult, Portugese switched to the equally desperate business of stealing jewelry. His biggest haul came when he snatched $300,000 from a salesman in the Loop, but it was also likely his fatal mistake. Police caught him at the corner of State and Adams after a chase on foot, and this was one charge he couldn’t get out of.44 He pulled all his usual strings, but this time they didn’t work. As the Tribune put it, “Since the arrest of the well known police character[,] friends have been making frantic efforts to get him from police custody,” including issuing a writ of habeas corpus and petitioning for reduced bail. He wound up with a year’s sentence.45 The pressure of raising money to alleviate that trouble almost certainly contributed to his trying further crimes, including an $80,000 haul of gems from a guest at the Congress Hotel—a robbery he committed within days of the booze job with Drucci.46 He was, to say the least, a busy guy. In the end, though, the back-and-forth alliances and the last wild spree of crimes suggest the simple truth that Portugese never found a steady place in the confederation. He was too reckless, too much his own man, to become, like a Benny Zuckerman, an effective boss in Jewish organized crime. Or, perhaps better said, he was a Zuckerman of an earlier moment, a victim of organized crime’s changing rules two decades before that later change resulted in Zuckerman’s own murder. On July 14, 1926, police found his body along Milwaukee Avenue in suburban Niles after he’d been shot and tossed from a moving car. By coincidence, as with Zuckerman’s own murder, it was two boys who first saw the dead body.47 As the lead to the Tribune story put it, “Society had decreed Jules Portugese an outlaw and had sentenced him to prison, but certain of his fellow outlaws decided otherwise and yesterday he was doomed as an outlaw among outlaws.”48 The murder, naturally, remains officially unsolved.

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III The end of Jules Portugese’s story, however, like the end of Benny Zuckerman’s, also marked one beginning of the challenge of telling the story of the Chicago Jewish gangster in a coherent way. Portugese was more famous in death than he was in life—at least judging from newspaper coverage of him—and he briefly became a lens through which outsiders tried to make sense of the world in which he’d temporarily flourished. At least some observers tried to cast him as a prototypical version of what was taking place across Jewish Chicago. The year 1926 was part of the peak of the Prohibition Wars, and Portugese struck some as an archetypal casualty of the Scarface kind, one more urban desperado who shot others until he got shot himself. The Tribune’s story on his murder put it as awkwardly as it did because, while its author glimpsed that organized crime was transforming, the only story it could readily tell was the one about the losers in that transformation. For them, Portugese was an outlaw outlawed by outlaws for breaking the inscrutable laws of those outlaws. That doesn’t quite make sense, of course, but its confusion demonstrates an anxiety over not having a full understanding of the ways in which the changing structure of organized crime was undermining the gangster story most contemporary media had been telling. David Ruth elaborates this notion in his study of how Prohibition-era writers imagined the gangster figure. He argues that such writers were torn over whether to blame the gangsters for the violence of gang warfare or to see them as victims of it. As he put it, such authors were “divided most significantly, and most contentiously, over whether the typical criminal was responsible for his actions and whether he resembled ‘ordinary’ (native-born, middle-class) Americans.”49 In the case of the newspaper stories about Portugese’s murder, we see that divide clearly. Portugese was cast both as a cause and an effect of his circumstances, with the result that he never quite settled into either role. That moment of uncertainty in how to tell his early story mirrors the uncertainty that has made it so challenging to see a coherent account for Chicago’s Jewish gangsters across the twentieth century. The structures of organized crime were changing, and Portugese was a victim of that change. At the same time, the Chicago Jewish community was transforming as the center of gravity moved from the Near West Side of Maxwell Street to the far West Side of greater Lawndale. Both of those factors played into Portugese’s murder. On the one hand, he could not establish a sufficient criminal foothold in a neighborhood with shrinking opportunities. On the other, given those limits, he eventually had to cross the Syndicate or give up crime. Since he

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persisted, it meant his death. Those conflicting pressures made it particularly difficult to tell a consistent narrative. The Herald-Examiner inadvertently demonstrated how hard it could be to tell such a story. In a bid for sympathy for a ghetto boy gone wrong, it sent its reporter to cover Portugese’s funeral. The result was a tableau: Weeping women and the solemn sonority of deep-toned prayers. A room crowded with the new and old—bearded men wearing derby hats, stolidly staring before them, and dapper, smooth-shaven young men, Americanized to the nth degree, the new generations, and up front, a casket of oxidized metal, banked with flowers, Half [sic] lights and fitful shadows. So passed Jules Portugese, gangster, gunman, bootlegger, and jewel thief. The services were held at Piser’s undertaking rooms, 3111 W. Roosevelt road, and, in accordance with Jewish tradition, were conducted by the slain gangster’s father, Harry Portugese. Uncompromising, stern, the father, black-bearded, stood by the casket and intoned the solemn prayers of his creed. Then the casket was placed in a hearse followed by about twenty other cars.50

The article is an affecting one, reflecting less the “Chicago bang-bang” adrenaline of Scarface and more the saccharine of The Jazz Singer, famous as the first “talkie” motion picture and released in 1927, only a year after Portugese’s murder. It lays out the pathos of the immigrant experience, contrasting the greenhorn father with the son who grabbed too passionately for the promise of a new America. And, as it happens, it’s almost entirely wrong. To begin with, it is not Jewish custom for a father to lead prayers over the body of a deceased child. It surely falls to a parent to say kaddish, and some grieving parents might do more, but there was nothing traditional about the occasion if Harry Portugese did indeed lead the services. Harry may have been at the head of the room reading, but that hardly means he directed the proceedings. Whoever the reporter was, he or she almost certainly did not understand Hebrew and seems to have gotten lost trying to follow the service. In addition, a truly traditional Jewish service would have had a wooden casket rather than the striking metal one described. Again, the reporter could hardly understand the implications of such a departure from tradition along those lines, but it underscores the fact that—for all the poetic sense of the moment—he or she had very little idea what was actually taking place.

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The most significant mistake, though, turned on a misunderstanding of the Portugese family itself. Harry was hardly a classic Old World father adrift in an America of declining moral values and unable to make himself fully understood through a thick accent and thicker beard. Instead, as his arrest after the O’Banion murder suggests, he was a notorious saloon owner and a player in gangland proceedings of the day. Their home at Fourteenth and Newberry would have put them in the middle of the gambling-infested area that the Tribune had been highlighting in its reporting in the early 1910s.51 Far from an innocent, Harry was enmeshed in the system of graft that had flourished for at least the last decade around Maxwell Street. In a modest way he fit into pre-Prohibition’s confederation of crime, and he no doubt showed his son the rules of that game. That is, his history flips the story’s image of Jules Portugese on its head; the younger man wasn’t so much a ghetto boy gone bad as a born-and-bred gangster whose opportunities were shrinking. Harry Portugese’s own story became all the clearer a year and a half later, when he was murdered on New Year’s Eve, just before the start of 1928. Some time that evening an apparent jewelry salesman entered his restaurant—located then at 1300 Jefferson—and began to quarrel. The Tribune reported that police were looking into allegations that Harry had acted as a fence for jewel thieves, which suggests, if true, that he may have been behind Jules’s late-career exploits. The unidentified salesman suddenly pulled out a knife and stabbed him. Harry managed to draw a gun and fire a few stray shots before collapsing, but he never recovered. That detail alone underscores how different he was from the Herald-Examiner’s portrait: It’s a safe bet that few traditional Jewish fathers of the day were packing. In the end it doesn’t seem an exaggeration to describe the Portugeses as a Mom-and-Pop outfit trying to make a go of it in an industry where franchises like Zuckerman’s were starting to emerge. Barring the occasional end-of-the-newsstory reference, however, Jules Portugese and his family were pretty clearly “out” by the late 1920s. In his way Jules represented the likeliest ambassador from the Maxwell Street gangster world to the rising confederation the Capone gang was shaping. He had the guts, and he had the ambition, but, on top of lacking luck, he came from the wrong place to make it happen. Zuckerman and Patrick had largely abandoned Maxwell Street for the promises of Jewish Lawndale. Portugese kept his headquarters in the old neighborhood, in a place stuck in a model of crime that couldn’t last through the decade. It’s not hard to see how things could have been different for him, how he might have held the power that Zuckerman came to hold if, say, the North Siders had held out longer against Capone or if he could have escaped capture in his jewel heist, but all we have is what really happened.

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He was a Jewish Scarface, a shoot-’em-up antihero for a couple months’ worth of headlines that obscured the larger story of the confederation taking place around his misadventures. And then he was gone, replaced in the history of Chicago’s Jewish gangsters by the likes of Benny Zuckerman, who thrived in such confederation and, in turn, by Lenny Patrick, who made his biggest mark by embracing the even more tightly organized Outfit that came later.

3 THE SUNSET OF 1974: LENNY PATRICK’S CHANGING WORLD

I By 1974 you could forgive Lenny Patrick a little paranoia. He’d been the boss of Syndicate gambling in Jewish Chicago since Benny Zuckerman’s murder twenty-five years before. Everyone knew that and, for practical purposes, such knowledge mattered. It meant people made way for him, that they understood he had influence to help in shady business, and that they acceded to his suggestions, requests, or threats. In a legal sense, though, the difference between knowledge and proof was everything. Until law enforcement had hard evidence against him, he was a free man. And by 1974 the FBI and Chicago Police Department had been trying to collect such evidence for at least fifteen years through sustained campaigns of surveillance, wiretapping, and harassment. Wherever Patrick went, someone was trying to track him. He’d had a long run as boss of Chicago Jewish organized crime, but the net was tightening around him. As far back as January 1958,1 the FBI regarded Patrick as potentially one of the core leaders of the Chicago Syndicate. J. Edgar Hoover’s Bureau was notoriously slow in focusing its resources on organized crime. As many histories have argued, Hoover long regarded communist conspiracy as the central threat to American democracy, and it wasn’t until the middle 1950s—when a pair of explosive Senate hearings led by Estes Kefauver and then John McClellan gave a hint of the scope of national collusion in racketeering, labor shakedowns, and gambling—that he was persuaded to change.2 For years after, the FBI was playing catch-up to what many local law-enforcement officials, newspaper reporters, and guys-on-the-corner already claimed to know.

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As longtime agent William Roemer recounts, when the Chicago office of the Bureau first began its investigations in earnest in 1959, Patrick was one of the ten suspects targeted in the “top hoodlum program,” which meant he was followed for long stretches by agents charged with learning everything they could about him. Patrick was dropped from that top tier of suspects within a year or two, when agents determined that he answered to others more than called the shots, but he remained in the scope of the investigation. For what it’s worth, Roemer himself was assigned to learn everything he could about one of Patrick’s closest colleagues, a Greek American “fixer” named Gus Alex.3 The idea was to get as much information as possible, of course, but it was also about putting the mobsters under pressure, complicating the way they did business. As a result, Patrick and the rest of Chicago’s gangster elite learned more and more discretion. For instance, after Tony Accardo built his dream house in 1963, he had his architect murdered to ensure his privacy. Accardo, regarded by consensus as the ultimate boss of the Syndicate, commissioned a luxurious but understated home at 1407 N. Ashland Avenue in the wealthy suburb of River Forest. It included a basement accessible only through a staircase that began at the back of a closet and featured a meeting room with a built-in roundtable large enough to convene a board of directors.4 During construction, Accardo, despite being observed on site, denied that he was the purchaser.5 FBI agents approached Sam Panveno, who worked under the name Van Corbin, attempting to obtain blueprints for the house with an eye toward a potential wiretap. Police found Panveno’s body on July 20, 1966, after he was murdered, apparently by Syndicate killers.6 Getting away from law enforcement’s prying eyes mattered too much to leave anything to chance. In a less grisly example, Chicago police investigators with the C-5 crime unit discovered that Patrick and several other high-level Syndicate figures were trying to avoid publicity by meeting at the Luxor steam baths on the near Northwest Side at 2039 W. North Ave. Joey “Doves” Aiuppa, one in a succession of bosses that Accardo charged with running day-to-day business after the fall of the more notorious Sam Giancana, would stop in alongside prominent mobsters like Marshall Caifano and Joey Glimco. Undercover C-5 agents insinuated themselves as other patrons, who, in the words of Tribune reporter George Bliss, “seemed to be dozing [but] actually were paying close attention to the conversation.” Patrick, who joined them on occasion, tried to hide by parking two blocks away, but detectives were aware enough of his maneuvers to photograph him from a rented second-floor

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apartment across the street.7 He was willing to walk two blocks in the Chicago winter for a schvitz, but it didn’t keep him from prying eyes. The police did more than simply shadow Patrick. They shut down one after another of his street-level operations. By 1970 they’d made things difficult enough that Morris “Mushie” Lasky, a Patrick operative who ran what was described as “one of the last [high-stakes] floating poker games in the city,” had to go on the run. After an arrest at 3006 W. Pratt, in what Tribune reporter Bob Wiedrich reported was Patrick’s territory, Lasky determined things were simply too hot on the North Side and relocated to 8910 S. Jeffery Boulevard. When police arrested him there, they found a well-appointed bar including, in a detail that wonderfully shows the Jewish character of the operation, “chopped chicken livers on ice.” As Wiedrich reported, Lasky’s relocation to the South Side was a major violation of Syndicate protocol, moving him as it did to the territory of a different mob lieutenant.8 This was vivid evidence of the hard time that the law was giving Patrick on his home turf. In a similar set of raids a month earlier, Chicago police brought down a pair of Patrick-sponsored sports-betting wire rooms. Each featured equipment that permitted the gamblers to get near instantaneous racing results, making it possible for off-track wagering, a popular alternative for gamblers too busy for more than a quick phone call.9 The raid at 6221 N. Kedzie was notable not so much for the $6900 in cash or the loaded .25-caliber pistol that police recovered from Seymour Silverman as for the fact that Silverman unleashed his twenty-five-pound Siamese cat on the police. Though they were scratched up, the arresting officers permitted Silverman to releash “Poopsy” so they wouldn’t have to shoot him. The raid at 6723 N. Rogers went more smoothly. As the Tribune’s John O’Brien drily put it, “Julius Rosengard, 49, described as a henchman of Lenny Patrick, the crime syndicate’s North Side gambling boss, was arrested at the Rogers Avenue address. No animals were found there.”10 Such losses no doubt added up for Patrick, but what really must have worried him was the growing attack on his ability to protect his various gambling operations. It had long been an open secret that he had access to police protection, but it was suddenly unclear whether he could sustain it. At the same time as one part of the Chicago Police Department worked its own investigation parallel to the FBI’s, other officers continued accepting bribes and kickbacks to keep his operations going. While there were obvious reasons to hide most of those illegal relationships, Patrick, perhaps to assert that he was still the boss, flaunted some of his

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connections, going so far as to have a Chicago Police lieutenant chauffeur him in public. In addition, he let it be known that he sometimes asked police to wiretap his own bookies to catch them if they shortchanged him on the take.11 Patrick’s actual personal ability to influence political figures and, through them, the police, may have varied from year to year and precinct by precinct, but what really mattered was the perception that he had such influence. Letting people know about his ability to continue protecting his gambling centers—without quite giving evidence of the corruption—was part of the plan, part of what made him the boss.12 One shot at the arrangements that sustained him came when Chicago police raided the Backstage Lounge at 935 W. Wilson on March 10, 1973. While a bit south of Patrick’s reputed district, the head of the operation was identified as an ex-policeman who’d been kicked off the force in 1971 and since then had been known as a Patrick lieutenant. Arresting officers found a notebook that contained the numbers of nine Chicago police officers as well as “unlisted telephone numbers of several top figures in the crime syndicate.” Illegal as the operation was, it was so widely known that FBI agents turned out to be conducting simultaneous plans to break it up.13 There had been significant arrests at the place going back at least to 1966,14 and the Tribune’s Bob Wiedrich would call it “the Sodom of Uptown” a year later when it was still operating.15 The raid on such a “protected place” along with others like it demonstrated what had been Patrick’s power to get around the local police, but it showed the degree to which such standing was under siege. As one Tribune report from December 1973 put it, “Increasingly, federal agents are unearthing information indicating that as recently as 1971 close ties existed between certain ranking police officers, their subordinates, and a brace of gambling lieutenants of mobster Lenny Patrick.”16 But the biggest vise tightening on Patrick, the campaign most likely to incite his paranoia, came from the federal grand jury that had subpoenaed him to testify on his knowledge of organized crime. The investigation’s goal wasn’t so much to get Patrick himself. Instead, he’d been granted immunity in exchange for his knowledge of what higher-ups like Tony Accardo, Joey Aiuppa, and Gus Alex were doing. From one perspective, it promised a get-out-of-jail-free card. The information he revealed could not be used against him later, only against the others. If he talked about his own crimes, he’d make it almost impossible to be prosecuted for them. The price of such candor, though, was the end of his Outfit life. There was a way out, but Patrick didn’t want it. He was a mob boss, someone feared and, in his

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way, respected. He’d worked forty years to get and hold onto such a place. He had money and a license to swagger. He was right where he wanted to be. Patrick wasn’t the first domino in the government’s plan. Two of his associates, Eugene “Yudie” Lufman and Norman Rottenberg, reputed bookies who helped run the gambling operations of the North Side, had been caught in the same devil’s bargain a year before. Both refused to talk and were being held indefinitely on contempt. It had been a year, and both were still behind bars. Patrick found himself staring at his own dilemma. The rules were clear: stand-up guys did their time and didn’t talk, but the price of that was jail until the end of the decade. He no doubt felt he could let his underlings stew in prison, but it was a different matter to “snitch” on someone like Gus Alex. He knew what his choice meant: pay the price or get some of the Syndicate heavies to pay it. The year of 1974 was only just beginning, the Feds and the cops were everywhere, and he had a decision to make.

II If you set aside the murder, extortion, Syndicate ties, gambling interests, and impending grand jury testimony, the Lenny Patrick of 1974 had a lot in common with other Chicago Jews of his generation. Like them, he’d moved on from the Jewish West Side where the decline of the Jewish community that began around the end of World War II was largely complete.17 Some had dispersed to the suburbs or to comfortable neighborhoods like Hyde Park, South Shore, and the lakefront, but around 195218 he had followed the largest group, concentrated on the Far North Side in Rogers Park and West Ridge.19 There were still plenty of individual Jews in greater Lawndale on the West Side, but Jewish businesses and institutions—like the gambling concession Patrick and Zuckerman clashed over—were mostly gone, the result of changing demographics as well as, eventually, the riots that followed the assassination of Martin Luther King, Jr., in 1968.20 The Jewish gangster, like the rest, had left Lawndale for greener pastures. Patrick lived for most of the 1960s and early 1970s at 2820 W. Jarlath, at roughly the boundary between West Ridge and Rogers Park, in the heart of the most Jewish part of the city.21 At sixty-one he had a history of heart trouble22 but was still vigorous, still a strapping five feet, eleven inches, and 200 pounds.23 He remained a figure about town, patronizing one restaurant after another, and though not officially married, he lived with his common-law wife, Emilie Siben. He had plenty

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of money, some of it even legitimate from his ownership in a series of Little Big Dollar stores and his stake in the Herman Sales business on the South Side.24 For a time Gus Alex arranged for him to have a “ghost job” at Cosmopolitan Laundry, where he collected a salesman’s salary but had no actual responsibilities and rarely went into work.25 And, of course, he had his cut as the boss of gambling on the North Side.26 But 1974 marked a watershed in the world of gambling and corruption that had been so good to Patrick. That was the year that Illinois began its state lottery, undermining the profits that organized crime had taken for decades from its numbers racket and “policy” games. It was also the year the Supreme Court found unconstitutional the 10 percent tax on sports gambling—a tax that had made Las Vegas betting too expensive to compete with the illegal gambling that was Patrick’s tenderloin. The result was a slow-motion blow to the network of handbooks and independent bookies who took most of the local illegal bets. Legalized gambling boomed from small Vegas “turf clubs” to the casinos of the Strip and, within just two years, to national television with the weekly NFL Today commentary of oddsmaker Jimmy “The Greek” Snyder.27 Illegal sports action certainly didn’t dry up, but it had competition on the horizon. That same year also brought to a head pressures that, in many ways, resulted in the end of the Chicago machine as it had functioned since the early 1930s. The first Shakman decree of 1972 made it illegal for Chicago and Cook County governments to hire or fire personnel based on patronage. That system had been central to the way the longstanding Democratic machine functioned; someone who owed a job to an alderman or a municipal sanitary-district trustee could be counted on to mobilize an extended family of election volunteers every time the polls opened.28 In and of itself, the process didn’t feed into organized crime, but it did create opportunities that Patrick, as he testified later,29 exploited through payoffs to aldermen and fixers, who ensured the money would buy freedom of operation. In 1974 the first election took place after that substantial change, and if its effects weren’t immediately obvious, it marked one more alteration to the criminal ecosystem. What was obvious that year was a breakdown in the apparatus of the machine. In 1948 a Chicago Democratic committeeman could famously reject a would-be volunteer with the line, “We don’t want nobody nobody sent,”30 demonstrating the sense that backroom brokers made all the decisions that counted.31 Twentysix years later then-US Attorney and future Illinois governor James Thompson brought charges against a number of previously untouchable elected officials,

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convicting them of mail fraud, tax evasion, and conspiracy, and opening up the machine to democratic reforms that resulted, before long, in the elections of Jane Byrne and Harold Washington. Thompson’s biggest takedown was Thomas Keane, Mayor Richard J. Daley’s point-man and chief dispenser of patronage—in other words, the number two man in the pyramid. The stress of the prosecutions contributed to a stroke that kept Daley himself out of City Hall for months and left the political establishment on a shakier foundation than at any time in a generation.32 And of greatest consequence for Patrick and the Outfit as a whole, law enforcement officials were just beginning to realize the power of the Racketeer Influenced and Corrupt Organizations statutes from 1970’s Organized Crime Control Act. It was RICO that lowered the bar for convicting gangsters, making it possible to find them guilty for benefiting from a pattern of crimes even if they were not directly implicated in those crimes. Under some circumstances, then, it made it illegal for gangsters even to be seen with one another. RICO made it possible for the government to arrest Lufman and Rottenberg, offering them immunity in exchange for their full testimony. And RICO was hanging over Patrick’s head if he refused to accept his own immunity deal and testify against the big shots. Gus Alex was so concerned about the implications of the new statutes that he reportedly directed Patrick to dissolve his bookmaking operations in 1970.33 When Patrick revived them, he did so only carefully, having his bookies call customers to receive bets rather than leaving lines open to take whatever bets people wanted to place.34 Feeling the pinch from increased attention and decreased opportunity under the traditional rules, Patrick had to push into ever riskier areas to keep the money coming in. The good thing about overseeing gambling, even when everyone seemed to know you were doing it, was that it was relatively safe. Gamblers would come to you, to your handbooks and strolling bookies. They would give you their money, and more often than not, you’d get to keep it. Often, they’d lose enough that they had to borrow from you, and you’d supply it at usurious interest, what they called a “juice loan” in Chicago. Patrick’s operation was very lucrative, peaking at a take of $850,000 in 1969.35 As 1974 dawned, though, that approach got more and more difficult to sustain. The FBI and Chicago police campaigns hurt. He had to push the boundaries of what he’d been doing. He’d been an armed robber in his youth, and a murderer through much of his young manhood. He certainly had the stomach for the rough stuff. He was just a little rusty with it. Extortion is a pretty basic racket. You threaten someone until he, or possibly she, agrees to pay. It doesn’t take a lot of organization. It requires you to project an imposing-enough image to look as if you’ll follow through on your threat. And it

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requires that you select your victims strategically. If you try it on most law-abiding citizens, they go to the authorities. They insist on their rights and bring unwanted attention. The trick, then, is to find people who are already somehow compromised, people who have the kind of secrets that make them want to keep their business as far as possible from law enforcement agencies. One such person was Allen Dorfman. The stepson of Paul “Red” Dorfman, an early Teamster official and partner with Jimmy Hoffa in the rise of that union to national prominence, Allen Dorfman played a crucial role in the Chicago Syndicate’s move into Las Vegas gambling. As the insurance agent responsible for investing union pension funds, he supplied the loans that made it possible for Syndicate-connected figures to purchase casinos such as Caesars Palace, Aladdin, and Circus Circus.36 As a consequence, Chicago gangsters generally had a larger Vegas footprint than their New York counterparts, despite the notorious head start that Bugsy Siegel had given them. That arrangement became public when Allen Dorfman was convicted in 1972, but he still had plenty of secrets—enough that he’d be charged again at the end of 1974, would be the subject of a major FBI investigation in 1979, and would eventually be killed in a spectacular 1983 assassination after the fallout from the Las Vegas operations of Lefty Rosenthal and Tony Spilotro.37 Early in 1974, after claiming to get the go-ahead from Gus Alex, Patrick dispatched his lieutenant Lenny Yaras, son of his longtime partner, David Yaras, to demand a large sum from Dorfman. Yaras’s precise words are lost, but he was persuasive. The harried financier coughed up $300,000, not bad for just the asking, but even then Patrick found himself checked. Just as he demanded that weaker others pay him, he understood his obligation to pay tribute to the ones who made his own standing possible. As he explained later, he and Yaras kept only a quarter of the take, passing $225,000 onto their Syndicate bosses.38 Desperate as Patrick may have found himself, he knew better than to try to cross men who could easily have him killed. Patrick worked the trick on a handful of others around the same time. He approached the owners of the Black Angus restaurant at Touhy and Western, a place he was known to frequent,39 and demanded not just money but the opportunity to “put somebody in there”—meaning to create a sinecure or all-out ghost job for one of Patrick’s men. He wound up with $500–$600 a week for over six months. In the case of mob-connected bookie Yussie Meyers, Patrick simply walked up to him, showed a gun, and announced that he’d kill him if Meyers didn’t hand over some cash. That time he got $150,000. In each

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instance, Patrick reported, he made certain to take only his deserved cut and then pass the lion’s share upward to Alex and others.40 The most striking bit of extortion from the time, though, came when Patrick went after his own nephew. As Patrick told the story, he’d loaned his brother Mike $250,000 several years earlier. With times getting tough, he wanted the money back, but Mike was slow to pay, claiming he’d lost it all at the track. Patrick decided then to go after Mike’s son-in-law, pharmacist Shelley Miller, applying indirect pressure to his brother. He didn’t actually hurt his nephew, he took pains to make clear. “I jarred him up,” as he put it. “I had somebody shake him up. They didn’t kill him. He’s still living. He looks pretty good to me.” In any case, Mike repaid him the $250,000 almost immediately. While Patrick claimed to share $30,000 of the take with the crew that had helped him with the errand, in this instance he held onto the rest without paying off his Syndicate superiors. As he explained it, “[It was] my own money. I don’t know where I made it, but I had it and for years. And that was my own money. And that is the only way I got it back.”41 It wasn’t exactly an honorable way to make a living, but it paid the bills, and it forestalled the difficult choice about how to deal with the demand that he tell the grand jury what he knew or do his time in jail. As one Tribune piece put it, “Over this weekend, Patrick is undoubtedly wrestling with his underworld ethics. If he talks, he’ll be labeled a pooch and perhaps worse by his colleagues. However, if he doesn’t, Patrick will lose his freedom, his Cadillacs, and the soothing company of his peroxide blondes.”42 He was bringing in the money he needed to keep himself going, but he could play the naked-thug card only so many times. Gambling was essentially a victimless crime, but his strong-arm work left a trail of victims, and one of them was bound to bring him trouble before long. He could keep the wolf from his door for only so long, even if he was a kind of wolf himself.

III In some ways, what was at stake for Patrick was his very life. As an FBI report from the time put it, “Patrick is ill from fear.”43 To put it bluntly, he was getting old, and even a modest sentence would have had him behind bars until past conventional retirement age. He was sixty-one and still relatively healthy, but who knew how long he’d have left. If Benny Zuckerman’s generation—the Al Capones, the Dean O’Banions, and the Jack Guziks—rode Prohibition into the formation of the Syndicate, it was Patrick’s generation—the guys like Tony Accardo and Gus

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Alex who were ten to fifteen years younger—who refined it into the industry that was getting hit hard in 1974. The gangsters who made the headlines in the 1920s and 1930s were mostly young men, brazen kids who risked the little they had to accumulate more. As things consolidated from the late 1930s into the 1950s, it was their protégés and lieutenants who took over. After that, there wasn’t that much new blood. As Bob Wiedrich put it in the headline for the scathing story in a Tribune Sunday Magazine story about the aging of the Syndicate, “The Old Gray Mob, It Aint What It Used to Be.”44 It was a long list of mobsters who’d died of natural causes in recent years: Paul Ricca, regarded by consensus as Accardo’s equal at the top of the heap; Felix “Milwaukee Phil” Alderisio and Sam “Teets” Battaglia, both purportedly onetime bosses at the level of Giancana and Aiuppa; Ross Prio, longtime North Side boss alongside Patrick; Fiore “Fifi” Buccieri, supposedly Patrick’s peer as head of West Side gambling; and Murray “the Camel” Humphreys, the last of Gus Alex’s mentors in the business of corrupting elected officials.45 But the most personal such loss for Patrick must certainly have been David Yaras, who suffered a fatal heart attack in Miami on January 4, 1974, at age sixty-one.46 Yaras and Patrick had a long, shared history of murder and mob involvement They had been implicated in more than a half-dozen killings together, had formed the most notorious Jewish murder squad in Chicago history, and remained linked as partners from at least the day Benny Zuckerman was shot on his front yard. In fact, it was more likely Yaras than Patrick who pulled the trigger in that murder. They were such close friends that Yaras even named one of his sons Leonard and apparently gave his blessing as young Lenny apprenticed himself to Patrick’s crew. And each had long had the other’s back. Among other things, Patrick sustained the day-to-day oversight of street-level Chicago crime as Yaras largely relocated to Florida, and Yaras, in the words of Wiedrich, “furnished the brains for the lucrative Patrick sports and horse betting network on Chicago’s North Side.”47 Yaras was dead, and Patrick had to worry that another old friend might turn on him. Eugene Lufman, widely described as his top lieutenant in gambling operations, was one of the bookies held on contempt charges for refusing to testify against him. Lufman, like Patrick, went back almost all the way to Prohibition. He had a conviction for avoiding alcohol taxes in 1936, and he’d been routinely picked up for gambling throughout the 1950s and ’60s.48 He was, in fact, a couple years older than Patrick, and the two had feuded in 1973, culminating in Patrick’s hitting Lufman over the head in front of witnesses.49 Lufman did his time without talking, though; he stayed in jail for the full seventeen months the grand jury was

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empaneled. One newspaper report claimed he’d offered to bribe his jailers with an all-expenses-paid gambling junket to Las Vegas,50 but he stood his ground in all the ways that were important to the likes of Tony Accardo and Gus Alex. Patrick finally gave in to the pressure and talked, but he mixed a large part of invention with the little truth he told. He admitted he’d paid $500 a month to Lieutenant Ronald O’Hara, his erstwhile chauffeur and bagman for the Fillmore police district.51 He claimed he’d quit the gambling business in 1971, after RICO came in, but he said nothing about reports that he’d found ways to continue with a diminished profile. He denied he’d had anything to do with the Black Angus restaurant. He insisted he knew nothing about the murder of North Side bookie Boodie Cowan when, in fact, he knew his brother Mike was behind it and may have had a hand in it himself. To put it simply, he danced around the truth. Years later, he would admit to mixing truth with falsehood in the story he told. When he was on the witness stand, an attorney asked him, “At that time, 1974, the oath didn’t mean anything to you, did it?” “Well, I lied,” he admitted. “It probably didn’t.”52 Just as quickly as he began talking, though, Patrick clammed up again. Some of it may have been reversion to the code he’d followed all his life—never talk to the cops—and some of it was simply the pressure he felt from the only world he knew. On the quiet side, that came about when his old friends shunned him. An FBI report from early 1975, for instance, described him as a “recluse” and a “sorry case” and reported that, when he attended the funeral for the widow of longtime Syndicate boss Paul Ricca, “everyone avoided him.”53 On the more forceful side, it meant a visit at his home from O’Hara, acknowledged as someone “with a reputation for violence and murder.”54 The case against O’Hara rested on Patrick’s testimony so, when he refused to speak in open court, it meant O’Hara was acquitted.55 Patrick had seen what it was like to testify against the Syndicate, and he didn’t like it. The grand jury had him from all directions, so he decided he’d go ahead and take his medicine. Patrick’s nightmare of 1974 ended in his conviction the following year when he got a four-year sentence at Lexington Penitentiary.56 He missed most of the rest of the 1970s, but he kept his head down and trusted the organized-crime system that had gotten him where he was. He’d been a boss ever since Benny Zuckerman’s murder, and he accepted the promise that he’d remain one when he got out. There would be plenty of opportunities waiting for him, some legit, some the continuation of crimes he’d long been involved with, and some new crimes altogether. With luck, he’d live another twenty years, possibly even more. Above

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all, he’d proven himself a stand-up guy. He’d shown the higher-ups they could count on Lenny Patrick to keep his mouth shut. In part because of his criminal contempt, the Feds’ hopes to shut down the Outfit failed that year. They would try again eighteen years later, though, and Patrick would have another tough choice about whether to turn on the Syndicate bosses who had made possible his control of Jewish organized crime for almost two generations.

4 LANDING IN LAWNDALE

I Davey Miller was a fighter. He once boasted to a national magazine that while he never carried a gun, “I could always lick any five boys or men in a sidewalk free-for-all.”1 Born in Cincinnati,2 likely in 1890,3 he moved to Chicago as a young child. He grew up in crowded Maxwell Street as one of nine children4 in a family so poor that, at least according to family legend, they had to place him and some of his brothers in the Marks Nathan orphanage.5 As a teenager, he became a good-enough boxer that he was selected as Chicago’s heavyweight representative in the national amateur championships of 1914,6 and when he stopped fighting in the ring himself, he went on to become arguably Chicago’s most distinguished referee.7 He helped establish the Golden Gloves amateur boxing tournament8 and mentored dozens of fighters, most famously future multiple-world-champion boxer Barney Ross.9 By the end of his career, he was a widely recognized elder statesman for the sport, a figure celebrated by, among others, Damon Runyon,10 and an honoree of Chicago’s Jewish Sports Hall of Fame.11 Miller was an operator, too, someone who, barely into his twenties, managed to get a foothold into legitimate businesses that let him oversee gambling and other elements of organized crime. He opened his own restaurant in the Maxwell Street area at 1639 S. Taylor Street12 as early as 1912,13 and he moved to what would become his landmark Lawndale restaurant, gym, and gambling center by at least 1915.14 He was part of a web of legitimate businesses—including restaurants owned by his brother Hirschie15 and his brother-in-law Harry Block16—as well as illegitimate ones: originally the gambling that took place in and around the restaurants and later the bootlegging that became possible with the advent of Prohibition.

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And from the beginning he managed to secure himself the political connections it took to keep from getting arrested and harassed. As far back as 1913, 20th Ward Alderman Manny Abrahams claimed him as a friend—in the wake of Miller’s having been in a fight with two policemen, no less17—and Abrahams’s eventual successor, Morris Eller, reportedly sold him protection throughout the early years of Prohibition.18 By 1925 sociologist Frederic Thrasher would acknowledge the gang he led as one of the “master gangs” of the city.19 Miller was best known, though, for being a “Samson”20 or “Judah Maccabee of the West Side.”21 He appointed himself protector of the everyday Jews who encountered violence as they moved from Maxwell Street to other parts of the city. Stories place him almost everywhere Chicago Jews found themselves threatened. Sometime around 1913, on the Near West Side “in the alleys around Hastings and Laflin,” just beyond the major Jewish presence around Maxwell Street, Miller organized a gang to beat up a group of toughs who’d attacked Jewish peddlers.22 During Passover in 1915, in the South Shore neighborhood, he intervened in a blood libel circulating among the Poles of the St. Michael’s Church parish, negotiating with the priest to point out that no Polish children were missing and that the newcomer Jews could not possibly have killed a child to make matzo.23 In the early 1920s in Uptown, he organized a gang to fight young gentiles who were harassing Jews who tried to use the North Side’s Clarendon Beach.24 And in 1921, in the Humboldt Park neighborhood on the near Northwest Side, he and another gang helped nine-year-old Albert Epstein and several of his Jewish friends who’d been bullied on their way to school by Irish, Polish, and Swedish toughs. The older boys would pretend to come to the “rescue” of their own younger friends, whom they’d goaded into confronting the Jewish boys, and then overwhelm them “at least five to one.” As Epstein recalled, “Unknown to me, Davey Miller was called. He and his boys were shadowing us as we walked to school. As soon as they saw we were about to be attacked, they jumped out of their cars, seized the bullies, and roughed them up. From that day on, the Jewish boys walked to school in peace.”25 As available as he was across the city, Miller’s clear focus was Jewish Lawndale. From the time he established his M&E26 restaurant and gym at 3216 W. Roosevelt Road, it became a center of Jewish self-protection as the neighborhood rapidly transformed into the largest and most concentrated community in Chicago Jewish history, one that by the middle 1930s reached a population of 110,000 and encompassed roughly 40 percent of Chicago’s Jewry.27 Jews had begun to establish a presence in the particular neighborhood of North Lawndale as early as the end of the first decade of the twentieth century,28 and from there they began to move

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into neighboring Douglas Park and East and West Garfield Park, establishing the Jewish community of greater Lawndale or, as most Jews referred to it, “Lawndale,”29 complete with distinctly Jewish communal, cultural, and business institutions. Still, while the Jews moving to greater Lawndale in the late 1910s and early 1920s looked like “Yankees” to some of the more Orthodox Jews they left behind on Maxwell Street,30 they appeared as unwelcome foreigners to many of the existing residents. Some of the German and Irish landlords of North Lawndale refused to rent to them,31 youth gangs often harassed or attacked them, and there were even rumors of pogroms put together by angry Polish neighbors who worried that Jews would displace them from Douglas or Garfield Parks.32 They had the legal right to make a new home, but they often needed help from the other side of the law to enforce that right. And Miller, with his shtarkers—Jewish toughs and would-be gangsters like his brothers, the young Benny Zuckerman, and family members of the even younger Lenny Patrick—provided that help. At times, Miller supplied his assistance almost like a public service. Harry Shoub lived with his family in an apartment across from Douglas Park, a regular site of conflict between Jews and aggressive neighbors. As he remembered it, “Miller’s restaurant was two blocks west of where I lived, so when a call of distress was phoned to the restaurant, Miller picked up the phone, called out to the fellows, and they ran to their cars like firemen rushing to a fire.”33 Sam Simon recalled the same phenomenon. “Our biggest problem came in Douglas Park. Jews lived west of the park; goyim lived east and south of the park. . . . There was an indoor swimming pool in the park. Swimmers had to go in naked. So the goyim used to look around for the circumcised guys. Man, we had trouble. Finally they run us out. We couldn’t even go to the pool,” he said. “We told Davey Miller it was impossible for Jewish kids to play in the park. One day as we were playing ball, Davey Miller came out there with the guys from the restaurant and gym. They came in automobiles right on the football field, and they started cracking skulls. It never happened before. Those guys who were ganging up on us thought they could beat us up and get away with anything. It must have been a real awakening for them. Then things eased up for us.”34 In the early years, those street conflicts could look a lot like full-on battles. Leon Sex, whose family moved to North Lawndale in 1913 as part of the earliest wave of migration, recalled that there was a particularly aggressive group of Poles who lived just west of Pulaski Road. “Young punks—they were anywhere from fifteen to twenty-five years old—formed bands of forty, fifty, and sixty guys, and they would come down Roosevelt Road, looking like they owned the street, looking

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for Jewish kids to gang up on,” he said. “It was Davey Miller and his boys that met up with the Polish invaders, and they knocked hell out of them. Roosevelt Road wasn’t Poland, and Jews didn’t have to hide. The Polish guys quickly became reeducated; they never came back.”35 The Jewish Daily Courier reported the showdown stopped just short of becoming a full fight, crediting “Jewish boys who frequent the lunchrooms of Davie Miller, Pudi Anikster” and other reputed gambling centers with presenting a show of force that was “enough to frighten even a greater number of Poles than we have in Chicago.”36 Sociologist Frederic Thrasher put it more soberly, recounting that Davey Miller and his gang, “are alleged to have successfully stemmed an invasion of Lawndale from the southeast by Polish gangs intent on following the example of their kinsmen across the seas and holding a pogrom in the Jewish residential area.”37 Miller himself recollected a similar experience that coincided with the end of World War I, telling Collier’s magazine, “Why, during the Peace Conference at the very same time that the Poles were trying to get the statesmen to let all the Jews out of Poland, there were 10,000 Jews here at the restaurant on Sunday afternoon yelling for me to come out and lead them over into the Polish district. The Chicago Poles had made the threat they were going to come into the Ghetto and have a pogrom against us. Maybe I am a hero to the young folks among my people, but it’s not because I’m a gangster. It’s because I’ve always been ready to help all or any of them in a pinch.”38 From one viewpoint, then, Miller’s role in helping win the streets for law-abiding Jews demonstrated the degree to which crime was part of the foundation of Jewish Lawndale. Miller’s generosity in helping Jews in danger wasn’t merely altruistic; it gave him a standing in the community that helped make possible the gambling and, later, booze operations that supplied him with real wealth. Who, after all, would “rat” on the guy who’d rescued you or your family? In similar fashion, it helped make him valuable to politicians who drew on his financial and popular support, and it’s no coincidence that the 24th Ward office was located only a few storefronts away from his restaurant.39 Other neighborhoods saw a similar fusion of crime, community and politics; in the 12th Ward of nearby South Lawndale, for instance, Bohemian saloon keeper Anton Cermak was already weaving his connections to street toughs, electoral politics, and a defined ethnic community as he put together the organization that eventually produced the famous Chicago Democratic machine.40 But Lawndale had a particular renown for the way in which communal life meant being aware of the power of organized crime and electoral politics. A 1914 report from the Yiddish-language Jewish Courier

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complained that, in place of libraries, Lawndale had only pool rooms, saloons, and gambling dens, leading to the conclusion that “there is not in Chicago a Jewish district so spiritually impoverished as the one that extends from Douglas Park to Independence Blvd.”41 Or as sociologist Beryl Satter put it as she reflected on her father’s experience in the neighborhood, “Growing up in Lawndale, children learned the word gang as soon as they learned to talk.”42 Within that community, Miller held a particular and romanticized standing. He wasn’t quite the first of the pioneer gangsters in the neighborhood—Julius “Lovin’ Putty” Anixter preceded and outlasted him. He also wasn’t the most successful— again that was Anixter and Anixter’s eventual protégé, Benny Zuckerman; Miller bet the wrong way when he threw his political allegiance to the Republican apparatus of Big Bill Thompson and Morris Eller, since the Democratic machine of Cermak and Jacob Arvey proved more consequential in the long run. He was, however, Jewish Chicago’s highest-profile figure in the citywide gangster confederation that emerged in the early years of Prohibition, and he was the smiling criminal face of the gangs that first emerged in Jewish Lawndale. To a rising generation, he represented the possibility of Jews defending themselves as Americans in their new home. And, to many of the old-timers who spoke of their childhood, he became a symbol of Jewish Lawndale when it was just emerging as an unprecedented “Chicago Jerusalem.”43 He was entwined in the emergence of the West Side as a Jewish community, someone remembered with unusual fondness for a figure of organized crime, someone central in the process that allowed Jews to land, for a generation, in Lawndale.

II Davey Miller, like Jewish Lawndale itself, was full of apparent contradictions. The neighborhood boasted sixty-five synagogues or other places of worship.44 At the same time, it featured such a thriving underworld that a single raid on November 20, 1921, brought in seventy-three gamblers from at least five different illegal gambling dens.45 Miller himself was both a substantial businessman in the burgeoning community and a recognized criminal. One newspaper article of the time got at that contradiction by putting quotation marks around “restaurant” in a story reporting the gambling that took place there, using the punctuation marks to underscore the quasi-legal standing of the place.46 Similarly, in 1933 Collier’s magazine sent a reporter to interview Miller for his insights on the allure of

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gangsterdom for the boys of his world. Reporter William G. Shepherd talked of “sitting in his splendid restaurant in the Ghetto,” as Miller denied being a gangster but admitted that his brother Hirschie probably was.47 The tone was cheerful, but the implication was clear: no one came to own a restaurant like Miller’s in a place as gang-ridden as greater Lawndale without being somehow in bed with serious criminals. Miller did what he could to straddle the legitimate and criminal worlds, particularly in his work as a boxing referee,48 but he couldn’t always walk the tightrope. He refereed at the highest levels of the sport, overseeing fights across the United States that included such eventual world champions as James Braddock,49 Primo Carnera,50 Jake Lamotta,51 Benny Leonard,52 and Joe Louis.53 In what was in some ways the culmination of his career, he refereed his only heavyweight title fight on June 22, 1949, at Comiskey Park when Ezzard Charles defeated Jersey Joe Walcott,54 but that was only consolation for the even greater opportunity that got away. When the September 22, 1927, heavyweight-title fight rematch between Jack Dempsey and Gene Tunney was first scheduled for Soldier Field, Miller was announced as the referee. He was replaced at the last minute, though, by Dave Barry who, in what became known as the “long count,” was slow to begin the knockout countdown after Dempsey dropped Tunney to the canvas. The result was that the underdog Tunney eventually rose and went on to win one of the most storied matches in history in front of the largest crowd ever to witness a prizefight.55 As sportswriter Paul Gallico summed it up a decade later, “Davey Miller was the number-one referee around Chicago in those days. But Davey was Capone’s man, and too blatantly so. The situation outraged the Chicago Boxing Commission sufficiently to give it courage to buck Capone, keep Miller out of the ring, and substitute Barry, with the results that are history. Miller would have counted Tunney out.”56 Gallico probably oversimplified both the implications of the referee change and Miller’s connections to Capone—in fact, Miller later claimed he’d been replaced as referee precisely because he refused a bribe from Capone57—but his central point was on target. No matter how successful Miller became, he could not always avoid the stigma of his ties to organized crime.58 A substantial part of Miller’s slippery position with the law came from the public fact that others in his family were prominent lawbreakers as well. As early as 1921, a Daily News article referred to the Millers as “four brothers who’d been active for the Thompson-Lundin organization in the old 20th Ward,”59 which was a euphemism for the claim that they’d been involved in election violence in the service of Morris Eller, the Jewish ward leader allied with Mayor Big Bill

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Thompson.60 In 1929, in the most comprehensive contemporary survey of that decade’s gangster figures, John Landesco referred to “the notorious Miller brothers, famous in vice, gambling, booze, politics, and gang warfare in the Ghetto.”61 One brother, Al, was named in 1927 as a front for smuggling Canadian liquor into the United States,62 suggesting the likelihood that he was involved in other ways as well. Max, the youngest brother, was labeled a partner in a similar importing scheme in 1924,63 and newspaper stories occasionally reported him as a gambling overseer.64 Most prominently, Max was tried for the murder of Abe Rubin on April 9, 1922, alongside boxer Sailor Friedman, who was scheduled to challenge for the lightweight title later that year. Max’s version of the events was that Charles “Chick” Hadesman had harassed Friedman’s sister, and the two had joined with three others to pay him back at Max Eisen’s saloon where Rubin was hit in the crossfire.65 Prosecutors claimed the real cause was a bootleggers’ war,66 while a confidential investigator for the Chicago Crime Commission speculated that the actual motive grew out of Hadesman trying to move in on the Miller brothers’ gambling operations.67 In any event, Max Miller was found not guilty; Friedman was convicted, but a subsequent retrial ended with a judge ordering the charges be dropped,68 meaning no one was held responsible for the killing. Miller’s brother Harry eventually had a higher profile than Max or Al. It may seem counterintuitive in a family of gangsters, but Harry became a decorated sergeant with the Chicago Police Department. While he was cited for bravery in the line of duty and seems at times genuinely to have risked himself in defense of law-abiding citizens, he also used his position to help himself and his family. In one dramatic incident on January 24, 1919, barely a year into his time on the force, he scaled a fire escape and shot it out on the roof as he tracked down and killed a thief. He got a flattering photo in the paper,69 and the city awarded him a Distinguished Service Cross for his heroism.70 In what was either an extraordinary coincidence or evidence of the deeper nature of Harry’s police work, however, the victim of that robbery was Manny Goodman, an illegal saloon keeper himself and a onetime political figure from the 20th Ward for whom the Miller brothers had earlier campaigned.71 Over the course of roughly fifteen years, Harry had an up-and-down career with the department. He was kicked off the force in 1921, in part because of his connections to his brothers,72 but then apparently reinstated soon after. He was suspended again in 1925 when he and Davey were caught in a government sting operation as they extorted payoffs from opium peddlers,73 but again he returned to the force. By 1933, as historical novelist Max Allan Collins saw it, Harry was

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one of the detectives “handpicked by Mayor Cermak to handle the dirty linen,”74 which meant, among other things, that he had a hand in accepting illegal payoffs from criminals destined for political corruption. In that capacity, Cermak placed Harry in charge of his “Hoodlum Squad,” a police strike force aimed at breaking the power of the Syndicate in the years after Capone had been sent to jail. Harry and his partner Harry Lang went so far as to attempt to kill Syndicate boss Frank Nitti. When they botched the effort, it marked the end of Harry’s police career at last, and at least according to some conspiracy theorists, it precipitated the Syndicate’s assassination of Cermak as he rode in a car alongside newly elected President Franklin D. Roosevelt.75 After Davey, though, the highest-profile Miller brother was certainly Hirschie. Roughly a year younger than Davey, Hirschie attempted the same balance between legal and illegal activities, appearing as a boxer himself,76 trying to join the police force in 1921,77 and managing to serve as bailiff to Municipal Court Judge John Caverly.78 He tried at least twice to open a restaurant comparable to the M&E,79 but he never succeeded over the long term. Instead, he was drawn almost immediately into the opportunities that Prohibition offered. According to historian Robert Schoenberg, Hirschie committed the nation’s first substantial violation of the Eighteenth Amendment when he oversaw the hijacking of a truckload of whiskey several hours before it went into effect.80 In short order, he established himself as an early bootleg kingpin and affected a swagger with his newfound wealth. Hirschie crashed into newspaper headlines alongside Samuel “Nails” Morton when he shot and killed two off-duty policemen on August 23, 1920, at the African American–owned Pekin Inn at the Beaux Arts Café.81 That night Morton, who would go on to establish the North Side Gang along with Dean O’Banion, was reportedly carrying as much as $60,000 in gambling winnings,82 and Hirschie, described in one newspaper account as “now living an ‘easy life’ on his income,”83 had a substantial bankroll as well. Different accounts varied, but most described officers William “Spike” Hennesy and James “Pluck” Mulcahy as indicating they expected a payoff. Morton resisted, the officers knocked him to the floor and went for their guns, and Hirschie fired in what he called self-defense. The scandal went beyond the fact that the victims were policemen to the way it revealed a larger web of police and political payoffs. City ordinances required all such clubs to shut down at 1 a.m.—the shooting took place around 2 a.m.—so it was evident the police were themselves there illegally, likely in search of bribes.

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The subsequent investigation revealed what the Tribune called “stories of graft in the Maxwell Street police district; of gambling unrivaled in recent years and flourishing undisturbed, and of a combination of police, politicians and whisky thieves formed for the disposal of hundreds of thousands of dollars’ worth of moonshine.”84 It also revealed the extent of the political and financial power of the Miller brothers. Before the start of business the next day, Alderman Joseph Kostner was already huddling with Davey Miller,85 and he was soon joined by former alderman and chief Municipal Court bailiff Dennis Egan86 and Mayor Thompson’s secretary, Charles Fitzmorris.87 The trial dragged on more than a year and a half, and newspapers reported several claims of witnesses who were bribed to tell a favorable story about Hirschie or simply to disappear.88 There was even worry that Hirschie’s confederates might break him out of jail.89 In the end, he was found not guilty of Mulcahy’s murder on October 1, 1921,90 and of Hennesy’s on January 7, 1922.91 It had taken considerable clout and, in the estimate of an anonymous Crime Commission investigator, $100,000 of Davey’s money.92 But the brothers pulled it off, and Hirschie and Morton both walked free. Emboldened, Hirschie began venturing into racketeering, the other major branch of criminal activity in the era. In order to compete with similar operations overseen by Syndicate and north-side gangsters, he formed a “protective association” for cleaners and dyers; the independent businesses he signed up— sometimes by friendly persuasion and sometimes unfriendly—agreed to charge customers a minimum price per garment. They kept a portion of that increase and then paid Hirschie a percentage so he could ensure other businesses didn’t try to offer lower prices. Everyone involved made a profit at the expense of the everyday consumer. Hirschie was on his way to a small fortune, but it put him in serious danger from rivals who had the same idea. On March 13, 1924, as he was driving through the intersection of Addison and Racine, a quarter mile from Wrigley Field,93 a car with five gunmen pulled alongside him and began firing. The conflict foreshadowed a scene from Ben Hecht’s Scarface with Hirschie trying to keep driving as bullets flew around him. He survived, but the attacks persisted. His association’s plant was bombed the next day, and multiple people called him with death threats.94 He and his brothers had enough clout to get him a cohort of police bodyguards,95 and the Tribune sent a reporter to sit with him, his wife, and mother-in-law as he weathered the strain,96 but it was clear he was outnumbered and outgunned. Bowing to the pressure that came from being an independent gangster trying to take on the larger confederation of the Syndicate and the North

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Side, he agreed to sell his ownership stake on August 15, 1924. He managed to secure a $150,000 profit after he sold his Acme cleaning plant for a quarter of a million dollars.97 He’d taken his shot at joining the gangster elite, and he was lucky to walk away alive.

III If Hirschie was the Miller brothers’ designated “Scarface,” Davey Miller did what he could to steer the family into the ever-growing confederation of the era. Jules Portugese failed in large measure because he couldn’t move beyond the narrow confines of Maxwell Street, and Miller’s early move to North Lawndale proved the opposite. He rose in power, at least in the early years, alongside the community he protected and helped establish. He became, for a time, one of Jewish Lawndale’s fixtures in the citywide constellation of organized crime, buying protection—and sharing it out for a price—from the centralized system of graft that orbited Mayor Big Bill Thompson. Miller’s go-between was generally 20th Ward alderman Morris Eller, who oversaw his own gang of toughs in the greater Maxwell Street area, but the larger system was really a web linking all the city’s successful gangsters. It was, in other words, what it meant to be “connected,” to be part of the confederation that Johnny Torrio had first put together when he saw the vast potential profits of Prohibition. It was the dimension in which someone like Paul Gallico could regard Miller as somehow “Capone’s man.” It’s hard to measure political clout since it expresses itself mostly by keeping the powerful out of the limelight, but one incident from 1919 shows that Miller had established his standing by the dawn of Prohibition. On December 21, police from the nearby Fillmore District station rounded up several of Lawndale’s most prominent gambling figures, including Miller and Putty Anixter. Anixter insisted the raids were evidence not of a new police crackdown but rather the result of another gambler, Louis Rosenberg, outbidding them for protection from the neighborhood patrolmen. Sensing the same double-cross, Miller “was seen to glance malignantly” at the three plainclothes officers who’d brought him in. “‘Get the first names of those three bulls,’ he said to one of his henchmen. ‘They’ll all be walking around in Hegewisch before long.’”98 It’s impossible to know whether the officers wound up on the city’s far South Side, but Rosenberg disappeared from the record soon after, while Miller and Anixter kept on without serious interruption.

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For a time in the early 1920s, Miller was, in a mid-sized way, big-time. That is, partnering with his brothers, he had interests in booze, gambling, and racketeering. Like Capone, who notoriously opened soup kitchens to improve public perception of him,99 he reportedly kept reporters from the two Hearst newspapers, the Herald-Examiner and the American, on his payroll to manipulate newspaper coverage of him.100 He was wealthy, certainly by the standards of a childhood that had seen him sent to an orphanage, and he controlled his territory well enough that, at least according to some contemporary accounts, his rivals on the North Side hired an out-of-town hitman to try to kill him.101 At the same time, that territory was circumscribed. For all that he’d made himself available to Jews across the city, his criminal footprint was limited to the greater Lawndale area. As a Chicago Crime Commission investigator observed, “Davey Miller’s ‘pool’ can’t operate outside of the Douglas Park district.” In contrast, the investigator asserted, the “Humboldt Park Yids”—North Side Jewish gangsters, including Max Eisen in whose saloon Max Miller and Sailor Friedman killed Abe Rubin and wounded Chick Hadesman—“can run anything they please all over town.”102 Still, Douglas Park, at the heart of Jewish Lawndale, contained a lot of Jews, most of them loyal to the man who’d protected them and their neighbors from the young toughs who had harassed them. Then, on January 20, 1924, North Side Gang boss Dean O’Banion, at that time a higher-profile gangster than even Capone, went up to Miller and his brother Max as they walked out of the LaSalle Theater in the heart of the Loop, placed revolvers against their bellies, and fired. Max’s belt buckle deflected the bullet, leaving him unhurt, but Miller was shot through the stomach and seemed, for a time, likely to die.103 The next few days were chaos as Miller slowly recovered and the city’s newspapers tried to make sense of what the shooting meant. The Herald-Examiner ran a banner headline across page one, screaming, “Gang War Over Miller Feared,” and various other papers speculated whether the shooting sprang from a controversial decision Miller had made as a referee,104 from lingering tensions over Max Miller and Sailor Friedman’s attempted murder of Chick Hadesman in Humboldt Park,105 from a feud with Putty Anixter,106 from O’Banion’s concern that Miller was trying to muscle him out of some gambling operations,107 or from O’Banion’s trying to take over Maxie’s wholesale bootlegging operation.108 The likeliest explanation, however, is a familiar one. Just as the Syndicate would one day replace Benny Zuckerman with the more loyal Lenny Patrick, O’Banion seems to have tried to replace the largely independent Miller with a loyalist of

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his own. When O’Banion shot the Miller brothers, he was accompanied by his usual sidekick, Hymie Weiss, but also by a relative newcomer to Chicago, Yankee Schwartz, described by the Herald-Examiner as a “second rate prizefighter, bootlegger deluxe and erstwhile hanger-on of Miller.”109 According to multiple reports, the shooting began after O’Banion asked Miller why he no longer seemed to trust Schwartz, and he replied “He’s no good.” And it was Schwartz, the HeraldExaminer went on, whom “Miller’s friends” blamed more even than O’Banion for the attempted murder. O’Banion had already established a reputation as a hothead, someone willing to shoot first and dodge questions later. As boss of the second-largest gang in the confederation Johnny Torrio had pulled together in the early 1920s, O’Banion had access to wealth and power far beyond what he could have imagined before Prohibition when he was a small-time safecracker and newspaper slugger.110 Still, despite being a millionaire, he chafed as a defined part of the Torrio-Capone confederation. He wanted it all, or at least more, and his shooting of Miller was an early salvo in what would become his all-out war with his erstwhile partners, one of his first moves to widen his assigned slice of the pie. His murder on November 10, 1924, precipitated the infamous gang wars that climaxed in the St. Valentine’s Day Massacre. Capone, as Torrio’s top lieutenant, reportedly tried to restore peace by passing along $5,000 from O’Banion to the Miller brothers. Miller told Collier’s he’d put it all behind him. “Excuse it, please!” he said dismissively. “Getting the wrong man with a gun is like getting the wrong telephone number.”111 Still, even though the Miller brothers survived the shooting—and survived O’Banion and his gang as well—their wings were clipped. Their most important political patron, Republican Morris Eller, took a tumble in his re-election, and they watched a new generation of politicians headed by Jacob Arvey rise to the top of Lawndale’s 24th Ward as the Democratic machine began its near-century-long grip on power. The booze market continued to mature, driving out all but the biggest players, and the Millers weren’t quite big enough to make the cut. By the late 1920s, Hirschie owned a small bar at 127 S. Kedzie on the northern edge of greater Lawndale, but his family’s diminished status was clear from the way he was subject to a series of nuisance raids that a truly connected gangster would never have had to suffer.112 He even endured the ultimate indignity when, in 1929, he was sentenced to three months in jail and fined $500 for selling illegal booze. When he died of natural causes—to the astonishment of all—on July 13, 1939, he owned a tavern in the Loop, one that barely recalled the splendor of his Prohibition success in Lawndale.113

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Davey remained a high-profile figure through his work as a referee, and through the rising generation whom he’d inspired in his efforts to fight anti-Semitic violence across the city. Young men as varied as future Judge Abraham Lincoln Marovitz,114 multiple world boxing champion and war hero Barney Ross,115 and Lee-Harvey-Oswald-assassin Jack Ruby, all expressed pride for the way he’d toughened them in a Jewish setting.116 Still, he too found his old clout fading. One report from 1928 even mocked him for striking out at City Hall where it claimed, “He spent the day here and there, weeping on various shoulders over being ‘persecuted’ by police and press.”117 He held onto the M&E restaurant and gym with its gambling concession upstairs until the middle 1930s and opened a new restaurant at 2600 Milwaukee, where he continued, in his own person, to be part of the attraction of the place.118 When he finally turned over the keys to his old place, the one that sat in the heart of the Jewish Lawndale he’d helped establish, he gave them to Ben Glazier and to a rising thug named Benny Zuckerman.

IV Davey Miller was the flashy underworld character, the one who made the headlines, but Julius “Lovin’ Putty” Anixter had the real staying power. Miller found ways to tap into the developing network of Lawndale political corruption, but Anixter was one of the architects of that network. Miller ran gambling and booze in his limited, defined part of Lawndale while Anixter ran things district-wide. Through his connections to other west-side powerhouses, including William Skidmore and Bill Johnson, he boasted connections that, while anchored in Jewish Lawndale, went beyond its borders. Where Miller knocked on the door of the Syndicate’s citywide confederation, Anixter opened it wide and established connections that would not merely last him the rest of his life but would lay the foundation for the independent Jewish operation that endured until Lenny Patrick brought it under direct Syndicate control with the murder of Benny Zuckerman. Low key as he set out to be, Anixter is perhaps best remembered for his unusual nickname. He supposedly earned it from his capacity to walk out of a private conversation with the deal he wanted. He was notorious for manipulating police and other officials, for treating them like putty in his hands.119 As recently as the 1980s, old-timers with firsthand memories of him made sure to pronounce it “poody” in almost the same way that Tweety, the little yellow bird from the Looney Tunes cartoons, would describe Sylvester as the “putty tat” stalking him.120

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The pronunciation was so striking that a 1933 United Press story, presumably written by an out-of-town reporter encountering it for the first time, transcribed it as “Love and Puddy.”121 Similarly, a recent transliteration from a 1919 Yiddish news story spelled it as “Pudi.”122 Like Miller and most of the other early Lawndale Jews, Anixter had roots on Maxwell Street. Unlike Miller who was barely out of his adolescence when he set out to make his mark in Lawndale, Anixter came to the new neighborhood with an accomplished résumé as a gambling operator. He was already twenty-eight years old when in late 1913 he purchased what would become his restaurant at 3607 W. Roosevelt,123 half a mile further west than Miller’s, and he did so as part of a long game. Lawndale was nowhere near the Jewish center it would be just a few years later, so he continued to operate his original club at 1343 S. Kedzie as well. There was time to cash in later. The public got a rare glimpse of the nature of Anixter’s political connections in 1917, when it came out that even the chief of police had to tread carefully around him. State investigators identified Tom Costello as the head of a major gambling ring that had arranged for protection directly from Police Chief Charles Healy. In an early instance of wiretapping, they recorded more than a hundred of Costello’s conversations and in open court pressed him to interpret what he’d said. After specifying he saw 1343 Kedzie as a rival, Costello reported that he and the chief had hoped to shut Anixter down, but they were “afraid to mix in” because Anixter had the backing of one of Mayor Thompson’s chief lieutenants, former Superintendent of Streets August Miller.124 If evidence of that clout weren’t impressive enough, Anixter’s name didn’t even make that particular testimony. He was invisible unless you happened to know he owned the Kedzie location. Anixter had a gift for keeping out of the limelight. In fact, many of the reports of him that survive from the late 1910s and early 1920s come from people frustrated with their inability to get anyone to pay attention to his crimes. The Day Book newspaper reported in 1917 the unusual story that Lena Barr, presumably unable to interest police in her plight, was suing Anixter to recover money that her husband George “lost in dice games.”125 Similarly, the Tribune ran a letter from a “Suffering Wife and Mother,” complaining that her husband “gambles away all the weekly pay and does not provide for me and our three children.” The woman made clear she was talking about Anixter. “The police of this district [Fillmore] know about this place. I have seen Putty handing money to a sergeant in front of the place; I suppose paying him for not interfering with his gambling.”126

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The most detailed such letter came in 1919 from a returning World War I veteran, Harry G. Green.127 He complained that he’d lost $1700 playing craps at Anixter’s Kedzie location in 1917 only to learn later that he’d been given loaded dice. He claimed Anixter had a long history of graft, including an unreported hand in a 1914 scandal where various politically connected figures bought real estate soon before the school board bid on it, giving them huge profits without risk.128 He also claimed that Anixter was a silent partner in Larman’s, perhaps the highest-profile gambling den in Maxwell Street and that he’d had a hand in threatening a Tribune employee who’d helped expose it in a notorious raid from 1913. Beyond revealing Anixter’s otherwise hidden hand in those well-known scandals, Green argued that Anixter pursued a deliberate strategy of avoiding the press. He claimed Anixter discouraged newsboys from selling the Tribune anywhere near his businesses, that he “circulated the wild rumor around the West Side” that the Tribune had attempted to extort $500,000 from US Senator William Lorimer, and that he boasted he had things arranged to keep his name out of the paper. That general point seemed important to Green, who gets hyperbolic in his letter, and he appended a handwritten postscript claiming Anixter had also ingratiated himself with several City News Bureau reporters.129 The lead of that unwritten story was straightforward: Anixter managed to hide in plain sight of the people of Jewish Lawndale. For a brief period in the early Lawndale years, Anixter could not avoid all publicity, even when his connections insulated him from prosecution. Healy’s successor as chief of police, perhaps embarrassed by his predecessor’s disgrace, set out to catch all the leading district gamblers at the end of 1919. Captain James Gleason himself led twenty-five officers in simultaneous raids on six different gambling joints in order, as the Herald and Examiner put it, “to preclude, if possible, a tipoff by the elaborate system said to exist among the gamblers.” The raids netted seventy-five suspects, including several prominent local gambling bosses. They found Davey Miller and eleven others at 3216 W. Roosevelt. They got Louis Klein and Henry Bollotin, who ran a place at 1210 S. Kedzie, along with twenty others, and Barney Ehrlich, whose place was at 3253 W. Roosevelt, with five others. They arrested William “Irish” Anixter, Putty’s brother, and a dozen more at 1343 S. Kedzie, and they pulled in thirty-seven others at Anixter’s Lawndale place. Still, they didn’t find Anixter himself. As the reporter editorialized with obvious disappointment, “It may as well be said now, before we get any further, that the ‘biggest fish’ got away. It was rumored that he learned of the contemplated

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raid early in the evening and found it convenient to be away from his place of business for the night.”130 Even without bringing Anixter in, though, the raids gave a remarkable picture of what Lawndale gambling was like and of Anixter’s chief place in it. According to the Herald and Examiner, Davey Miller’s and Bollotin and Klein’s locations each netted $2,000 a month, while Ehrlich’s took in $3,000. Meanwhile, Anixter’s new place was supposedly good for $4,000 and his old one for $6,000. Those are just estimates, but they suggest that Anixter made substantially more than his leading competitors combined. He was, indeed, the biggest fish and that was chiefly the product of his holding the lion’s share of the political protection of greater Lawndale.131 The biggest story of Anixter’s career came in the early 1930s, but it took place almost without any documentary evidence. That is, he made his peace with the larger Syndicate of the city. Most of the coverage of the gang wars of the second half of Prohibition dealt with the ways the Syndicate and the North Side Gang fought over booze. Much of what attention remained went to the scourge of racketeering, which passed heavy expenses onto consumers. That left little for attending to the gambling that was Anixter’s core concern. A rare example of such press coverage came in 1933, when an apparently out-of-town United Press reporter thought to ask what would become of the Syndicate once its booze profits evaporated with the end of Prohibition. The answer, the ensuing story reported, was that “what is left of the once powerful Alphonse (Scarface Al) Capone group” would move into gambling. “The next step will be to ‘muscle’ into the Anixter-Johnson gang of gamblers or ‘muscle’ that clique out of existence,”132 it claimed. As Robert Schoenberg tells it, though, the Syndicate threatened Anixter’s west-side partner William Skidmore, sensing their group would be more amenable to leaving the loose remnants of the North Side Gang’s alliance. It took some yelling and a bomb or two, but the arrangement was mutually beneficial. The Syndicate consolidated its hold at the expense of its remaining enemies, and Anixter and his partners retained the operations he’d begun twenty years earlier with improved political connections.133 It’s hardly a coincidence that Davey Miller, whose clout had waned even before then, found himself around the same time having to sell the M&E to Anixter’s lieutenant, Benny Zuckerman. That is, Anixter’s accommodation with the Syndicate cemented his authority in Jewish Lawndale, leaving no room for what was left of Miller’s organization. The result was that Anixter made his peace with the Syndicate as it moved from its Capone days to its modern form under Frank Nitti and his successors in the Outfit: Paul Ricca, Tony Accardo, Murray Humphreys, and Jack Guzik. The

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proof of that peace was that Anixter was still standing and that he still held the “concession” that Zuckerman would boast about a decade later. If Jules Portugese had never really made it out of Maxwell Street and Davey and Hirschie Miller had fallen just short of sustained criminal careers, Anixter positioned himself to melt into the larger confederation forming around him. He took his place in organized crime through the Syndicate and in politics through the Arvey faction of the Democratic machine. So, with even less attention than he got in the days that he was establishing his foothold in Lawndale, he settled into the quiet career of a behind-the-scenes power. The more time passed, the more Anixter seemed insulated. When he was arrested in 1920 alongside Davey and Hirschie Miller, Chief of Detectives Michael Hughes declared, “Sooner or later we’ll teach these criminals that Chicago isn’t a safe place for them.”134 Tough as the detective might have intended his remark, it clearly implied he was frustrated with earlier efforts. In 1924 a brief note in the Tribune referred to Anixter as a “high priest” of graft, someone who was “a general fixer and go-between for the politicians, the ward bosses, and the gamblers generally,”135 but that was just his reputation. They simply couldn’t make anything stick. Once he was insulated, Anixter let others run the risk of arrest and violence, and he found willing volunteers in the young Benny Zuckerman, Ben Glazier, Willie Tarsch, and Louis Dann. Anixter may have been vulnerable in his early years in Lawndale, when it was just turning into a Jewish enclave. Once the community was fully established, once Anixter had all his connections in place, he made himself the man to see if you wanted protection from the police or competing interests. The more he retreated from the publicity that might have harmed him, the less anyone could lay a glove on him. The only way to get to him might have been through the tough guys who carried out his interests. And those shtarkers, the young Zuckerman among them, bet they had a better chance at wealth and influence siding with Anixter than siding with the police or anyone else acting in the name of the civic side of Lawndale’s rise.

V That was almost the end of Anixter’s story, and it held for close to a quarter century. A major crack in his arrangements started in 1940, when William Skidmore was indicted and then convicted of tax evasion. Anixter put up bail for Skidmore, using his own home as surety, but he was likely more aggravated to see his name

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in the newspapers again. Called “someone whose name is often coupled with Skidmore’s when gambling is mentioned,” the article marked his first appearance in the Tribune in more than fifteen years.136 More ominously, it suggested his vaunted connections were beginning to fray. Tax evasion got Al Capone, after all, as well as many less-well-known Chicago organized-crime figures, and if the government was after Skidmore they were likely looking at him too. He was back to being a target again. A year later, in 1941, Anixter’s place was forced to close during an investigation by Illinois Attorney General George Barrett. Several other “big fry” got raided as well: Dennis Cooney, Hymie Levin, and Jack Guzik’s brother Harry, but in a sense they were old-timers, all characters who’d been absorbed by the Syndicate as it spread its model of confederation.137 With the winding down of the profits that even legal alcohol had brought, with the start of World War II and its changing patterns of consumption, and with the general aging of the men who’d pulled the Syndicate together, the old model was changing. Maybe Anixter saw it, and maybe he didn’t, but things weren’t going to be able to stay the way they were. When Anixter died at his home on December 20, 1943, he stood as the power behind the throne of Chicago’s independent Jewish gangsters, the man who’d most successfully ridden the early violent years into full confederation with the Syndicate. At fifty-eight years old, he’d no doubt looked as if he would stick around a while longer, but it’s also possible that the Syndicate he’d managed to become confederated with had other plans. The next couple of years would see a wave of murders of old-timers like himself: Danny Stanton in 1943, Vincent “Dago” Mangano in 1944, and James Ragen in 1945.138 A rising Syndicate assassin named Lenny Patrick would be a suspect in many of those killings. And a longtime Anixter associate—and principal heir—would have to negotiate those changed conditions without him. It was going to be a tough, and fairly short, road for Benny Zuckerman when it came his turn as boss all by himself.

5 RISING IN THE RANKS

I In his later years Bernard Neistein liked explaining how west-side Jewish politics was done. He’d give a roguish grin, take a puff on his cigar, and regale younger listeners with stories of hustling precinct captains lining up votes for the Democratic machine. The longtime greater-Lawndale-area politician outlasted Benny Zuckerman and most of his other peers from the 1940s and 1950s, and he seemed to feel there was no longer any point in hiding anything. He admitted, for instance, that he routinely lied under oath to help immigrants establish citizenship.1 Once he’d performed such a favor, people didn’t forget at election time. “If you were there every day, when they had sadness or when they had pleasure, the people remember that,” he said.2 Or, as he put it more bluntly on another occasion, “Immigrants made me the best precinct captain in Chicago.”3 Under the Chicago system precinct captains were the point people for delivering the vote, and they did it by aggressively cultivating relationships. What they did was legal; how they did it was often not. They answered to the ward committeeman, who was more powerful than, though sometimes the same person as, the ward’s alderman,4 and they competed among themselves through the margins they piled up for their candidates. Neistein’s longtime colleague Marshall Korshak, brother of reputed Outfit figure Sidney Korshak, waxed lyrical when he declared, “The precinct captain is the unsung and unheralded hero of our democracy.”5 Politics, for them, started at the local level and rarely got much beyond it. It dealt with cracked sidewalks and trash removal, and the side that best provided city services got the bonus of being able to deliver votes for its senatorial, gubernatorial, and presidential candidates.6 And, of course, it dealt with patronage hiring, an open dirty secret that Korshak called “disgraceful” even as he justified doing it himself.7

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The Democratic majorities coming out of Chicago’s Jewish wards from the middle 1920s into the late 1960s were so staggering that almost no one trusted them. While it’s true that precinct workers were convicted of voter fraud every now and again,8 Neistein insisted that the tallies were mostly legitimate. He claimed that in 1955 he delivered a 600–3 majority for Richard J. Daley—in a primary against a sitting mayor from his own party—and that he did it with poll watchers over his shoulder. Another time he insisted that he produced a 300–0 edge for his candidate.9 As he told the Tribune’s Ron Grossman, the totals were so lopsided he sometimes instructed election judges to add a few votes to the Republican total so the numbers would be more believable.10 The trick, as Neistein described it, was to be the smiling face of city government, to overcome the “maze of bureaucracies and regulations that lost the common touch.”11 But behind that smile lay the implicit menace of real power. The pioneers of questionable Chicago electioneering, longtime 1st Ward bosses “Bathhouse” John McLaughlin and Michael “Hinky Dink” Kenna—who reputedly fixed the price of a vote at 50 cents in the 1880s—famously had squads of tough guys to punish anyone who broke the contract.12 By the end of their extraordinarily long careers, they’d become functionaries of the Syndicate with its whole roster of thugs and killers at their implicit call.13 From that turn of the century forward, Chicago had a tradition of gangster-politicians, figures who were elected or who stood by elected officials with the butts of their guns essentially visible. The city was littered with intimidating figures playing the precinct captain or ward-boss role, from Manny Abrahams and Morris Eller in the Maxwell Street area to Dean O’Banion himself, of whom it was famously asked and answered, “Who’ll carry the forty-second and forty-third? O’Banion, in his pistol pocket!”14 So Neistein knew very well that, while he smiled for the public, he had to project an image of strength to maintain his position. “I wouldn’t say I’m tough. I’d have to have others say it for me,” he grinned. That part of the equation was as essential as a firm handshake. For all his cajoling, he also had to be someone his constituents feared, at least a little. They had to understand that, as much as he was there to listen to them, he was also responsible for keeping the powerful in power. And that meant nodding in the direction of the men who organized crime. He’d listen and he’d do favors, but eventually his constituents would have to go along with his program. “I’ve never had any problems in all the time I’ve been [in the ward],” he summed up one interview. “I’ve threatened to throw a few from the window, from the twentieth floor here in my office, but aside from that, it’s been very quiet.”15

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He was joking about throwing people out the window . . . probably. But others were deadly serious.

II As a precinct captain himself, Benny Zuckerman once beat up a former alderman during an election campaign. His victim, Leonard Grossman, was a strange duck. Although Jewish and active in Jewish causes, he was a staunch supporter of a declared KKK figure who’d come to Chicago to head up an elaborate scam.16 Appointed as a Democrat to the city council in 1927 to help resist the Caponebacked mayor, Big Bill Thompson, Grossman promptly switched parties to support the clownish incumbent.17 Once out of office he drew scorn for continuing to find ways to pocket public money through his role as an expert witness, and he stood as one face of governmental waste.18 Still, he was a public figure, and he had a measure of standing. There was even a term for what Zuckerman did: “slugging.” Just as it implied, it meant the physical intimidation of someone in the course of electioneering, and it was the standard in political menace. If you crossed the Machine, especially when voters were headed to the polls, you stood a good chance of getting punched or worse. As the 1932 elections were heating up—elections that would see Chicago’s West Side garner huge majorities for first-time presidential candidate Franklin D. Roosevelt—the Democratic machine pulled out all the stops. Grossman was campaigning for the Republicans in the company of two county patrol officers when Zuckerman attacked him violently enough that he was eventually charged with “assault to kill.”19 That’s how they played politics on the West Side, and Zuckerman’s ferocity was a key part of the Machine’s muscle. And the Machine did little to hide the fact that Zuckerman was one of their key operatives. The day after the assault, Moe Rosenberg, the most powerful politician in Lawndale, showed up at the courthouse in person with a writ of habeas corpus to have Zuckerman freed from custody.20 From there, Jacob Arvey, the ward’s alderman and eventually the central political figure of all Jewish Chicago, personally served as his attorney. Arvey got an immediate continuance on a trial date, keeping Zuckerman unencumbered until after the election. He was helped in his petition to the court when the two patrolmen alongside Grossman—presumably having been “spoken to” by Zuckerman’s allies—claimed they could not recognize Zuckerman as the man who’d perpetrated the assault.21 In other words, Rosenberg

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and Arvey could shake all the hands held out to them and cut all the ribbons their aides put up to celebrate new projects, but Zuckerman trailed them like a leashed Doberman as a reminder that public relations were only a mask for an always potentially violent political organization. That arrangement worked both ways, of course. In his turn, Zuckerman had Rosenberg and Arvey at his back as he went about his illegal activities. In what seems a brazen move, but that more likely reflects a reality so established that he figured it was a fact everyone knew, Zuckerman discussed the process with investigators from the Chicago Crime Commission on September 24, 1943. He explained that Lawndale’s 24th Ward, alongside two others in the same vicinity, essentially swung citywide campaigns. Since he was a proven vote-getter, since he boasted that he “practically succeeded Arvey as the political boss and [was] keeping the ward together” until Arvey came back from his World War II army service, he understood himself as calling all the essential shots. Through his political work, he had, he declared, earned the “gambling concession” in the ward.22 Zuckerman’s position as enforcer and gambler-in-chief was public knowledge because it functioned by being something everyone “knew” but that never quite rose to the point of legal prosecution. Just as his high-profile role invited law enforcement scrutiny, it also made clear his places were “safe” for prospective gamblers and the lower-level functionaries who made the games work. His standing, in effect, advertised on behalf of his business and against competitors that might try briefly to compete with him. As Crime Commission director Virgil Peterson put it soon after Zuckerman’s murder, fighting organized gambling was not merely a “moral or a reform” effort. It was not, in other words, Prohibition redux. It was a matter of cleaning up the electoral system so the city could be a real democracy. As Peterson put it forcefully, “Organized, protected gambling, as it has flourished in Chicago and Cook County, is organized murder. It is organized extortion. It is organized racketeering. It is organized vote frauds, and it means organized widespread corruption.”23 Gambling wasn’t a problem for what it was— whether a “sin” as reformers saw it or just another business transaction as others might argue—but for the political corruption tethered to it. The Tribune echoed that sentiment but added a wearied frustration that the likes of Zuckerman reflected a civic rot they’d been pushing against for more than a generation. As they editorialized, “[Peterson] mentioned precinct captains who run loop gambling houses. It is well known that it is futile to start a gambling house without the approval of the Democratic ward committeeman. The handbooks provide the Democratic machine not only with graft but with jobs also.” Zuckerman’s fame, or notoriety, allowed him to serve the politicians who granted

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him his place by displaying political spoils and by providing an illegal service that much of the public wanted. As they concluded, “Chicago gambling crusades are the sham battles of factional politics. We have investigations aplenty, but who ever goes to jail?”24 In other words, Chicagoans knew who the gangsters were—the Tribune told them on a regular basis. Those gangsters may not have enjoyed the harassment, but they benefited from their fame in being recognized as the de facto government of the routine lawbreaker. Some of Zuckerman’s political ties were real and documented, and they went back to the beginning of his time in Jewish Lawndale. He’s listed as a clerk of elections from the 24th Ward’s 16th precinct in a directory from March 1924.25 When he was charged by police with carrying a gun illegally in 1928, he produced “a star and identification card” demonstrating he was, in fact, a member of the sanitary-district police.26 Less certain but just as real was his reputation as one of Arvey’s lieutenants, a fact most news stories about him acknowledged.27 Or, as the Chicago Sun put it, “Arvey’s ward workers spent so much time in Zuckerman’s café, the R&K Restaurant, at 3215 [sic] Roosevelt Rd, that the place became known as the unofficial ward office and persons seeking political favors went there to petition office holders.”28 Zuckerman’s real connection to 24th Ward politics never made it fully into print, though, since his job represented the dark side of machine “democracy.” When he “slugged” Leonard Grossman, the story was so commonplace that the Tribune never reported it, mentioning it only years later when Zuckerman had been arrested for something else.29 Imagine the implications of that fact: if it was a dog-bites-man story when Zuckerman beat up a former alderman in the middle of an election campaign, how much less newsworthy was it when he “leaned” on an ordinary citizen who might have had a complaint about Arvey or one of his preferred candidates. Other wards, home to other ethnic communities, routinely saw the same kind of violence. That was simply the nature of a Chicago politics that depended on the precinct captain’s smile as well as his fist. It reflected a time in the city when election violence was so ordinary that it had a simple name, when a violent man could ride his menace into political power and significant wealth.

III And Benny Zuckerman was a violent man with a wicked temper, the sort who could assault a waiter for no apparent reason.30 The first time he seems to have made the papers came in 1921 when, as a messenger for a west-side macher or

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big shot—possibly Putty Anixter—he was robbed at gun point. He held a satchel with $3,500 and was being driven by someone else, all of which suggests that the person who dispatched him suspected the possibility of an attack. As the car drove east toward the Loop, an unidentified man leapt on the running board “while flourishing a revolver in the messenger’s face.”31 The robbers got away with the money, but the experience suggests the everyday violence of Zuckerman’s early world. He was, the story suggests, a tough guy tasked with a tough job. If he didn’t pull it off that day, it’s certain he did so on many other occasions. On March 16, 1927, in an incident that foreshadowed his eventual murder, two gunmen caught up with him just as he was entering his apartment building at 1339 S. Lawndale. Hearing noise from across the street, he turned just in time to see a sawed-off shotgun go off. Three pellets hit him, one in the face, as he stood in the vestibule, key in hand. It was a particularly bloody week in Chicago with four gangsters gunned down in the previous few days,32 so newspapers covered it with a palpable weariness. The Tribune blandly but brutally reported, “One of the men leveled the shotgun at him and fired, three slugs taking effect, one of them in the face.”33 A wire story from the same day put it so concisely that it sounded routine. “Benjamin Zuckerman, 33 years old, restauranteur ostensibly, but an ‘alky runner’ by word of the police, was shot, probably fatally by two men with shotguns.”34 Zuckerman recovered, but like most gang violence from the time, the assault remained officially unsolved. In this case, though, police discovered a telling clue. Though critically injured, Zuckerman refused to go to nearby Mt. Sinai Hospital, insisting instead on St. Anthony’s. An enterprising policeman, Sergeant Philip McInerney, went to Mt. Sinai himself and found two known “bitter enemies of Zuckerman” in waiting, presumably intending to finish the job. They were Peter Saronoff and Alex Portugese, brother of onetime Maxwell Street “scarface” Jules Portugese. As the wire story reported, both were connected to Maxie Eisen, a gangster allied with Dean O’Banion’s old North Side Gang.35 The gangster politics behind such an attack were Byzantine. At the time, Zuckerman was running a club at 1227 S. Kedzie, back in the Maxwell Street neighborhood. As a consequence, Alex Portugese may have intended to assert his right to the turf. It’s also possible that Portugese was seeking revenge for his brother’s murder eight months earlier, suspecting Zuckerman of some involvement. Perhaps Portugese was making the same sort of play his brother had, figuring that taking out Zuckerman might give him an opportunity to move into Lawndale. And it’s also possible the shooting was simply a skirmish in the rising showdown

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between the Capone Syndicate, with which Zuckerman was more or less allied through his Lawndale connections, and the North Side Gang, then headed by Bugs Moran. The bottom line was simply that shootings and killings happened. The gangsters seemed as inured to it as the reporters typing up the stories. But the most telling violence of Zuckerman’s rise to power came early on November 11, 1928, when he and his partner Ben Glazier—who would die of a heart attack the same night that Zuckerman was murdered—were involved in a car accident with John “Doc” Acher, a reserve football player at Northwestern University. Acher and his sixteen-year-old brother had gone to a number of nightclubs to celebrate the team’s 7–6 victory over Purdue that day, a game where Acher had played in the fourth quarter. The two drove down Michigan Avenue to 14th Street, a reputable stretch of town a bit north of Capone’s headquarters and less than a mile from Maxwell Street. The collision was minor, leaving the gangsters’ car with little more than a damaged fender. Acher and the men had a brief argument, then he drove on. He turned around a few blocks later to see the gangsters following him; one of the two was standing on the riding board of the car with gun drawn. He pulled over at their urging, and then the gunman, apparently Zuckerman, fired three shots, and Acher slumped over at the wheel.36 Zuckerman and Glazier took off immediately, but police pursued them in and around the Loop for almost five miles before one of the two motorcycles in the chase broke down and the second officer feared going forward without backup. Solid detective work over the next couple of days identified the two after they dropped their car off at a garage for repairs; some early reports had it that there were two or three other men in the car, but they were never identified and later reports didn’t mention the fact again. It turned out Acher had been hit twice, once in the thigh and once, more seriously, at the base of his spine. He was not only paralyzed from the waist down but also vulnerable to infection. Doctors debated whether to operate or make him as comfortable as possible—at the request of Northwestern’s administration, they even consulted one of Britain’s leading surgeons, a man who happened to be visiting Chicago at the time—but there was nothing they could do. Acher spent the next several months in and out of hospitals and confined to a wheel chair. He died on May 19, 1929, four days before his twenty-second birthday, and his family buried him with a Northwestern athletic letter blanket by his side.37 It was, in other words, murder—and murder not of some gangland tough, but of an upper-middle-class college student, son of the leading physician of

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Fort Dodge, Iowa. Zuckerman and Glazier were the only suspects in the murder, pointed out by an eyewitness and linked to the car that ran into Acher’s, but the charges against them were dropped when neither Acher brother would formally identify them as the killers. The most likely way to read the incident is as evidence of Zuckerman’s fierce temper. As one story put it, “Gunmen’s bullets [served as a] hot-headed answer to a minor automobile accident.”38 And as the Daily Northwestern wrote, “Speedy justice, students say, demands that the men who shot to kill over an accident in which damages did not exceed more than $12 be quickly brought to task.”39 Put in such a light, this was who Zuckerman was: a man with a murderous temper who, sensing himself invulnerable thanks to his political and gangster ties, knew he could get away with almost anything. There are a couple loose ends to the case, however, and they suggest another way to interpret Zuckerman’s crime. To begin with, Zuckerman had stolen the car he was driving.40 That implies the damage should have meant little to him and opens up the possibility that he was intent on committing a crime that night. Then there’s the fact that Acher played for a major sports team less than a decade after the infamous Black Sox scandal, in which gangsters and professional gamblers conspired to throw the 1919 World Series. There was a tradition, somewhat curtailed by that point, of gamblers taking an interest in college football, particularly in the Big 10 conference,41 and Northwestern’s team was compelling enough for Chicago’s gangster elite that Al Capone regularly attended games, including one on October 4, 1931, one of the last days he was at liberty before his conviction for tax evasion.42 In a reading supported only by circumstantial evidence—including for instance the fact that the prosecution petered out as it did—it’s possible that Zuckerman was angry with Acher over some form of double-cross in Northwestern’s victory that day. Again, nothing from contemporary reports suggests the slightest whiff of such controversy, and it seems patently unfair to impugn a young man murdered ninety years ago. The point is simply that Zuckerman may have been even worse than a killer unable to control his temper. He may have been someone willing to plan and perpetrate the murder of a young man, in many ways a child, someone he barely knew. And such a cold-blooded figure would have been even more dangerous than one driven only by white-hot anger. Any way you read the evidence of his crimes, the Zuckerman who rose to power in Lawndale in the 1920s was a frightening man. With him on their side, the neighborhood’s politicians could intimidate all the voters they needed.

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IV And then, slowly, Zuckerman wasn’t so frightening. If the final years of Putty Anixter’s career showed him losing some of the touch that had allowed him to insulate his gambling operations for such a long time, it was even worse for Zuckerman. The political machine’s links to gangsters became increasing liabilities. The nature of Chicago’s machine politics was changing as the coalition that founded it matured and its members grew comfortable in their established offices.43 Arvey, in particular, had senators and governors to elect, and it didn’t help to be seen as attached to professional gamblers and thugs. At the same time, the confederation model of crime was giving way to the corporate one. Anixter and his lieutenants may once have held themselves out as independents in a city caught up in a criminal civil war, but they’d mostly made their peace with the Syndicate by the middle 1930s.44 Starting in the late 1930s, Zuckerman’s clubs began to be raided with more regularity, and there’s evidence of his losing some of his standing. On October 20, 1938, a police squad stormed his newly opened Roosevelt Road handbook using axes, and the Tribune identified him as having a minor police record and [someone who] is known as a lieutenant of Ald. Jacob M. Arvey, Democratic leader of the 24th ward.”45 A year later, though, that identification showed that he was drifting away from his patron. When Zuckerman was called before the grand jury that eventually brought charges against Anixter’s old ally William Skidmore, the paper claimed only that he “once rated as a political aid of Ald. Jacob M. Arvey.”46 By the time Anixter died in 1943, Zuckerman was negotiating a new equation for securing his own standing. He’d always need to get along with the local Democrats, but that was increasingly difficult with the rise of Arthur Elrod in the wake of Arvey’s time in the army. And just as the political machine was maturing, so was the Syndicate. There were new opportunities to work with his peers across the city, bosses like Vincent “Dago” Mangano, who also had strong satellite operations subordinate to but independent of the operations centered around Jack Guzik, Murray Humphreys, Paul Ricca, and Tony Accardo. He’d made himself a place in rough-and-tumble Lawndale, and he’d earned his gambling concession by loyal work. He could still pull it all off. They’d raided his R&K Restaurant in October of 1943,47and it was still shut down in January. Rumor had it that the Syndicate had offered him a deal: he could reopen with their blessing, but it would cost him 50 percent of the take, double

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the supposed rate of just a couple years before.48 That would make him subordinate in ways he never had been. It would have made him a functionary of that larger operation, no more than part owner of the operation he’d spent a lifetime building. The mob wanted to take over, but he wasn’t having it. Supposedly, he received an ultimatum: “the cut would go through ‘or else.’”49 Zuckerman stood firm, though. He’d been through tough times before, and he was prepared to keep fighting for what he’d earned. He announced that on January 18 he was going to reopen the restaurant and, implicitly, the gambling handbooks attached to it. Then, on January 17, the Syndicate, likely in the person of Lenny Patrick, caught up with him and shut down his operations for good.

6 ROOTS OF THE LAWNDALE MACHINE

I H. L. Meites looks pleased with himself. As he stares out of the portrait he placed at the front of his 800-page opus, History of the Jews of Chicago, he seems to represent, in his own person, the genteel Chicago that his book celebrates. He has a proud, trimmed mustache, a subdued pocket square, and a meet-your-gaze confidence. And, to be fair, his book is worth being proud of. As he reports midway through, many thought it a project that couldn’t be completed, and others felt that Chicago’s Jewish accomplishments were too meager to make it worth doing.1 Yet it stands as a substantial work of scholarship. Close to a century after it was published, it remains the go-to source of information for the rise of Chicago’s German-Jewish establishment, and it gives a useful look at the way its EasternEuropean newcomers were asserting themselves in the generation after their arrival. It celebrates hundreds of men and women with photographs and capsule biographies tracing their origins and highlighting their successes. It presents itself as the summation of the Chicago Jewish experience up to 1924. And it barely mentions Manny Abrahams. He’s there as Emanuel M. Abrahams in a list of Jews who served in the Illinois legislature, and he’s there two pages later as E. M. Abrahams in a list of Jews elected to the Chicago City Council.2 Otherwise, nothing for the first substantial elected representative of the Maxwell Street community, a saloon and gambling boss, a gang leader and politician who became the subject of national concern when he crossed lines to support a Republican senator and who eventually died in the midst of a floor fight to protect the rights of Jewish workers. Despite accomplishing all that during the very time Meites was pulling together

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materials for his book, Abrahams doesn’t make the cut for that encyclopedic, first history of the city’s Jews. Morris Eller makes it into the book, along with his son Emanuel, but there’s no mention of the voters they kidnapped or the rival candidate they murdered. Michael Rosenberg has an entry, but not his brother Moe, who would soon succeed him as boss of the early Lawndale Democratic machine. Jacob Arvey gets included, but it’s so early in his career that he may be the youngest person in the book to warrant his own biography, and there’s no hint of his connections to men like Benny Zuckerman. And good luck finding Putty Anixter or Davey Miller. The reason for such oversights and diminished attention is simple. Meites set out to celebrate a community on the rise but only on the trajectory he valued. As his portrait suggests, he wanted to demonstrate that Chicago’s Jews had accomplished enough to have a claim on the city. He wanted to answer an anti-Semitism that depicted Jews as disruptive socialists, anarchists, or criminals. To his credit, he cast his net beyond his personal circle, but he couldn’t quite see the dramatic change in demographics and fortune that the next generation would bring. He couldn’t predict the great cultural, commercial, and yes, criminal energy that would rise out of Chicago’s Ghetto. He celebrated a history that he saw culminating on the Gold Coast with its millionaire mansions open, at last, to dozens of Chicago’s Jews. He didn’t realize, though, that much of the future lay further west, first in Maxwell Street and, not long after, in greater Lawndale, and that its roots lay in a complex of politics and crime that created and depended upon a generation of Jewish gangsters. He’s looking forward in that picture, but he’s missing the ferment beneath him.

II Manny Abrahams rode that ferment to become the alderman for Benny Zuckerman’s adolescent Maxwell Street ward. For that matter, Abrahams was a boss of the world where the toddler Lenny Patrick first stopped sucking his fingers and learned to make them into a fist. Abrahams got there using tactics that paved the way for Morris Eller and Jacob Arvey, but he did it in a cruder way, combining Bernard Neistein’s smile with Benny Zuckerman’s bludgeon, and then putting himself forward for election. In that simpler time he was a triple threat: cajoler, slugger, and candidate, the three key roles in any machine election. In retrospect, it was a straightforward, maybe inevitable, process but he deserves credit for being

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the first to pull it off in Jewish Chicago, the first to fashion himself into a fullblown gangster/politician hybrid. In his early years Abrahams represented a kind of upward mobility within the immigrant world, rising from peddler to saloon owner and, eventually, in the words of the Tribune, “gang leader.”3 He was hardly alone in starting as he did. Since the area was close to the fish-and-vegetable markets, many newly arrived Jews turned to the most basic of retail work, getting up well before dawn, stocking their carts with fresh goods, and venturing into other parts of the city. If they were fortunate, they had a horse; if not, they pushed or carried their wares themselves.4 It was hard and sometimes dangerous, and among many other fatalities, Arvey’s father died after a 1908 accident threw him from his cart.5 Those who survived endured indignities, and while providing necessary services in a city without the transportation we take for granted today, they often found themselves mocked or attacked as unwelcome outsiders.6 Abrahams was successful enough to open a saloon at 451 S. Halsted and later at 921 W. 12th, seemingly in the late 1880s or early 1890s. Such work meant he no longer had to roam the city to make sales, but it put him at the mercy of the municipality in a different way. There were laws prohibiting Sunday sales of alcohol—particularly irritating to Jews who observed a different Sabbath—and discouraging the gambling that he used to supplement his income. To get around those laws, he needed influence with the police and the politicians who controlled them. And to get that influence, he needed to become a politician himself.7 The equation was so straightforward that saloon owners of the period were already de facto political figures. “Hinky-Dink” Kenna more or less ran the 1st Ward out of his saloon,8 and others such as John Powers and, a bit later, Anton Cermak, came to power through their capacity to direct their clientele’s votes.9 Within what would become the 20th Ward,10 Abrahams cinched his eventual aldermanic election by sending an agent to negotiate a deal with a handful of saloon keepers he feared might push against him, promising things would be wide open for closing times and gambling.11 As Abrahams was getting started in formal politics in 1897, he signed on as an officer of a newly formed Chicago Tammany club, one that sought to model a Chicago politics on the New York bossism of William Tweed and Richard Croker, where saloons were a cornerstone of political organizing.12 He lost his campaign for president of Cook County Commissioners in 1898,13 but he secured a spot as clerk of courts at the Maxwell Street police station by at least 1902 even as he continued to run the saloon and oversee the illegal gambling

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going on at it.14 That put him in what the Tribune called “a sort of Jekyll and Hyde existence,” serving the courts in one capacity and then breaking the law in the other. As it went on, “his mornings are spent recording fines and frowning at rival gamblers and other evildoers who appear in Magistrate Sabath’s court. . . . After court adjourns he repairs immediately to his gambling dive and discards the personality of a part of the machinery of ‘justice’ and the police department and becomes the ‘good fellow,’ keeper of a gambling resort.” The gamblers there knew they were safe from a “pinch” since Abrahams had everything greased, and Abrahams himself had no diffidence in explaining what made his saloon so popular. “I’m in politics, you know, and I’m a drawing card,” he said.15 The Tribune’s exposé of his gambling operations cost Abrahams his clerkship, but he rebounded quickly and earned his greatest notoriety with election as a state representative in 1907. He got some legitimate work done on behalf of workers—taking the lead, for example, on legislation requiring licensing for barbers, allowing them to maintain their rates16—but everything paled before his vote to confirm Republican William Lorimer as US senator. Illinois had not yet moved to direct election of senators, so it fell to the state house. At the time, Abrahams’s Democratic party had the majority, which made it obvious they would go with a Democratic nominee. Rumors began swirling that there was a backroom push for Lorimer, but no one could believe it. What—other than the obvious, naked graft—could persuade enough Democrats to vote for the other party? Since representatives cast their votes in alphabetical order, Abrahams had to go first. When he voted for Lorimer, he stood out as the “bellwether,” the Democrat who made clear it was possible to switch party lines, and he took the lion’s share of the blame. It became a national scandal with editorials in publications as farflung as the Washington Times, Munsey’s Magazine,17 the Orangeburg, SC Times & Democrat, and the New York World18 calling him out, and a senator from South Dakota claiming that his name was “steeped in indescribable infamy.”19 Abrahams insisted, with at least some basis in truth, that he’d known Lorimer most of his life and that, in his early peddling years, Lorimer, a streetcar conductor, had often shown kindness and let him ride with his bundles against company policy.20 A year later, though, reports surfaced that Abrahams had been offered $2,500 for his vote but had held out for $5,000.21 Abrahams not only weathered the scandal but turned it to something of an advantage by insisting he could get along with both political parties. That was one of his lessons for Morris Eller: serving his constituents and himself—not necessarily in that order—meant being flexible, meant playing larger factions against

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one another. He’d done well for himself in Springfield, but the real prize had always been a seat on the city council. With it, he’d have the power of patronage hiring and, of particular interest in a ward so centered on peddling, control of the Maxwell Street market. To that point, Jews were a key constituency of what would become the 20th Ward, but they were only one bloc that the mostly Irish representatives fought over during campaign season. Abrahams saw a chance to win the ward as a Jew by allying with Mayor Carter Harrison, who, in the midst of the campaign to close the Levee, needed quiet and secure places for gambling to move. In 1913 Abrahams at last broke through and won a hard-fought election as alderman. His opponents in the primary bombed his saloon twice, once in a hard-to-fathom drive-by from a horse-drawn buggy.22 He gave as good as he got, though, notoriously using his pull with the Harrison machine to get a number of Maxwell Street policemen shifted to different districts as a thumbs-up to his would-be gambling confederates,23 and unafraid to turn to the sort of violence that Zuckerman would utilize in the following generation. As the Tribune observed drily, “fistic encounters” were common on election day,24 and Abrahams’s supporters were charged with “rioting.”25 In the primary that followed, the Inter-Ocean newspaper characterized him as having a “rotten record” and as being “totally unfit” for office.26 And all that was before it turned out he was squeezing payoffs from the Maxwell Street market27 and was part of a scheme to uncover the locations of future public schools so he could profit on real estate speculation.28 For all his boondoggling, Abrahams did have a real legislative agenda in the City Council, and he did represent the concerns of his working constituents when he wasn’t exploiting them himself. Early in his term, the council approved an ordinance prohibiting peddlers from yelling during the day. Supporters argued that it woke night-shift workers and brought distress to quiet neighborhoods. Abrahams stood against it on behalf of those toiling as he had in his early years. “The peddler don’t make as much noise as the automobiles on the boulevards,” he declared, and he insisted the ordinance was not only selectively enforced but an instance of anti-Semitism. The stand, a brave one, cost him his life. The hundreds of peddlers in attendance cheered him with “Good boy, Manny,” and as he basked in their praise, sweat dripping from his exertion in the midst of a torrid heat wave, he grimaced, staggered into his seat, and slumped to the floor. He had suffered what the coroner would call apoplexy and died hours later without regaining consciousness.29

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Abrahams’s death provided a punctuation mark to the skill he’d shown in knitting together a coalition of Jewish working-class interests with the backing of the gamblers of the Harrison machine. It had taken someone with a particular gangster temperament, someone tough, shameless, and charming, someone able to punch out an enemy but just as happy to pay a bribe instead. As a result, his coalition split without his particular gifts for uniting impulses at odds with each other. His widow, Fannie, representing a reform influence, put herself forward as a candidate to succeed him in the first election in which Chicago women could vote or run for office.30 His brother Morris, a noted gambler and slugger himself, ended up with the seat, which he promptly lost in the election of February 1914,31 and the ward returned to Irish and German control until Morris Eller’s rise a few years later. Abrahams himself, once a nationally notorious figure and, in the fleeting seconds before he died, a working-class hero, faded to a historical footnote, one that H. L. Meites could barely find room for in the history of Chicago’s Jews that he would write just a decade later.

III Three stories are revealing about Morris Eller, the man who picked up the pieces Abrahams left behind: The first took place one day in 1925, when a reporter for the Chicago American stopped by the Cook County jail to interview Terry Druggan, a major bootlegger from just outside the Maxwell Street area who was serving a one-year sentence. A guard apologized, saying, “Mr. Druggan isn’t in today.” It turned out that Druggan and his partner Frankie Lake had an arrangement permitting them to leave the premises when they felt like it. If they chose to spend the day in prison, they had all sorts of privileges, including the services of a guard as umpire when they felt like playing baseball.32 Warden Wesley Westbrook testified that Morris Eller had asked him to provide such treatment, and Eller had reportedly provided substantial bribes to make it happen. Westbrook and Cook County Sheriff Peter Hoffman were convicted, but Eller suffered no consequences.33 In the second, on August 10, 1926, North Side Gang bosses Hymie Weiss and Vincent “Schemer” Drucci were walking down Michigan Avenue in front of the Congress Hotel and near Eller’s offices when rival gangsters started shooting at them from a passing car. The two drew their guns and exchanged more than thirty bullets, wounding one bystander but suffering no injuries themselves. Drucci was

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carrying $13,200 in cash, earmarked, investigators determined, for Eller. Again, Eller escaped all legal entanglements.34 And in the third on November 2, 1926, when facing a difficult election day, the Eller campaign set up court, literally, in the home of Eller’s son, Emanuel, who’d been elected a Superior Judge three years before. Eller had sent out his usual cohort of election sluggers, but reformers from across the city got police to arrest many of them. Judge Eller directed the officers to bring the apprehended men to his “home court”—which meant they never had to leave the ward and be subject to other authorities—where he summarily dismissed the charges and released each man back to the fray. Among those set free were North Side bosses Bugs Moran and Vincent “Schemer” Drucci and future St. Valentine’s Day Massacre victims Frank Gusenberg and James Clark.35 So, yeah. Morris Eller was a real gangster. He may not have looked intimidating—he was short, dramatically mustached, and middle-aged—but he was connected to some of the most violent exchanges in the middle of the most violent era of Prohibition. He picked up where Manny Abrahams left off but took things much further. With the vast profits of bootlegging piled on top of what was already there from gambling, Eller had even greater opportunity. He played a long game, working his way from one political position to another over a quarter century, but he played it smart. He became not simply a city power broker but the leader of a gang willing to commit murder to keep him there. Eller was born in Libau, Russia, in 1866 and came to Chicago when he was already seventeen years old. He referred to himself in a 1918 campaign biography as a “real estate man,”36 though an early profile described him as a peddler who taught himself English and then bookkeeping, which enabled him to marry into his employer’s family.37 He learned the Chicago system quickly and by 1897 had secured a patronage position with the County Recorder’s office. Although the ward tended Democratic, Eller joined the Republican Party and slowly accumulated patronage power of his own. He would later be charged with accepting kickbacks from the people he hired, an exchange he obscured by presenting it as a voluntary charitable contribution, one that just never seemed to find its way to its purported beneficiary.38 Eller really began to move up during the political sea change of Big Bill Thompson’s rise. For most of the time between 1897 and 1915, Democrats held the mayor’s office under Carter Harrison, who functioned as the seemingly reasonable, blue-blooded face of a government that permitted crime only in out-of-the-way places like the Levee and, as it was gradually shut down,

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ethnic neighborhoods like Maxwell Street and the African American 2nd Ward. Harrison’s coalition fell apart, though, as reformers began to see him as too weak and his gambler and gangster allies found he no longer delivered the protection they paid for. Thompson challenged him with an unlikely coalition of the disaffected.39 As the most prominent Jewish representative of that coalition, Eller went through a succession of offices, often holding multiple positions at a time to increase his opportunity for patronage: 20th Ward Republican committeeman by 1912,40 city sealer in 1915 and clerk of courts in 1918. Those positions were only stepping-stones, however, and Eller got his real reward in 1920, when he was anointed the Thompson machine’s candidate for Metropolitan Sanitary District trustee, a position with a massive budget for hiring.41 Eller won that election so handily that it drew attention from multiple better-government observers. As Col. John V. Clinnin, head of the fraud prevention and detection bureau of the Chicago Bar Association, put it, “In one precinct of the Twentieth Ward, there were nineteen more votes cast than show on the poll book. In other words, workers for the machine slipped nineteen ballots into the box and expected to put the names on the books later, but they were watched so closely they had no opportunity to finish their job.”42 That means, of course, there was no telling how many votes they had gotten away with stealing. Eller repeated that election chicanery in 1922, when he arranged to have his son elected as judge in an election where the Chicago Bar Association declared Emanuel Eller unfit for office and, in a straw poll among its members, ranked him thirty-sixth out of forty candidates.43 Under an unusual provision that the city soon abandoned, unregistered voters were eligible to cast ballots if they signed an affidavit affirming their residency in the precinct. Given the history of fraud in the 20th Ward, that was a license to print votes. In the 11th precinct, where 429 people were registered, there were 674 votes for Manny; that is, 57 percent more people voted for him than were originally registered. The numbers were only slightly less outrageous in other precincts.44 The more Eller won, the more resources he collected. Through the patronage he controlled he could mobilize an army of campaign workers to ensure the candidates he supported got into office. University of Chicago sociologist and better-government advocate Carroll H. Wooddy estimated that Eller controlled as many as fifty-three permanent political jobs, not including temporary election-related positions. Since each of those workers could undoubtedly call on family and friends for further support, that meant there were hundreds of people available. As Eller told Wooddy, “We get pretty nearly a unanimous vote from the

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Republicans.”45 And Eller saw no reason to apologize for his methods. He told a special US senate committee in 1926 that he thought his organization was “wonderful; the best in Chicago.” When asked how his organization was comprised, he answered, “Job hunters and my personal friends.”46 And, of course, Eller supplemented those semilegal supporters with his shock troops, a second army—this one actually armed—of sluggers willing to shoo away or slug anyone who dared to investigate an election, mount too serious an opposing campaign, or sometimes, simply vote the wrong way. Some of those gangsters were his own family—his nephews Abe, Martin, and Nathan Klass were responsible for bombings on behalf of his campaigns47—and some were professionals for hire, like Harry Hochstein, who would go on to a long career in the Syndicate; Sam Kaplan, onetime best friend and partner of Jules Portugese;48 or Meyer Mackenberg, uncle of Lenny Patrick.49 Others like Hirschie and Davey Miller were more loosely affiliated, paying originally for gambling protection and then, with the advent of Prohibition, for the concession to sell booze.50 Collectively, they were at times referred to simply as the “20th Ward Group” of Jewish gangsters.51 To pull such different gangsters together, Eller relied on his role as a significant go-between for the often-warring North Side gangsters and the Syndicate. As a Thompson ally, he was linked to the Capone people; as an old hand from Maxwell Street, he had connections to the Jewish figures who handled much of the North Side commercial and racketeering interests: Max Eisen,52 Paul Morton,53 Julius Kaufman,54 Frank Foster,55 and Ben Jacobs.56 Those allegiances almost certainly meant there was no room for Benny Zuckerman in the Eller forces. As someone allied with the neighborhood ethnic machinery of Anton Cermak and Jacob Arvey that would supplant the Thompsonites, Zuckerman was on the other side politically. As someone who’d feuded with the Jules Portugese gang, which the Eller group largely absorbed, he was on the other side criminally. As a bottom line, Eller pulled together the largest Jewish gang in Chicago’s history, the 20th Ward Group, some of whose remnants would eventually make peace and join with Zuckerman further west in Lawndale. In retrospect, Eller looks very little like a Jewish Capone. He was not, after all, any sort of reckless “Scarface”; he did not wave a tommy-gun in the faces of the rivals who tried to stop him. He was, however, a master of organized-crime confederation. Through his connections to Thompson, and through those to a Syndicate alliance that gave him support from the city’s leading gangsters, he took his place as an independent figure benefiting from clear alliances. So long as the Syndicate could keep Thompson as mayor, they could buy themselves the political cover they needed to

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operate with near complete freedom. Eller wasn’t merely a corrupt politician; he was someone willing to take part in the violence that made the system go. He took his opportunities from the model Johnny Torrio put forward, though recognizing that real power came from organizing crime to bring in bootlegging, gambling, and kickback profits at a steady rate. After that, he had his army ready to cajole and slug any time the “democratic process” called for it.

IV When Eller ran for reelection as ward committeeman in 1928, he faced the most uphill campaign of his career. Thompson had been reelected to a third term only the year before, but voters were rapidly tiring of the gangster violence that seemed to consume the city. In the 20th Ward a coalition of reformers and Democrats lined up behind Octavius Granady, a well-spoken African American attorney who looked likely to draw most of the ward’s black votes. As Eller distanced himself from Thompson, he had less opportunity to call upon the Syndicate toughs he had counted on in the past. To win this one, he was going to have to take personal charge of what amounted at times to an armed conflict on the streets of Chicago. According to later testimony, Eller convened three dozen of his men the night before the voting. He rallied them by declaring, “Don’t be afraid. You’ve got the governor, the state’s attorney, and the sheriff with you. I’ll take care of the police— and if you need him you’ve got a judge.” The judge, of course, was his son Emanuel, and Morris had proved he really could control the local police.57 And this was more than simply go-get-’em enthusiasm. As one participant later reported, Eller went on, “Any of you boys that don’t have guns can get them at Emanuel’s house.”58 They were making plans for an assault, not an election campaign. April 11, 1928, was a long day for the Eller opposition. As one example, a poll watcher observed a pair of Eller loyalists altering the official poll book and witnessed several people voting without proper identification and arriving at the poll with ballot-like pieces of paper that already had x-marks indicating their choices. The election judges on duty, David Feinerman and Sam Brin, had produced a 403–1 result in favor of Eller in the last election they’d worked, and they seemed to be at it again. The poll watcher flagged down the first police officer he could find, but the officer explained he had “promised not to bring Feinerman and Brin in.” A second officer from outside the ward agreed to arrest the men, but Emanuel arrived and, this time in the middle of the street, convened his court and found

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the men innocent without bothering to hear testimony from either side. Such corruption had the backing of clear violence, though, with the poll watcher explaining that Morris Eller, who arrived later, held his hand to his hip, implying he was carrying a gun.59 Throughout the day the Eller gang sent cars all around the ward intimidating and slugging where they thought necessary. In several cases, they simply kidnapped people at gunpoint and brought them to a shanty located at 1352 S. Peoria, within a block or two of Emanuel’s home.60 The eventual investigation identified at least a dozen and perhaps as many as twenty people who’d been held in the house by armed guards until after the polls had closed. Roughly half the kidnapped men were African Americans, and at least two reported they had been beaten up.61 Afterwards, each was free to go his own way, but the gang warned them not to discuss the ordeal. Most heeded the warning. A few needed additional persuasion, but they also eventually decided against testifying. The Defender, Chicago’s leading African American newspaper, recorded the otherwise unreported detail that one Eller tough had a gun pointed at the head of an African American supporter of Granady and was saved only when a policeman knocked his arm aside before he could fire. Afterwards, “the policeman neither arrested the gunman nor took his gun away.”62 Such tactics mostly cleared the streets of Eller opposition, but Granady himself was another matter. He, too, drove around the ward, rallying what supporters he could find. Since he was supported by the still-influential Charles Deneen, he was not without resources, but even a US senator was out of his depths in this kind of politicking; election violence was so widespread that someone had bombed Deneen’s own home months earlier. Eller gunmen, driving in a convoy of at least two cars—perhaps there were as many as four—spotted Granady and sped after him. After a few blocks, they forced his car to the curb, and he got out and ran. Suddenly, rifle barrels sprouted from the Eller cars’ windows, and machine guns spurted. Granady fell instantly. Some reports suggested a gunman got out of the car and fired a coup de grace; others said the cars just kept going. The Eller cars sped off, but they were hardly inconspicuous. Draped with bunting and other election decorations, they bore large banners urging people to reelect Morris Eller as 20th Ward committeeman. The last thing some witnesses to the murder saw was Eller’s own face prominently pictured on the backs of the receding cars.63

7 ARVEY’S BALANCING ACT

I Davey Miller was in a festive mood on April 6, 1915. He was twenty-five years old, a moderately successful heavyweight boxer, and the owner of a pool hall at Roosevelt and Kedzie, and the election returns were everything he could have wished for. Big Bill Thompson, the Republican candidate for mayor, had won in a landslide on a campaign that gave wink-wink approval to wide-open gambling.1 Miller and his brothers already had Maxwell Street ties to Morris Eller,2 and he knew he could buy protection from that channel. Prohibition was beyond the horizon—who could imagine teetotalers would change the Constitution—but Miller could see boatloads of money coming his way in a Lawndale on the brink of becoming a major center of Jewish life. Legend has it he called a team of bricklayers that very day to build out the second story of 3216 W. Roosevelt Road for the rooms that would constitute the heart of his, and eventually Benny Zuckerman’s, gambling enterprises.3 From a Chicago Jewish gangster perspective, that day can serve as the Fourth of July. There aren’t any records for how Lenny Patrick spent the night of January 15, 1944, but chances are he was also in a festive mood. He’d just had a hand in killing Benny Zuckerman, and that meant a different kind of wide-open horizon. The days of gangster war, when any Scarface wannabe could try shooting his way to the top of Chicago’s rackets, were over, and the days of the looser organized-crime confederation were ending—were ended, in part, by Zuckerman’s murder. It was one more step in the corporatization of crime, one more quasi-independent middle man out of the way, with his operations ripe for the plucking. And Patrick planned to be the one who plucked them. No matter if he was tied all the more

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tightly to Syndicate bosses who told him how high to jump, the money he got for being part of their operation was every bit as good as the stuff Zuckerman had held onto. Pick almost any day between those two dates, and there’s a good chance that Jacob Arvey was shaking hands with someone. More than anyone else in Jewish Chicago, it fell to him to negotiate the political sea change from the crude saloonstyle politicking of Manny Abrahams in the Carter Harrison era, through the gangster-riddled days of Morris Eller and Big Bill Thompson, to the efficient Machine politics of the middle 1940s. He was a force in bringing about that change and a pillar of the new system once it established itself with the election of Anton Cermak in 1931. He came to personal power in a ward where it was often difficult to distinguish the politicians from the gangsters, and he could never entirely free his political apparatus from connections to organized crime. At the same time, though, he found a space between the corruption that preceded him and the impossible-to-achieve purity that reformers from outside his world clamored for. Arvey established that middle ground between crime and reform by building relationships, by shaking hands everywhere he went. Some of those hands were relatively clean, and he’s generally credited with making it possible for Illinois to elect Paul Douglas, one of its most progressive US senators,4 for boosting Adlai Stevenson II to Illinois governor and then twice to the Democratic presidential nomination,5 and for helping engineer Harry Truman’s razor-thin presidential victory in 1948.6 Others of those hands were dirty enough that he couldn’t entirely remove the stain they left behind, but he never let that stop him. When he died, the Chicago Tribune, a staunchly Republican newspaper that had long crusaded against him and his organization, pronounced him ultimately good for the city. Noting his “record was free of scandal” despite his willingness to “tolerate crooked colleagues,” the editorial board declared, “There have been far worse forms of backroom politics than those practiced under Mr. Arvey. In general, he served his party well—and in doing so, he served the city well.”7

II Arvey made no apologies for the way he went about things. “It was what is called a machine. Machine politics,” he told an interviewer in 1977. “I am not ashamed of it. There is only one meaning to machine: a disciplined organization. Strong enough to discipline its members.”8 He meant “discipline” in the positive sense

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that everyone in the organization was on the same page, doing his or her piece of the collective work in a way that represented the same goals and the same tone. Yet there’s an edge to that word. You don’t have to read Michel Foucault to associate discipline with punishment, with breaking the law, and Arvey’s use of the term was a partial admission that he and his organization weren’t above the occasional bit of election fraud, insider dealing, or even menace. As he acknowledged of his precinct captains in a later interview, “Some of them went to illegal means to do it. I know it. I regret it very much, but they were inconsequential in relation to the ultimate result.”9 Arvey grew up in that system as, in many respects, a child prodigy. After losing his father in an accident when he was only thirteen years old, he went to high school and then, skipping college, went straight to John Marshall Law School.10 He entered politics almost immediately, becoming an assistant state’s attorney for Cook County in 1918 when he was only twenty-three.11 He was energetic and capable even then, and he seemed the perfect fit to serve as the public face of an organization that depended on “illegal means” every now and then. In 1923 he was selected the 24th Ward organization’s aldermanic candidate, which was, for all intents and purposes, the same thing as being appointed to the position. When Democratic reformer Michael Dever was elected mayor in the same election—providing a four-year interruption between Thompson’s second and third terms—he chose Arvey as his floor leader, a remarkable and quick rise in a context that usually took years of establishing relationships. At the same time as he rose so quickly, Arvey showed clear patience. Publicly at least, he deferred to the official leaders of the 24th Ward, Michael and Moe Rosenberg, and he kept a surprisingly low profile. He may have matured in a system that made a great deal of the various ward bosses, but he didn’t seem in a hurry to claim such a mantle for himself. As the Tribune put it, “It was characteristic of Jake Arvey that the organization was never known as the ‘Arvey machine.’ His manner was low-key; he preferred to be a power behind the throne in City Hall.”12 Instead, he seemed prepared to learn as much as he could from his predecessors and then avoid the mistakes they made. The Rosenberg brothers had no such scruples and made their share of mistakes. Early Jewish settlers in Lawndale, they established a successful scrap metal business through connections to Samuel Insull, a protégé of Thomas Edison and the architect of Chicago’s lucrative utilities industry. Insull used them, as Moe put it in later testimony, to maintain “a friendly attitude between the different aldermen and politicians for the companies.”13 That translated to old-fashioned graft with

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the alteration that the politicians got paid off not in cash but in the opportunity to buy stock or real estate at below-market prices. It meant as well that the brothers needed to be in politics for their personal—and for Insull’s—gain. In fact, according to at least one report, a redistricting that took effect in 1923 reshaped the 24th Ward so it would be “cut out with a design of making [Michael] Rosenberg its leader.”14 With Insull’s financial connections and support from across the city, the Rosenbergs oversaw the creation of the 24th Ward organization just as the Jewish population of Lawndale became aware of its political strength. Despite the money behind them, the Rosenbergs ran into bad luck. Michael died suddenly in 1928 at age forty-one. He’d been the senior partner, the one who’d served an apprenticeship as an alderman and eventually as a Metropolitan Sanitary District trustee alongside Morris Eller. Moe succeeded him, but he had already spent nearly two years in jail on an interstate commerce violation,15 and he reportedly had to plead with Insull to retain his brother’s business connections.16 Moe may have been less capable than Michael, or he may have run into the misfortune of the Depression, but he could not keep things running smoothly. He was charged in 1934 with tax evasion, and he found that much of the Insull money had evaporated in a series of complicated paper transactions. If he hadn’t died of an embolism right before his trial, he would almost certainly have gone back to jail. He was only forty-four. His estate, once valued at over $2 million, was down to $15,000.17 It’s easy to imagine the lessons Arvey took from Moe’s funeral. On the one hand, it drew more than 5,000 mourners and featured eulogies in Yiddish and English that suggested the government had gone after him, in part, out of “prejudice.”18 On the other hand, many of Moe’s former political associates had to deny he’d bribed them, and several erstwhile friends claimed they didn’t really know him at all.19 In other words, it showed both the potential for tapping into the strong sense of Jewish communal identity but also the risks of flying too high on graft and speculation. It seemed to point the way forward through moderation, through balancing the riskier elements of the organization with the more dependable loyalty—though labor intensive in its cultivation—of the everyday voters, the ones who turned out in such dramatic numbers to mourn a felon facing a second set of charges. Either way, the Rosenbergs’ early deaths left a still surprisingly young Arvey as the undisputed head of the 24th Ward by the early 1930s. In perhaps the same way, Arvey managed eventually to subsume the remnants of Morris Eller’s 20th Ward organization. Arvey’s early years in the City Council coincided with Eller’s peak power, and with Eller, a Republican in a city governed

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for much of that time by Big Bill Thompson, he often had the upper hand. Still, the 20th and 24th Wards had the two highest concentrations of Jews in the city, so Eller and the 24th Ward organization had incentive to collaborate. Michael Rosenberg and Eller had at least occasional cross-party arrangements where each would support the other’s candidates.20 It may be telling as well that Eller was a pallbearer for Michael in 1928.21 Eller’s organization collapsed under the same excesses that did in the Rosenbergs a trap that Arvey always seemed to avoid. Eller won his reelection campaign in 1928 after his sluggers murdered Octavius Granady. Even so, he faced twenty-three counts and a list of 576 potential witnesses in a lengthy trial that eventually bled his organization.22 He had his toughs extorting organized crime figures across the city to raise funds for his defense, and one of them, Benny Zion, was murdered for his efforts.23 He assigned other sluggers to intimidate prosecution witnesses; in one case, a woman reported she’d been told “you are going to be bumped off just as sure as there is a God.”24 In the end, despite denunciations from President Herbert Hoover25 and a prosecution featuring the head of the Crime Commission, he, his son the judge, and seventeen others were found not guilty.26 It was, though, a pyrrhic victory. Eller’s trial was costly, but he really lost his power because the larger political context was changing. At a citywide level, naked gangster politicking was out. Capone’s contribution of as much as $260,000 to Thompson’s 1927 reelection campaign27 was only one instance of the ways that Thompson was publicly beholden to organized crime, and the city simply wasn’t having it any more. Within the Jewish community the movement from Maxwell Street to Lawndale was far enough along that the community’s center of gravity had shifted. Lawndale had the greater pull, and Eller’s fall was an extension and further cause of that reconfiguration. Some of Eller’s political operatives moved west—among them Samuel Epstein, who’d been Eller’s chief election engineer,28 and Sidney Deutsch who would go from Eller protégé to Arvey’s eventual candidate for Cook County Board president.29 So did some of his expert sluggers who found Putty Anixter and Davey Miller’s places just as accommodating as Maxwell Street’s Block’s and Larman’s had been. And Arvey was there to greet them, all of them, as they found their way to burgeoning Lawndale. In something of a parallel to the way organized crime adapted to the confederation model in the wake of the St. Valentine’s Day Massacre, Chicago politics moved from naked corruption to the more complex balance of power that the Democratic machine facilitated. Eller and the Rosenbergs faded— more or less taking the Miller brothers with them—just as the tommy-gun politics

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of the Prohibition era faded, because the Democratic machine that emerged in the early 1930s represented a better and more sustainable model for drawing votes and distributing spoils. With the election of Anton Cermak as mayor in 1931, a campaign that Arvey and Moe Rosenberg supported, the rules changed. There was still room for sluggers—Benny Zuckerman was still doing very well for himself—but it was time to play it more quietly. It was time to let the politicians distance themselves from the organized crime that had been so central in the era that was ending.

III In one way of thinking about it, Arvey chambered the bullets that killed Zuckerman when he left for the army in 1940. His departure wasn’t permanent—he’d come back and, for a time, hold even more power than before—but it upended the balance between the legitimate and criminal enterprises he’d established in the ward. Zuckerman thought himself the natural successor, and it’s likely there were others who felt their time devising policy, knocking on doors, and even knocking on heads warranted the promotion for them as well.30 The one who emerged on top, though, was Arthur X. Elrod. And, while Elrod looked like a politician in Arvey’s mold, he turned out to have more—and more direct—ties to the Syndicate. Lenny Patrick represented the gangster face of the increasingly corporate Outfit that would take Zuckerman out. Elrod was the political face of the same phenomenon. Maybe if Arvey had been there, things would have turned out differently. Arvey certainly had his ties to organized crime. He was, for instance, a close friend of Jake Factor, the con man whom Syndicate boss Murray Humphreys used in 1933 to frame rival Roger Touhy for kidnapping—a conviction overturned twenty-six years later—thus clearing the Far North Side for Syndicate expansion.31 Also in 1933 police found Arvey’s private phone number in the address book of murdered gangster Ted Newberry.32 In 1934 it came out that a representative from a Syndicate-backed laundry association—in effect a racket—used Arvey’s campaign office to threaten a dry cleaning owner who wouldn’t join.33 And, in 1946 independent gambling operator James Ragen testified that Arvey intervened with the Syndicate to permit Zuckerman’s old partner Louis Dann—sole survivor of the four bosses of Lawndale crime—to return from hiding in Los Angeles.34 Perhaps most damning, in 1947 he was linked through one of his precinct captains to the

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controversial paroles that went to Syndicate leaders Paul Ricca, Tony Campagna, Phil D’Andrea, and Charles Gioe, a move that drew condemnation from law enforcement officials across the country.35 That’s a long list, but each item was circumstantial, suggestive of a connection to the Syndicate without proof of one. Elrod’s ties were more direct. If Arvey walked a fine line between outright corruption and true reform, Elrod fell squarely on the shady side. As a young man, he was associated with Jack Zuta, a notorious pimp and gang leader who eventually allied with Bugs Moran and the remnants of the North Side Gang after the St. Valentine’s Day Massacre. He seems to have been fairly removed from the business of prostitution itself—Zuta transferred title to a couple properties so Elrod could stand as bail bondsman—but the connection would likely have tarnished his political prospects if it had been more widely known.36 Probably through his organized-crime connections, he became assistant manager for the city corporation counsel’s office, where he answered to a longtime go-between for Mayor Thompson and the Capone gang, Samuel Ettelson.37 In 1929 Elrod was fired after it was discovered he was working a second job as treasurer of Acme Sales, a company specializing in the manufacture of slot machines, punch boards, and other equipment for gambling. Compounding that no-show job performance, he allegedly urged a complicit police officer to shoot a printing company representative who was trying to collect on a past-due bill from Acme.38 Elrod became secretary to Arvey in 1933,39 but it’s likely his gangster connections were part of what made him a good fit for the job. He was, for instance, tied to the election violence of Morris Eller during the investigations around the murder of Octavius Granady. Detectives discovered a plot to raise funds for the defense of James “the Mad Bomber” Belcastro, a Syndicate tough who was on trial as one of Eller’s election-day terrorists. The idea was to levy “assessments” against gambling joints, with Al Capone, Davey Miller, and Putty Anixter’s partner William Skidmore all expected to send cash in care of Zuckerman’s partner Ben Glazier. As they followed the trail of the money, detectives discovered the phone number for one of the meeting places was registered in Elrod’s name.40 The details are lost, but it’s not hard to imagine he brought such a capacity for organizing criminals to his work in the 24th Ward headquarters. In at least a handful of instances, it was worse than simple financial crime. When James Ragen was murdered in 1946 by Lenny Patrick, David Yaras, and William Block, detectives reportedly produced (and later lost) a wiretap recording of Block talking to Elrod at the Covenant Club. A police commissioner testified in court that Elrod indicated he was “with them [the gamblers] when they’re cold and

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he can’t leave them when they’re hot.”41 The translation seemed to be that Elrod was assuring Block he wasn’t going to drop the men once they’d become suspects in the high-profile murder. Even more, the message seemed to be a pledge that he was willing to put himself forward as an accessory after the fact for murder. Elrod was never charged in the crime, but the implication is still staggering; he could blandly talk about being involved in one of Chicago’s highest-profile killings. Elrod’s corruption and organized-crime links became a national story in 1951, when muckraking journalist Drew Pearson dedicated two of his syndicated columns to Elrod’s crooked rise. He offered details about Elrod’s campaign donors, hoodlum supporters, Democratic political ties, and personal income. He presented Elrod as exemplifying the corrupt nexus of Democratic politics, describing him as someone allied to valuable causes but doing more harm than good in the way he provided gangsters a foothold in the party. As he put it, “In Chicago, part of the support for Democrats comes from Artie Elrod. His support in turn comes from the hoodlums. He has been so successful politically and otherwise, that in a few short years he has parlayed his income up to $50,000 a year, tho [sic] his visible means of support is chiefly from the modest salary paid him by Cook County.”42 Pearson’s column appeared in dozens of papers across the country, making Elrod briefly a latter-day Capone, insofar as he served as the personification of the corruption and violence bedeviling what Pearson called “the sprawling, lucrative, gangster-infested area known as Cook County.”43 Elrod wound up with much of the blame for the gangster violence that erupted in the middle 1940s, climaxing in Zuckerman’s murder. In 1945, for instance, unidentified police officials told the Tribune that Elrod had fumbled the delicate balance Arvey established among would-be gambling bosses and created competition that meant violence and out-in-the-open corruption. As the paper put it, “Out in the Fillmore district police and precinct captains declared that Arthur X. Elrod, Democratic committeeman of the 24th Ward, which goes Democratic by a 25 to 1 vote, had lost control and couldn’t be held responsible for the many ‘sneak’ gambling dives that recently had opened.”44 And in 1948 investigators from the Crime Commission were at least considering the possibility that Zuckerman and his partners were murdered less because of gambling profits than to secure Elrod’s power in the ward.45 Elrod’s role as 24th Ward power broker may have climaxed in 1945, though, when he had to decide what to do about Willie Tarsch. With Arvey gone and Zuckerman murdered, Elrod was clearly the power in the ward. Tarsch was the last of Zuckerman’s partners still trying to make a go of it at the R&K Restaurant.

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The Syndicate had supposedly found Zuckerman tough to work with in his refusal to kick back enough of the cut and his insistence that he was an independent figure in a town increasingly in thrall to the corporate Syndicate. Tarsch was still trying to play by the old rules, still trying to operate as if, having lifted the gambling concession from Zuckerman’s dead hands, it was his to do with as he wanted. A handful of unidentified gangsters joined Elrod for dinner at the Chez Paree Restaurant, a place he was reported to have a “piece of ” alongside assorted other organized crime figures. The Syndicate gangsters apparently complained about Tarsch, rehearsing arguments they’d been making for weeks. Elrod seemed inclined to find a way to save the old independent gangster, perhaps because he saw a reflection of his own situation as someone squeezed from full control of his turf. Still, he recognized frustration when he saw it. He resisted for a time, tried to find a compromise that would solve things without bloodshed. His imagination failed him, though, and he finally threw his hands in the air. “Take care of it in your own way,” he allegedly said.46 At that, the last independent Jewish gangster in Chicago, Benny Zuckerman’s junior partner and heir, was as good as a dead man.

IV Put differently, Benny Zuckerman got to the top of the Chicago Jewish gangster world by climbing the edifice that Davey Miller and Putty Anixter built. In similar fashion Arvey reached the pinnacle of Chicago Jewish politics by weaving the Eller and Rosenberg operations into a coalition that balanced progressives with the gangsters that Elrod came increasingly to represent. At his peak Arvey helped engineer national politics and, within the city, played a key role in bringing forward Richard J. Daley as mayor, a move that reshaped city politics for more than a quarter century. Arvey remained prominent even then, exercising his slowly diminishing influence in an era of slow but dramatic political transformation. When Zuckerman was displaced by Lenny Patrick, the Outfit—as the Syndicate came to be known in its most corporate form—took over. Arvey was still very much part of the scene, but Chicago corruption had become far more subtle and complicated, and that meant he could keep his hands clean while business proceeded as usual. That change, marking the end of the independent Jewish gangster, was equal parts criminal and political. It marked a transition not simply from one type of organized crime to another, but in the very ways in which organized crime and

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politics would interact. The gangsters consulted Elrod before they fired their bullets in 1945. A generation earlier, the politicians often were gangsters, as in the cases of Eller and Manny Abrahams, so they did their own slugging and shooting. A generation later, in the mature machine that Arvey set his life toward building, the space between politicians and gangsters would widen to the point that a Lenny Patrick would have almost no direct political contacts. That work would fall to a slice of the gangster elite, in the end to Patrick’s mentor, Gus Alex. With Elrod’s blessing, then, Tarsch went out like Zuckerman, like a Scarface kosher Capone. It was no Scarface end for Elrod, though, who died of a heart attack in his bed on July 22, 1959, when he was only fifty-eight. At the time of his death, he remained a citywide power broker as a member of the Cook County Board of Commissioners, and his obituary referred to him, still, as a protégé of Arvey.47 By that time, Elrod lived on the North Side in Lakeview, having followed many of the Lawndale residents in that general direction. Whether and in what ways he remained connected to Lenny Patrick isn’t clear,48 but the traces of their connection are. When Tarsch was gone, when the last remnant of Zuckerman’s organization was eliminated, Elrod was in position to establish a new normal in the final years of Jewish Lawndale. That meant recognizing Patrick and his partner David Yaras as the new bosses of west-side gambling. It meant accommodating to the demands of a Syndicate that had swallowed yet more of the city. Arvey may have had a hand in that transition; he was certainly aware of it. But the Syndicate’s corporate takeover of the independent Jewish gangster took place on Elrod’s watch, and he’s the politician who most clearly gave it cover. The young Arvey emerged in the political world of Big Bill Thompson, Al Capone, and Morris Eller. The older Arvey and Elrod were part of a political system that changed parallel to, but separate from organized crime. Each grew more corporate, more citywide. Several eras came to an end when Benny Zuckerman was shot. Several began as well, including the era of the Democratic machine with its more complicated relationship to organized crime. And that era would last as long as Lenny Patrick himself.

Benjamin “Zukie the Bookie” Zuckerman dressed in racketeer fashion in an undated photo first made public after his murder on January 14, 1944. (Courtesy of Sun-Times Media.)

Lenny Patrick stares down a photographer as he strides out of a courtroom in 1955. (Courtesy of Sun-Times Media.)

An unidentified woman looks out the window at blood stains from Zuckerman’s murder in front of his fashionable home at 4042 Wilcox. (Courtesy of SunTimes Media.)

Davey Miller grins from a box at the race track, circa 1922. (Author’s personal collection.)

The Miller brothers, Hirschie (left), Max, and Davey, doff their hats for a candid photo from sometime in the early 1920s. (Author’s personal collection.)

Uncharacteristically fashionable in this 1946 photo, Jack Guzik gives no indication of the more than three decades he had spent building the Chicago Outfit. (Courtesy of Sun-Times Media.)

Manny Abrahams’s saloon stood as a Maxwell Street landmark and served as the headquarters for Abrahams’s rise to power in what would become the 20th Ward. Pictured in front is Abrahams’s brother Morris. (Courtesy of David Abrahams.)

Inside Abrahams’s saloon. Mustachioed Manny Abrahams stands behind the bar with his brother Morris in front of him. Unidentified “boys” sit arrayed in the common area. (Courtesy of David Abrahams.)

Mild-looking Morris Eller showed it was possible to flex muscle on the street as well as through his role in 20th Ward politics. (Chicago History Museum.)

The political powers of Jewish Lawndale—Jacob Arvey (left), Abraham Marovitz, and Arthur Elrod—clasp hands in November 1952 as they face the prospect of dealing with a Chicago Outfit powerful enough to have gotten away with killing Benny Zuckerman and Willie Tarsch. (Courtesy of Sun-Times Media.)

Mugshots of David Yaras taken after a 1952 arrest in Miami, where he spent much of his time after he and Lenny Patrick emerged as the heads of Jewish organized crime in Chicago.

Gus Alex leaning on a cane as he emphasizes his feebleness as part of his defense in 1992. (Courtesy of Sun-Times Media.)

Lenny Patrick in 1992 as he readied for his performance as the central figure in the trial of Gus Alex. (Courtesy of Sun-Times Media.)

James Ragen, a month before being shot in ambush by Lenny Patrick, David Yaras, and Willie Block on June 24, 1946, seems to sense he’s a target as he sits awkwardly after a meeting with the state’s attorney’s office. (Courtesy of Sun-Times Media.)

William Drury, shown here in 1948 after being forced off the police force, remained committed to investigating Outfit influence in Chicago and across the country even at the price of his life. (Courtesy of Sun-Times Media.)

The Maxwell Street produce market as it appeared on May 21, 1939. Note the wheels on the carts that made it possible for the politicians behind the Market—such as Morris Eller throughout the 1920s—to demand kickbacks from vendors who wanted the most desirable locations. (Courtesy of Sun-Times Media.)

Harry Guzik, perhaps the original “Greasy Thumb” of the gang that Johnny Torrio and Al Capone came to run, as he appeared in court on vagrancy charges in 1946. (Courtesy of Sun-Times Media.)

8 SYNDICATE HAMMER

I On April 4, 1932, nineteen-year-old Lenny Patrick decided on his first murder. He didn’t like Herman Glick, didn’t like the way the older guy had shoved him around at a poolroom several days before. Young as he was, Patrick thought of himself as tough. A few years earlier, when he was only fifteen, he’d begun running a sidewalk craps game for the cabdrivers who waited for fares in front of Davey Miller’s restaurant in the heart of Jewish Lawndale. More recently, he’d gotten a gun, and he’d used it, going so far as to hold up a local handbook operation. The result was a year’s probation, and it seemed a step up the ladder toward becoming a full-fledged hoodlum.1 But the twenty-one-year-old Glick was even further along, already hardboiled enough to run with a gang that had murdered a night watchman,2 already with a reputation that gave Patrick the sense that only one of them could walk away from their conflict.3 He was going to find Glick, and he was going to end it. Patrick came from a violent family in a violent world, so in a way he’d been schooled to go for the jugular. He was six when his mother died in the flu epidemic following the return of soldiers from World War I, and his father sent him to an orphanage for the next four years.4 One of his uncles, Meyer Mackenberg, was a Maxwell Street slugger arrested in 1928 along with sixteen others in the wake of the Eller gang’s murder of Octavius Granady.5 Around the same time, his older brother Charles was killed by police at a south-side whorehouse. The police claimed Charles had come to rob the place; Patrick’s father insisted the gun was planted and that Charles was there on the comparatively innocent business of demanding that the management pay to treat the venereal disease he’d picked up

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on an earlier visit.6 Then, later in 1932, Patrick’s father shot his older brother Jack when Jack defended Patrick in an argument. Jack, it turned out, was wanted for a 1931 bank robbery as well as a more recent attempted armed robbery.7 So, when he saw Glick walking near the Sawyer Avenue Synagogue,8 Patrick knew what to do. He jumped out from where he’d been hiding, ran up behind Glick, pulled out his pistol, and fired. Then he ran away before he could see the result. Years later, he tried to justify the assassination as self-defense. “If it wasn’t me—if it wasn’t him—it would have been me,” he said.9 As it happened, Patrick’s aim was off enough that he hit Glick in the neck rather than the head. Glick survived two days and identified Patrick, who was arrested and charged with the murder. Under the laws of the time, Glick’s deathbed testimony couldn’t be used in court, however, and prosecutors couldn’t gather corroborating evidence. They eventually dropped the charges. Patrick did spend a month in county jail, however, and that proved a different sort of school. While there, he cemented his ties to Danny McGeoghegan, a south-side bootlegger with the notoriety to make number thirteen on the Chicago Police Department’s public-enemies list that winter.10 McGeoghegan had some experience in bank robbery—he’d beaten the charges in a $60,000 take in Clearing, Indiana, a year and a half earlier11—and he was putting a new gang together. Patrick joined up, recruited his brother Jack, and set off, bandit-style, for Indiana. In its way, this was a bid to join the larger, confederated gangster world. A score with someone who had ties to the Syndicate—as McGeoghegan apparently once did—could mean an in with the big shots, a chance to curry favor with the sorts who granted the “concessions” that meant a steady income. The result was a fiasco, though. The gang made off with only $12,646.50 from a Culver, Indiana, bank, and they didn’t get far. As city kids they were lost in rural America. McGeoghegan and three others were arrested by a group of vigilantes after they got caught in a thicket of trees.12 The Patrick brothers, who’d split from the rest, were picked up by a similar posse when they flagged down a car as hitchhikers.13 Whatever connections McGeoghegan had were either spent or exaggerated, and Patrick was sentenced to ten years in prison in May 1933. He would not get out until March 11, 1940.14 During that same period in greater Jewish Lawndale, the remnants of the Big Bill Thompson way of business would fade—the Rosenberg brothers would die, Morris Eller would lose his clout, and Davey Miller would sell his restaurant— while the new order of Jacob Arvey, Arthur Elrod, and Benny Zuckerman would rise with the developing Democratic machine and the ever more corporate–style

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Syndicate. Those were big changes in Patrick’s childhood neighborhood,15 but for him it meant seven years of pacing a cell and dreaming of getting things right when he got a second chance. He was nineteen years old, a murderer and a convicted thief. He’d made himself as hard as he needed to be. When he got out, he was going to start his climb.

II It looks as if Lenny Patrick had to borrow a pen on February 25, 1941, less than a year after he was released from jail, when he filled out his application for a social security number. His printing is blunt and blotchy, and the words are weirdly spaced across the page. You can see the man who wrote it wasn’t at home with words on paper, and it becomes almost understandable how a reformatory psychologist could label him in 1933 as a “high-grade moron” with an IQ of 72.3 and a mental age of eleven years and seven months.16 Still, two things stand out in his favor. One, the signature for his first name appears neat and practiced; the “Patrick” looks a little childish, but “Leonard” comes through. It’s as if he wasn’t sure about the family he was born into but was confident about himself. Two, he had a job. He worked at the R&K Restaurant at 3216 W. Roosevelt Road. In other words, Lenny Patrick got out of jail and went to work for Benny Zuckerman. He was, the FBI determined later, a “dice dealer”17 probably overseeing one of the craps game in the upstairs rooms that Davey Miller built to celebrate Thompson’s first mayoral election. Fifteen years earlier Patrick had run such a game on the sidewalk out front. Now he was inside, literally as well as metaphorically. As someone charged with keeping the money flowing, as someone who saw Zuckerman, Ben Glazier, Louis Dann, and Willie Tarsch virtually every day, he had a shot at a different kind of criminal education. These were the guys with the political connections and the Syndicate confederation. These were the guys he could watch and learn from. All sorts of people came and went at the R&K. A Chicago Crime Commission confidential report from May 1944 gives a long list of Zuckerman associates spotted over a several-week period.18 Several were police characters like “Mashie” Huff, “Jew” Ryan, “Cockeye” Nusbaum, “Blackie” Frankie Mauriello, and disbarred policeman Francis O’Malley, all of whom lived above the restaurant or had no other addresses the investigator could determine. Others were citywide gang players like Mike Fitzel and Joey Jacobson, who owned the ritzy Chez Paree

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restaurant, “Dago” Lawrence Mangano who purportedly ran gambling in the area just east of Lawndale,19 or “Chew Tobacco” Frank Ryan who, on the front lines of Syndicate gambling in the Loop, once said he’d been raided 400 times in his thirty-year career.20 A couple on the list were even Syndicate leaders, including “Loud Mouth” Hymie Levin, longtime gambling boss of the 1st Ward,21 and Rocco Fischetti, often identified as a cousin of Al Capone. Not on the list, but regular attendees according to Patrick himself, were Sam Giancana, Milwaukee Phil Alderisio, and Paul Ricca, all eventually regarded at some time as operating bosses of the Syndicate.22 Patrick was just another guy in that crowd, but he was also an ex-con who’d shown he was tough enough to get away with murder and then do a lengthy prison sentence. There’s no way to know whom he talked with, whom he brushed up against, or whom he struck up private friendships with. It’s easy to imagine he befriended some of those people as he went about his more or less menial work. It’s easy to imagine him, still pacing, looking angry or sullen at the money heading to Zuckerman and his partners, the engineers of the gravy train in Jewish Chicago. Then someone in that crowd wanted Zuckerman gone. That someone calculated that, with the recalcitrant old slugger out of the way, more pliable leadership would step into place. That someone recognized the look in Patrick’s eyes, saw him as a hammer the Syndicate could use to break up the bosses who ran the operation Putty Anixter had put together. It isn’t certain Patrick was part of the hit team that took Zuckerman out that night on January 14, 1944, but it is likely. He emerged as a chief suspect over the next few years, and he’s the obvious candidate in retrospect, but he never confessed to the murder and, when he did finally testify, he spoke respectfully of “Mr. Zuckerman.”23 It is certain he had a hand in killing Willie Tarsch, since he eventually confessed to it. Tarsch, the equally unyielding independent, took over briefly once Zuckerman was shot and Ben Glazier dead of his heart attack. Patrick said he’d never gotten along with Tarsch, that Tarsch had asked him to use phony dice in the craps game he ran and had fired his brother Mike for no reason but enmity with the Patrick family.24 First they supposedly cleared it with Arthur Elrod.25 Then they went to work. It was simple, as Patrick described it. He tapped Eddie Murphy, an old friend from his bank robbing days, and a recent acquaintance, David Yaras,26 who’d worked as a driver for Syndicate macher Jack Guzik. He served as lookout while Yaras used a shotgun. With that, Tarsch was gone, and Patrick had the “concession” Zuckerman had once boasted of. He found his way into the Syndicate’s

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federation just as it was tightening into a more corporate top-down structure. When a prosecuting attorney asked him years later about his “main line of work beginning after the death of Willie [Tarsch],” Patrick replied, “It was taking care of the gambling places.”27 It took seven years in prison and four years of schlepping around Zuckerman’s place. Then it took just a couple nights of bold work. He was somebody, and people knew it. After that, the murders came pretty regularly. He admitted to killing Harry Krotish, a gambling rival, in 1948;28 Eddie Murphy, the partner in the Tarsch murder who turned on him, in 1950;29 Davey Zatz, another gambling rival, in 1952; and Milton Glickman, yet another gambling rival, in 1953. But those were just the murders he eventually confessed to. He denied or never addressed others that had his fingerprints on them. He admitted, for instance, to intimidating 31st Ward Republican committeeman-candidate Charles Gross as a favor for Syndicate toughs Milwaukee Phil Alderisio and Charlie Nicoletti. When Gross refused to leave the race, he was murdered on February 6, 1952; Patrick was a longtime suspect.30 It was almost the same story a decade later when Patrick allegedly told 24th Ward alderman Ben Lewis to rein in independent gamblers in the suddenly African American Lawndale-area ward. Lewis was tortured and then murdered on February 28, 1963, and Patrick again emerged as a leading suspect.31 And the FBI determined at one point that he was “undoubtedly responsible” for the “demise” of his longtime gambling partner Arthur “Boodie” Cowan, found murdered in the trunk of his car in 1967,32 a charge Patrick denied. But those were only the murders where he had a clear connection. He came increasingly to be regarded as a “torpedo,” a professional hit man sent to take care of business for the Syndicate precisely because he had no such connection. New York’s Murder, Inc., a loose group of mostly Jewish and Italian assassins working throughout the 1930s, set the pattern for the phenomenon where a centralized syndicate would dispatch professional killers to its peripheries, bringing in nonlocals for quick and violent work. As Burton Turkus and Sid Feder described Murder, Inc., “The Brooklyn triggermen were the traveling salesmen of the national crime cartel.”33 Within greater Chicago, and perhaps beyond, Patrick and Yaras came to play such a role for Chicago’s Syndicate. They weren’t the only ones, certainly, but they were part of that corporate structure, specialists set to settle knotted problems.34 They went where they were dispatched by the Syndicate heads they answered to, and they held onto their various gambling, loansharking, extortion, and racketeering operations as their reward.

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Virtually every one of the couple dozen separate FBI reports on Patrick gives the all-caps warning, “SUBJECT SHOULD BE CONSIDERED ARMED & DANGEROUS IN VIEW OF HIS DANGEROUS PROPENSITIES,” but that hides the graphic nature of what it meant to be a Syndicate killer. In an extraordinary bit of wiretapping in 1962, the FBI caught Yaras discussing his work with a group of associates at a safe house in Florida. Future Syndicate head Jackie Cerone and longtime Patrick partner Fiore “Fifi” Buccieri were lamenting missed opportunities to take out a troublesome union official. Yaras complained, “I wish for Christ sake we were hitting him now, right now. We could have hit him the other night when there was just Philly [Alderisio] and him.” Cerone agreed, and Yaras took it further, “Leave it to us. As soon as he walks in the fucking door, boom! We’ll hit him with a fucking ax or something. He won’t get away from us.”35 This wasn’t a personal dispute; Yaras wasn’t out to defend his and Patrick’s personal territories or operations. Instead, it was pathological loyalty to a larger, corporate interest. In that role Patrick and Yaras spent perhaps as long as two decades traveling across the city and maybe even the country, killing people who somehow got in the Syndicate’s way. They were allegedly part of the sustained effort to take control of the African American south-side numbers racket. The FBI got word they may have been the white men who kidnapped Edward P. Jones in May 1946, releasing him only after he supposedly agreed to a $100,000 ransom and gave up control.36 They were tied through ballistics to the killings of a series of south-side Syndicate confederates, including Danny Stanton and Louis Dorman.37 The FBI considered Patrick a suspect in the 1950 murder of Abraham Davidian in Los Angeles.38 And Chicago police detectives even regarded Patrick and Yaras as suspects in the infamous murder of New York kingpin Bugsy Siegel in Las Vegas in 1947.39 The challenge in describing such work in full is that it was designed to be invisible and untraceable. As Turkus, who famously prosecuted Murder, Inc., described the beginning of his investigation, “Neither we nor anyone else dreamed that these men were more than just local aggregations, limited to the areas in which they roamed.”40 There was no way to know how far a pair like Patrick and Yaras might go in pursuit of such assignments, and there was no way to distinguish their handiwork from that of any number of others. When things went according to plan, they were in and out; someone was dead, and they had all the more credit with the Syndicate, but no one else had any reason to suspect their involvement. It would take something going wrong, something that didn’t follow their plans, to get a glimpse at their methods and their larger place in the Syndicate world. It would take a big screwup.

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III James Ragen liked the confederation model just the way it was. He’d risen from the South Side where, as a longtime figure in various Irish gangs that gradually made their peace with the Torrio-, Capone-, and Nitti-led Syndicate, he’d emerged as the partner and then successor of publishing magnate Moses Annenberg in the Continental Press. While legal in its own right, the Continental was essential for illegal gambling; any handbook that dealt in sports betting, particularly horse racing, needed the instant reporting it had a monopoly over. The Syndicate had never controlled the service directly. Instead, it had always licensed it from Annenberg or his predecessors. By the middle 1940s Ragen had a healthy income and a solid, independent foothold in Chicago organized crime.41 But when Outfit bosses Paul Ricca, Tony Accardo, Murray Humphreys, and Jack Guzik decided they wanted more control and more profits, something had to give.42 First they sent Hymie Levin and a rising wise guy named Gus Alex with a proposition to buy a controlling interest.43 When Ragen declined, they sent Lenny Patrick and David Yaras with guns. On June 24, 1946, Patrick, Yaras, and a new partner, Willie Block, ambushed Ragen on the South Side near the intersection of State and Pershing. They hid behind crates of oranges and other produce inside a tarpaulin-covered truck they had stolen for the occasion,44 and when Ragen’s car stopped for a traffic light, they unloaded with their shotguns. They wounded both of Ragen’s bodyguards— Ragen had been cautious since an assassination attempt two months earlier—and got Ragen himself so brutally that they nearly ripped his arm off. One of the bodyguards managed to start the car and speed away from the intersection, escaping from what would likely have been the final kill. Patrick and his crew had to drive in the opposite direction to make their getaway.45 We know this was a Patrick-Yaras hit for two reasons. First, Ragen survived. He was in shock from the loss of blood and it looked as if he would lose his arm, but his men had gotten him to Michael Reese Hospital in time, and he was recovering. Worse for the would-be killers, he knew it was a Syndicate job, and that knowledge drove him to release a ninety-eight-page statement he’d written earlier about his involvement in Chicago organized crime going back to the early 1910s. Second, three eyewitnesses recognized Block, and that eventually led to identifying Patrick and Yaras as well. Syndicate toughs were usually untouchable in 1940s Chicago; they might get harassed by cops on the street or brought in for the occasional booking in front of newspaper photographers, but real investigation almost

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always got sidetracked. In this case, though, Chicago Police Lieutenant William Drury arrested Block, and his superior, Captain Thomas Connelly, supported him. Block, Patrick, and Yaras would all be indicted in March 1947.46 All that meant a hefty cleanup for the Syndicate. To start, they had to stop Ragen from saying any more than he already had. Stabbing or shooting the man while he was in his hospital bed would have been over the top—and would certainly have drawn even more attention to the already front-page story. So, more slyly, they managed to inject the semiconscious patient with a fatal dose of mercury. The hospital, defending itself from a potential lawsuit by Ragen’s heirs, claimed the toxin was in his system as a result of a “mercury balloon” treatment that should not have harmed him.47 Almost everyone else assumed it was the Syndicate as, indeed, eventual boss Sam Giancana reportedly confirmed.48 Either way, Ragen was finished talking. After that, they had to do something about the witnesses. From one direction, they pulled all the political strings they could. With Jacob Arvey the right-hand man to Mayor Edward Kelley, that meant a general squelching of the investigation, not so much a dropping of it as a foot-dragging with charges slow to come and assorted records going missing. The Tribune speculated openly about such a deliberate slowdown,49 and the matter became public record when the state’s attorney and his first assistant, himself a candidate for superior court judge, were called on to defend themselves under oath.50 Then, in a bit of legal jujitsu, the Syndicate and its allies arranged to have Drury and Connelly, the policemen who’d spearheaded the investigation, charged with conspiracy. The story went that they had persuaded three otherwise innocent African Americans to coordinate their stories as part of a vendetta against Guzik. Absurd as the move seems in retrospect, it worked. Two of the witnesses recanted their testimony. One of them, John White, was so committed to his change of heart that he accepted jail time, insisting he’d “go to jail rather than let an innocent man suffer.”51 Three months later, he was killed in a brawl, a circumstance suspicious enough to warrant a disclaimer from police.52 Just to be sure, someone stole the only copy of his testimony from his police file, erasing any possibility that he could play a part in the case against Patrick and his partners.53 In similar fashion, one of the affidavits Ragen had supposedly presented to police went missing as well.54 And then, at least according to Drury and Connelly, the police department also lost a wiretap recording that caught Patrick, Yaras, and Block discussing the murder with Arthur Elrod.55 With just one witness

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remaining, the case evaporated. Adding injury to insult, Drury and Connelly were both suspended and then fired from the force. Even with the immediate threat of the trial gone, there was one loose end remaining. Drury and Connelly refused to let go of what they saw as a dangerous miscarriage of justice. Both men accepted work with the Chicago HeraldAmerican where, as part of the Hearst newspaper syndicate, they helped inform Jack Lait and Lee Mortimer, whose series of Chicago Confidential and New York Confidential books would lay the groundwork for the tabloid gangster coverage made famous in James Ellroy’s L.A. Confidential novel and film. Drury in particular raised as much noise as possible about the sinister reach of the Syndicate. He opened a detective agency with the goal of “smash[ing] syndicate gangsters anywhere.”56 He wrote a series of ten lengthy articles for the Miami Daily News which, taken together, provide one of the most substantial exposés of organized crime from the era.57 Rumor had it he even tried to wiretap Syndicate leader Rocco Fischetti’s home.58 Then, in late 1950, word came out that he’d agreed to testify before the Kefauver Senate commission on national crime. On September 25, 1950, just days before Drury was scheduled to talk, Syndicate killers caught up with him as he parked his car in his garage at 1843 W. Addison, a mile west of Wrigley Field. They fired at least four bullets through his windshield, a noise so out of place in that area that neighbors took it for the backfirings of a car and no one knew to check on him for almost an hour.59 The murder, of course, outraged the city, and everyone had a sense of who was responsible. As the Tribune put it in “Why Drury Was Killed,” an editorial lathered with disgust, “There is no real mystery as to why William Drury, the former police lieutenant, was murdered Monday. He was murdered because a verminous gang of panders, killers, and gambling racketeers has been given political protection in Chicago for more than 30 years. Since 1933, the only organization that could extend that protection has been the Democratic machine now run by Jake Arvey.”60 The murder remains officially unsolved even though it marked perhaps the most dramatic moment in the Syndicate’s evolution into the all-encompassing, Outfit. There were a handful of obvious suspects, but investigators could find no incriminating evidence, and despite the public outcry, there was pressure to make the politically charged killing go away. It faded from civic memory but never vanished altogether. Willie Block was so dogged by the charge he was a murderer that he fled to Los Angeles in what he claimed was a bid to start his life over.61 More than forty years later, according to Chicago Crime Commission investigator

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Wayne Johnson, the Chicago Police Intelligence Unit reopened the case and got a hit: during his federal prison sentence, Lenny Patrick had admitted responsibility.62 Patrick was fading then, a man too old and addled to bring into court, so there was nothing more to do. Instead, it was simply evidence of one more time when Patrick had served as the hammer to knock down someone who’d gotten in the Syndicate’s way.

IV Cynical as it sounds, the Syndicate campaign worked. On the corporate front they absorbed Ragen’s wire service as seamlessly as they’d absorbed Zuckerman’s gambling operations. On the legal front they demonstrated the extent to which they could get away with suborning and intimidating police officers. Not only was Drury dead, but his partner Connelly, a onetime police captain, spent most of the rest of his career working as a security guard for a department store.63 In that context it’s hard to imagine how an honest, independent officer could ever find the courage to come forward with what he knew about departmental corruption and organized-crime influence. And, on a notoriety standpoint, they waited out that wave of public concern. The Kefauver Commission offered explosive findings about organized crime across the country, and its exposure of the Fischetti brothers may have rebalanced some of the power of the Chicago Outfit, but it eventually came and went. As for Patrick himself, you couldn’t call it smooth sailing for the next quarter century, but it was close enough. You didn’t get many mistakes when you were part of the Syndicate, but Patrick managed to clean up the botched killing of Ragen and along the way establish himself as a clear and permanent part of the Syndicate. The McClellan Commission would pick up in the late 1950s where Kefauver left off, but in many ways it would be starting from scratch. That pressure led J. Edgar Hoover and the FBI to begin its Top Hoodlum Program, with Patrick one of the suspected leading figures of the Syndicate, but his real harassment wouldn’t pick up until even later than that. There would be raids on his handbooks, nasty articles in the press, and unpleasant notoriety to deal with,64 but those were merely occupational hazards. He would stay on solid ground until, in a vastly changed political and social climate, the sun would start to set on him in 1974.

9 SIZING UP THE OUTFIT

I Anton Cermak saw an opportunity. It was 1931, and he’d achieved his lifelong goal of becoming not just the mayor of Chicago but the political boss as well. Unlike Big Bill Thompson who’d held the office for twelve of the previous sixteen years, he was not beholden to bootlegger or gambling kingpins.1 He’d come to power by yoking strong neighborhood organizations—like his own 12th Ward organization from Bohemian Lawndale and the Jewish 24th Ward where Jacob Arvey was coming to power—so he was less connected to the naked corruption that had obligated his predecessor to depend on organized crime to turn out the vote. He represented a coalition of ethnic Chicagoans standing between the temperance crusaders who created Prohibition and the vicious gangsters who profited from it. The crusaders were in retreat with the return of legal alcohol, and the gangsters were in disarray with the enforcement of income tax laws that had sent Al Capone and several others to jail. If he could further disrupt the Syndicate leadership, Cermak seemed to think, he could push forward a group of gangsters more sympathetic to his interests. He could, that is, take control of organized crime the way no mayor before him ever had. So Cermak took a shot. He established what he called a “Hoodlum Squad” responsible for taking down Capone’s successors, chief among them Frank Nitti. He named as its leaders a pair of Jewish policemen with purported ties to organized crime, Harry Lang and Harry Miller, brother of Davey Miller. He promised to “drive the hoodlums out of business,”2 and he unleashed his police to harass Capone’s onetime followers across the city, arresting them sometimes simply for gathering together.3 Things culminated on December 19, 1932, when Lang and

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Miller burst into Nitti’s office at 221 N. LaSalle with two junior officers in tow. While Miller gathered Nitti’s associates in an outer room, Lang and a partner closed the door to the inner office. Without warning, Lang shot Nitti three times, then shot himself in the arm to make it look as if he’d killed the gang boss in self-defense.4 Cermak did have a plan. The Syndicate of 1931 had taken out most of its leading enemies, but pockets of the disaffected remained. The North Side Gang was more or less erased, but Teddy Newberry, an old O’Banion-Moran loyalist with ties to Jacob Arvey,5 had what Benny Zuckerman would term “the concession” to run the North Side as a Syndicate subordinate after he’d made his separate peace. Further north, the Touhy Gang still clashed with the Syndicate for the right to sell booze and run suburban rackets. If he could get Nitti out of the way, Cermak seemed to figure, he could help the Jewish Newberry and the Irish Touhy rise, and he could depend as well on some of the losers from the increasingly tighter criminal confederation—with Harry Miller perhaps representing other groups, like the Miller brothers, who’d seen their standing sag as the Syndicate consolidated power. That would leave him as the patron of the city’s new crime boss. In the same way he’d used his political coalition to do an end run around the Irish, who dominated ward politics, he could undermine the Italian dominance of organized crime. But Cermak ran into bad luck. Somehow, Nitti survived his wounds. Lang’s junior partner testified the attack had been premeditated, essentially a police assassination attempt, and Lang and Miller were dismissed from the force in disgrace. Newberry’s body turned up in a ditch when he went missing less than a month after the shooting. Then, a little more than a year later, Cermak himself was killed while riding in a motorcade next to president-elect Franklin Delano Roosevelt. Standard history holds that the assassin, Giuseppe Zangara, a onetime marksman from Italy, was aiming for Roosevelt and missed. Many Chicagocentric observers like Judge John Lyle, Crime Commission head Frank Loesch, and Lenny Patrick–chasing policemen William Drury and Thomas Connelly long suggested, however, that Zangara hit exactly the man he was aiming for—that the Syndicate killed the mayor of Chicago in retaliation for the attempt to kill Frank Nitti.6 Cermak’s plan died with him, but the incident helped reshape the relationship between organized crime and Chicago politics for the rest of the twentieth century. Cermak’s successor, Edward Kelly, was notoriously corrupt himself—in fact, Arvey and other machine leaders had him supplanted in 1947 when his tolerance

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of gambling and other gangster crime turned into a clear campaign liability7—but it was a different sort of corruption, closer to the old Carter Harrison approach where crime was tolerated as long as it stayed out of sight.8 Gangster money still made its way into police hands, but it got there less directly, with more plausible deniability. A city scarred by the memory of Al Capone and Big Bill Thompson couldn’t tolerate another gangster mayor even if it wasn’t ready for straightforward honesty. The notorious 1st Ward in particular, evolving only slowly from the control of Hinky Dink Kenna and John Coughlin to the more sinister John D’Arco and Pat Marcy, remained a hotbed of double-dealing and political corruption—newspaper articles testified routinely to the situation—but city government as a whole divested itself of the obvious links to organized crime that Thompson had shown and Cermak had reached for. The Jacob Arvey model prevailed; crime had influence, certainly, but it was mediated by layers of corruption crossed with legitimate public interest. In other words, Cermak’s failure to make himself the direct boss of the Syndicate marked a détente in Chicago politics that eventually resulted in the change from the confederated system of organized crime to the more corporate structure. It wasn’t an overnight change, but Cermak’s death—whether at the long-range hand of the Syndicate or as a fluke of being in the wrong car at the wrong moment— allowed Kelly and his partner, Cook County Democratic Chair Pat Nash, to assemble a machine with deep enough roots in labor and ethnic coalitions that it didn’t need the day-to-day violence of Abrahams, Eller, or Thompson. That meant politicians didn’t have to depend upon gangsters so directly, and it marked, for the most part, the end of the gangster/politician hybrid.9 Similarly, the Syndicate’s departure from that relationship allowed it to assume a lower profile, to become a quiet corporation supplanting the necessarily noisier confederation model—noisier simply because it had more independent operators who might complain or cause trouble if they weren’t satisfied by the overall decisions. It meant a transformation from the world in which Benny Zuckerman had thrived into the one that fostered Lenny Patrick.

II Sometime in the late 1940s Chicagoans started referring occasionally to the Syndicate as the Outfit.10 The name had a nice, anonymous ring to it. Being part of it implied wearing a uniform, an “outfit” you could slide into and lose yourself

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within. Al Capone’s Scarface persona had given one sort of identity to the Syndicate that formed around him. The Outfit brought a kind of hush in its place. It implied an organization both vast and ordinary looking. In the Eisenhower era, when the film The Man in the Gray Flannel Suit and the novel it was based on could critique Americans for depending too much on work to give them identity,11 the concept of the Outfit reflected a similar, criminal sense of corporate control. As with the legitimate American workplace, so with the workplace of organized crime.12 Starting in 1933, when Cermak failed in his bid to subordinate the Syndicate to the mayor’s office, and culminating in 1943 with Frank Nitti’s suicide, the Outfit moved into the shadows, becoming, in much of the popular imagination, a second kind of government invisible to legitimate Chicago. While the question of “Who runs the Capone gang now?”—a sentence that served as the lead for an October 1, 1950, newspaper story—reflected an air of mystery that gave the Outfit some of its power, observers gradually provided answers. The Outfit that grew out of the Syndicate and the Capone gang before that had some familiar names within it and seemed to have a structure mirroring the corporate structure of other institutions of the time. Prominent people would guess wrong, the names would change, and there would never be the fixed structure that many tried to read into it, but the Outfit would eventually come into focus.13 It may have set out to be invisible, to be no more revealing than a gray flannel suit, but time eventually revealed a great deal about just who was holding the hammer that Lenny Patrick had become. For starters, most observers recognize a consistent “chairman” role, and consensus has it that Paul Ricca assumed it after Nitti died.14 In that capacity he served as a kind of elder statesman, making peace between feuding factions when possible, and directing murders to solve problems when not. Ricca encountered a substantial challenge when he was sentenced to ten years in prison for his role in a complicated scheme to extort Hollywood studios through the Outfit’s control of the projectionists’ union. It took four years, untold hundreds of thousands of dollars, and yet another hit on Arvey’s reputation,15 but Ricca’s Syndicate allies used their political connections to get him out six years early. He later served a two-year sentence for tax evasion and long faced deportation, but he fought it off and, in most historians’ eyes, remained the Outfit’s senior figure until he died in 1972, when he was replaced by Tony Accardo. Just beneath that role was “the boss,” more or less the chief operating officer. Most see Accardo as having assumed that position on Nitti’s death and then having held it until roughly 1957, when he made way for the loud Sam Giancana who

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became the eventual top target of both FBI and senate investigators. There followed a succession of such figures—including Sam “Teets” Battaglia, Phil Alderisio, and Joey Aiuppa—most of whom lasted only a few years because of prosecution or death. One later such figure was Sam “Wings” Carlisi, who reputedly became boss around 1989, just in time to become the focus of the investigation that eventually compelled Lenny Patrick to testify against him. It was stressful work, and anyone who assumed the role immediately came under heavy law-enforcement scrutiny. Only Accardo, whom most see as having assumed the chairman role when Ricca died, had particular staying power. There was also a tier of territorial bosses, whom later analysts termed “crew chiefs” or “captains,” each of whom had a cohort of “soldiers” answering to him.16 Most observers put Patrick in such a slot, first on the West Side and later on the North, seeing him as more or less a peer of figures like Ross Prio, Ralph Pierce, and Butch English, though some believed the fact that he was Jewish kept him from full membership.17 Later such figures would include Rocco Infelise and Albert Tocco, contenders to become the boss when they were convicted in trials from the 1990s. As a special part of that category, with a generally higher standing, there was a succession of liaisons in Las Vegas, starting with Johnny Roselli, and moving to Marshall Caifano and Tony Spilotro, best remembered as the model for Joe Pesci’s Nicky Santoro in Casino. And then, finally, as part of a cohort of executive advisors, there was a particular group that specialized in payoffs, that served as the clearinghouse for bribing police and politicians. FBI agent Bill Roemer referred to that group as the fixers or “the Connection Guys.”18 The notion may seem strange at first glance, but such centralization was a crucial part of the corporatization of the Syndicate. With fewer people exposed to the delicate apparatus of corruption, there were fewer opportunities for mistakes or betrayals. Patrick later acknowledged that change in the Syndicate’s business model, testifying that, while aldermen were in control of illegal gambling operations in Lawndale, it was different once he reestablished himself in Rogers Park. “I don’t think it was the aldermen then,” he said. “I didn’t bother with that there then. There was an office that was only there.”19 He was, he implied, going through the centralized structure of the Syndicate, through Gus Alex at that point, rather than, as Zuckerman had done, paying off someone like Elrod directly. In a quirk that Roemer notes, the Connection Guys tended to be non-Italians. For much of the Outfit’s history, the Welsh Murray Humphreys called many of the shots.20 He’d begun his career as a racketeer and earned notoriety for his role in

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framing Syndicate opponent Roger Touhy for kidnapping,21 but, as Roemer suggested, he was acknowledged above all for his role in corrupting public officials until he died of a heart attack in 1965.22 In eerily corporate fashion, newspapers announced his successor as if the Outfit had sent out a press release touting its new CFO. “Gus ‘Slim’ Alex, 50, the crime syndicate’s Loop gambling boss and an influential figure in Teamster union activities here, has been chosen to succeed Murray ‘the Camel’ Humphreys as the mob’s political fixer.”23 Alex was Greek, yet that did not prevent him from becoming one of the two or three most important figures in the Outfit that Patrick dealt with in his final years. The first of those Connection Guys, though, the one who set the template that the others followed, was the Jewish Jack Guzik. As far back as the Johnny Torrio days, Guzik specialized in political corruption. In 1922 his older brother Harry and sister-in-law Alma were sentenced to a year for prostitution—they had, according to multiple sources, kidnapped a country girl and forced her to turn tricks in a house they ran.24 Harry’s other role within the gang, at least according to one report, “was serving as downtown ‘payoff ’ man for Torrio.” The system was so well established that Harry “had an office in the loop, where he paid Torrio money to police officials who were protecting the vice king.”25 It’s likely Jack Guzik was already part of that mechanism, and it’s even possible he was the Guzik doing most of such work; as it was, the brothers were confused enough in reporters’ imaginations that Harry’s nickname, “Greasy Thumb,” rubbed onto Jack over time.26 Hard as it may be to fathom today, Jack Guzik and Torrio managed to get a pardon for Harry and Alma from Governor Len Small. As a Republican, Small was dependent upon the Big Bill Thompson machine which, in turn, depended upon the growing Syndicate confederation of Torrio, Eller, and the still-young North Siders to turn out the vote by whatever means necessary.27 Jack Guzik got most of the credit in a similar operation just a couple years later. In 1925 Al Capone opened a storefront office at 2146 S. Michigan Avenue as part of a campaign to pose as a reputable businessman. In early spring, however, Chicago police raided the office and found a set of ledgers that listed on-the-take policemen, the amount each brothel earned, locations of Syndicate breweries, bars and saloons the Syndicate served, and details on international smuggling operations. With Syndicate-unfriendly William Dever as mayor in Thompson’s place, the ledgers could have been a real weapon against the gang. Guzik insinuated he would offer $5,000 to anyone who could recover them. Before the ledgers could make their way to federal authorities, municipal judge Howard Hayes had them impounded and returned. They were never seen again.28 Guzik’s role was so

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prominent in the wake of that incident that at least one newspaper report referred to it as the “Torrio-Cusick-Capone” Syndicate,29 a reference that would recur for years to come. Guzik retained that fixer reputation until he died of natural causes in 1956. We know some of that because in 1941 he repeated the same mistake he’d bailed the Syndicate out on sixteen years before. When he and his wife rented an apartment at an undisclosed “fashionable north shore hotel,” he left several pages of a similar ledger in his oven. Apparently, since he and his wife never cooked, he’d used the oven to hide the documents, and the next tenants passed them along to the Tribune when they realized what they were.30 Among the most salacious details the newspaper published was the fact that someone named “tub” received substantial payoffs. It took a few years to make the connection—one that he always denied—but Chicago Police Captain Daniel “Tubbo” Gilbert, mocked in headlines as “the World’s Richest Cop,” would turn out to be one of the chief investigators in the murders of James Ragen and William Drury.31 In other words, it was likely Guzik’s connections that shielded Patrick and Yaras in their most vulnerable time. And, with Gilbert serving as chief investigator for State’s Attorney Thomas Courtney in 1941, when Courtney was supposed to be going after Guzik, he likely called on those same connections to shield himself as well.32 The 1941 ledgers were only a partial look at the way the Syndicate functioned as it was hardening into the Outfit, but they suggested Guzik was as central as anyone to Chicago organized crime. In a nutshell, they indicated that Guzik took in more money than anyone else. On the basis of that, the Tribune’s reporters declared Guzik the number-one man in the mob, ranking Nitti second, Humphreys third, and Eddie Vogel, the Jewish boss of Cicero’s gambling, fourth.33 Such simple analysis missed the larger picture. Gambling brought in the most money, but it also sent out the most because it needed so much protection from law enforcement. Without stability, without the ability to “advertise” some permanent location or method of contact and then to keep it secure, there’s no way for a gambler to place a bet, and much of the money coming Guzik’s way went on to purchase that stability. Guzik took in the most because he spent the most, spent it in service of the connections the entire organization depended upon. Those ledgers further suggest something that it would take a decade of glimpses and leaks to reveal: the onetime Syndicate—the confederation that had relied on connections across the city—had pulled all those connections within itself. Accardo wasn’t simply the murder chief or the gambling chief, but rather the man responsible for holding everything together. He no more pulled the

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shotgun’s trigger than the president of General Motors tightened the lug nuts on the assembly line. He oversaw everything, but dressed in the topcoat of “the Outfit,” his particular role was indistinguishable from the work of the whole. He was supposed to be as invisible as the killers in a Lenny Patrick–David Yaras hit that went according to plan. As the various facets of the Outfit came into focus, though, as characters like Humphreys, Alex, and Guzik came to notoriety for their role in greasing the gears that protected the gang as a whole, some of their stories started to register. They all started out as cogs in an organization that promised to subsume their individual characteristics, but time and success turned them at least occasionally into front-page characters.

III If you look at a map, Maxwell Street is a lot closer to the Loop than it is to Lawndale. Benny Zuckerman, Davey Miller, Julius Anixter, and most of the other gangsters of Lawndale moved from Maxwell Street as part of a demographic shift, leaping, as it were, the three miles in between. Where they turned left—assuming they were facing north—the young Jack Guzik turned right and found his way just south of the Loop to the Levee where the Capone gang was getting started under Jim Colosimo. There were opportunities everywhere if you had patience and a mind for detail, and Guzik had both. The work was dirty, much of it involved prostitution, but it was lucrative and, barring a little grease on the thumb, it provided enough money to give him security. He would wind up working with plenty of Jewish gangsters over the years—he’d even hire a young prizefighter named David Yaras to be his driver/bodyguard sometime in the 1930s or early 1940s34— but he’d make a name for himself as the most consequential Jew in the history of the Italian-dominated Syndicate. Crime was a family business for Guzik, just as it was for fellow Maxwell Street kids Jules Portugese, Benny Zuckerman, and, a little later, Lenny Patrick. In addition to Harry and Alma, his brothers Sam and Joseph had long careers as Syndicate bookies,35 and his father, Max, was a functionary in the 1st Ward that Hinky Dink Kenna ran.36 In the years before Thompson became mayor, when Carter Harrison made his peace with reformers by cracking down on gambling and vice everywhere but the Levee, there was a kind of proto-Syndicate, a pooling of resources through the jaunty Ike Bloom and onto Kenna.37 Harry Guzik emerged in the forefront of that group—a 1912 report called him one of the “big

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eight of the levee”38—and Guzik was clearly a collaborator. The Levee had striking community rituals—Kenna would oversee an annual 1st Ward ball that brought the city’s elite next to its grubbiest criminals, and Bloom notoriously marched his prostitutes into the heart of the city to insist that vice had its legitimate place39— and Guzik came of age as part of its everyday business of corruption. In a widely told story, since it’s chapter one of the Scarface saga, Colosimo moved to the fore as the Levee declined, slowly pulling his peers into the larger organization he controlled.40 When, as the saying went, “his head got too big for his hat,” and he married a would-be society woman and opera singer, someone— Capone/Camonte in the Ben Hecht version, Frankie Yale according to most contemporary historians41—killed him in his own restaurant. That left Torrio to take over, and he used his position as chief of the city’s largest gang at the dawn of Prohibition to pull together the confederation that would emerge as the Syndicate. His top muscle, so the reputation went, was Capone, while his top “greaser” was Guzik. And, as it happened, the two got along famously. The friendship between Guzik and Capone is the stuff of legend. Capone biographer Laurence Bergreen claimed, “Al’s primary allegiance in the organization switched from Torrio to Guzik,”42 but it seemed more personal than business. While others often complained about Guzik’s hygiene or crude manners, Capone sought out his company.43 Guzik famously introduced him to the pleasures of taking a schvitz at the steam baths and seems even to have taught him basic Yiddish. Capone came notoriously to refer to some of his whorehouses as cheders, Jewish religious schools,44 and he developed such an appreciation for Yiddish culture that he once called for a command performance from Yiddish theater star Molly Picon.45 Their friendship was cemented in 1924 in an incident that established the Capone legend. Bootlegger and slugger Joe Howard reportedly decided one day to push Guzik around. As Capone’s first serious biographer John Kobler put it in an account tinged with anti-Semitism, Guzik, “the globular little man waddled off, wailing to Capone.”46 Capone then stormed into a bar, demanding to know what Howard was thinking. Howard drawled back his now famous last words, “Go back to your girls, you Dago pimp,” and Capone shot him several times in the face, killing him immediately.47 The incident was significant because Capone had only just arrived at the sort of standing where personal killing was beneath him. The story made the front page with Capone referred to as “vice lord of the south side bad lands” and credited with “fame” as the owner of Colosimo’s old Four Deuces nightclub.48 Fortunately for Capone, all the right witnesses got bought off, but it

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was a close call; brazen murder was tough to condone. It would prove to be the last serious personal risk Capone took as a gangster, and he did it on behalf of his Jewish friend. Guzik may have risen to prominence early as a result of that friendship, but he survived well beyond Capone’s fall. While movie versions of Capone’s life generally give the impression the tax evasion charges against him came as a complete shock, the truth is that a number of others—including Guzik, Nitti, and Capone’s brother Ralph—were indicted on similar charges before him.49 Capone’s conviction certainly hampered his career, but it seems likely he’d have remained a significant member of the gang if his syphilis hadn’t robbed him of his mental acuity. Even after his release in 1939, he was sometimes rumored still to be behind the rackets of the city. James Ragen claimed as much in 1946 in the weeks before Patrick and Yaras killed him, but it was Guzik, the most famous Capone loyalist of them all, who spoke for the Syndicate when he declared of Capone, “He is as nutty as a cuckoo.”50 Meanwhile, Guzik was part of the gang as it matured into the Syndicate and then into the Outfit. As part of the inner corruption circle, though—as founder of the Connection Guys—he was generally untouchable.51 The Outfit protected him because the protection he arranged was so central to everyone else. In 1946, when William Drury was first digging into Ragen’s murder, he arrested Guzik and told him he intended to give him a lie detector test. Guzik replied, “Captain, what’s the use of kidding ourselves. If I took a lie test 30 of the biggest men in Chicago would be diving out of high story windows and I’d have to hit myself in the head.”52 And, in perhaps the most telling measure of Guzik’s capacity to see to protection for the gang, Drury and his boss on the police force Thomas Connelly were both reprimanded, charged with conspiring to arrange false testimony, and then fired from the force. As Drury complained in one of his exposés, “There hasn’t been an arrest of a major top flight gangster since [Guzik] was turned loose.”53 Guzik rarely got respect for his influence and accomplishments. In fact, he came in for near constant mockery. When he died of a heart attack in 1956, the Tribune acknowledged his long and central role as a “mastermind” in the rise of Syndicate crime, but it took him to task for a laundry list of petty criticisms. “Small of stature, baggy eyed, and flabby, Guzik did not fit any popular conception of a gang boss. He resembled, instead, a mild mannered retired grocer or clerk.” Additionally, it made fun of him for declining to testify before the 1951 Kefauver Committee on the grounds that it might “criminate” him rather than incriminate.54 His peers Murray Humphreys and Gus Alex never came in for the same level of

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derision, so it was clearly less about his role in the mob than about his appearance, his ethnicity, or his refusing to conform to the model of the gangster that various reporters and law-enforcement officials wanted to see themselves against. Capone had muscle and menace, Accardo quiet mystery, and Humphreys and Alex wily manipulation. Guzik came across as a schlub, which may have contributed to his under-the-radar longevity, and his adversaries could never forgive him for it. In a kind of kicker to his career, he even had a hand in outsmarting investigators when he died. On February 21, 1956, Guzik went to dinner at the St. Hubert’s Grill, a restaurant secretly owned by Murray Humphreys and located on Federal Street in the Loop. There, surrounded by his gangster colleagues, he suffered a massive and immediately fatal heart attack. Humphreys, unfazed over death as a consequence of his line of work, worried that the notoriety might draw scrutiny to his business, so he had some of the others sit Guzik’s body in a car and drive him home where they told his startled wife she should claim that’s where he’d died. The ruse worked, and the story remained buried until former FBI agent William Roemer included it in his 1989 memoir.55 As much as anyone, then, Guzik bridged the space that Zuckerman’s murder revealed. As a contemporary of Anixter and Miller, as someone who left cramped Maxwell Street for the same reasons, he found his way into the Syndicate a generation before the Syndicate found Lenny Patrick. He wasn’t directly a part of the independent Jewish gangster world of Lawndale, but he ultimately ran the economy of protection that Anixter and Zuckerman purchased through Arvey and Elrod. Where Zuckerman was a product of confederation, though, Guzik was an original disciple of Torrio and a leader in the drive toward ever-greater centralization and corporatization. Guzik certainly didn’t pull the trigger that killed Benny Zuckerman, but there’s no doubting he was part of the deliberations. Zuckerman got shot because the Outfit Guzik helped build had no more use for a tough guy who thought he could keep on going it alone.

10 TENTACLES

I Lee Harvey Oswald assassinated John F. Kennedy on November 22, 1963. Two days later, Jack Ruby, who’d grown up around Davey Miller’s restaurant and gym, killed Oswald. Within another week the FBI interviewed Lenny Patrick.1 Other federal agents would meet with Patrick again, and the most significant reports on the assassination—those of the 1964 Warren Commission and the 1978 House Select Committee on Assassinations—would grapple with the potential roles of Patrick, Miller, David Yaras, and assorted other Chicago organized-crime figures. No serious report has ever concluded that the Syndicate or any of its members were behind the events of that November, but that hasn’t stopped a cottage industry of conspiracy theories that implicate many of Chicago’s Jewish gangsters in killing Kennedy. In some circles, then, Lenny Patrick remains famous for the belief that he played a role in a vast conspiracy to murder the president. A Cuban-government–backed documentary made that very claim in 1993, on the eve of Patrick’s second major testimony in the trial against Syndicate boss Sam Carlisi, when it charged that three Chicago mafia gunmen were the actual shooters: Patrick, Yaras, and Richard Cain.2 There’s almost no evidence to support such a theory—conveniently, Yaras and Cain were both dead, and Patrick was in protective custody and unavailable for comment—but it’s not hard to see why the Cubans might have promoted the idea. It put the blame on two of its enemies: Cuban dissidents and the mobsters the Castro regime had banished. Few Americans seemed to take the claim seriously, but it fit a pattern of speculation and imagination around the gangsters that turned them into individuals capable of reshaping American history through their plotting.

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In other words, it used them as characters in escapist stories that others were imagining without full facts, something that could be an occupational hazard for gangsters. As Jack Shadoian proposes, stories about gangsters are an outlet for a reader or a viewer, a way of imagining the experience of being caught in “the particular configurations and contradictions of American society, [of experiencing] a dream in conflict with the society.”3 That is, gangsters make excellent protagonists because we know so little about them and they seem such a potential outlet for aggression. Organized crime shrouds itself in uncertainty. Few gangsters may be conscious of it, but their occupation means they have to try to control the stories circulating around them. They want to be seen as powerful, to appear tied to a syndicate that can punish on their behalf. That way they can get what they want through intimidation rather than actual violence. They also need deniability, though. They need to erase the concrete information that might lead to prosecution or conviction, or else they face serious legal consequences. In that space, in the middle ground between the reputation they need for intimidation and the deniability they need for protection, they create mystery. And mystery, like a vacuum, draws scraps of story into it. Jack Ruby himself made that same point when he testified before the Warren Commission. When Earl Warren asked Ruby about his association with gangsters, he said he did not have any. He acknowledged knowing “persons of notorious background,”4 but he said that was simply a matter of growing up in Maxwell Street and Jewish Lawndale. He admitted he had sometimes edged into dicey employment, such as when he sold tickets to theater shows and boxing matches in the late 1930s and early 1940s, but that was simply a matter of hustling to make a living. “I am as innocent regarding any conspiracy as any of you gentlemen in the room,” he said. “I know when you live in the city of Chicago and you are in the livelihood of selling tickets to sporting events, your lucrative patrons are some of these people, but you don’t mean anything to those people.”5 He was not, he insisted, part of anything larger than the neighborhood where he’d grown up, a neighborhood where Jewish kids learned they had to be tough to survive. He’d killed Oswald, he maintained, simply because he was so offended that someone had attacked the country he loved. As a follow-up to Ruby’s explanation, the Warren Commission spent time investigating Ruby’s ties to what it called “the Dave Miller Gang.” Commission assistant counsel Burt W. Griffin asked Ruby’s younger brother Earl how the experience of growing up around a reputed gangster shaped Ruby’s outlook. Earl Ruby acknowledged that the young Jack Ruby “used to hang around Dave Miller’s gym,”

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but it was, he explained, what teenagers did. When Griffin pushed further, wanting to know if Miller had a “following,” Earl said, “Well, I would say it was—there was a restaurant downstairs and it was a hangout. He owned the restaurant and the gym, and he was a referee so the fighters hung around there and other people came around to see the fighters, so it was a general hangout for people of that type.”6 Griffin, on behalf of the Commission, kept pushing, wanting to know if Miller and his “gang” were responsible for coordinated attacks on Chicago Nazi Bund meetings in the middle and late 1930s—evidence, perhaps, of the sort of organization that might lie behind the capacity for an assassination—but it soon came clear that the Ruby brothers and the investigators were speaking different languages. Both Rubys insisted that Davey Miller and the other gangsters Jack Ruby had known were just figures from around Jewish Lawndale, not players in an international conspiracy. Investigators intent on finding some connection wouldn’t give up, though, and it struck at least some of them that Lenny Patrick and David Yaras had also gotten their start hanging around Miller’s restaurant before getting subsumed into the larger Outfit. A few months into the investigation, an unidentified FBI informant, likely recalling the upheaval around Benny Zuckerman’s murder, proposed that “a close friend of Ruby’s, Abe [sic] Zuckerman,7 was shot because Zuckerman did not cut Leonard Patrick in for part of the proceeds of a gambling operation.”8 In a lead that went equally nowhere, Ruby’s sister Eva Grant reported that Ruby at one point reached such desperation in his failing Dallas business that he called Patrick to see if he could help. As she put it, “In the last year he has had so much aggravation in the club, that he called Lenny Patrick. That was the last resort. He figured he might know somebody—this guy is not a holy man by far.”9 Her point undermined the possibility of conspiracy; Ruby went to Patrick only in desperation, not as an associate. Patrick, for his part, denied any substantial connection to Ruby and certainly to the Kennedy assassination as a whole. FBI agents eventually produced a thirtysix-page dossier and transcript filed as part of the House Select Committee on Assassinations that completed its work in 1978. As Patrick said of Ruby, “I never was what you would call running around with him or anything like that. I knew of him. I knew him when he was a kid. He lived in the next block from me.”10 The subtext of that question, of course, was whether Ruby had connections to organized crime that might run through Patrick or other Chicago Jewish gangsters. As the interviewer delicately put it, “You are regarded as a person who would have knowledge of some of the . . . what we would describe as having knowledge

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of the criminal element during those years, 1946, 1947. You were known to have some associates who could be defined or categorized as being part of Chicago’s ‘organized crime’ scene.”11 The tentativeness of the interviewer’s question showed his growing uncertainty. The fact of growing up in the same neighborhood, of being distant acquaintances far short of friends, seemed to whisper conspiracy in an organized-crime context. Once exposed to the full light of reason, it seemed far-fetched and hard even to articulate.12 Ruby had distant connections to some figures in Chicago organized crime, but they were clearly spent by the time he moved to Dallas.13 So, Lenny Patrick did not kill Kennedy, and he did not kill Oswald. Instead, because he was suspected of having killed so many in his work as a Syndicate operative, he was a character who could be plugged into the stories that others were telling. His supposed involvement in the Kennedy conspiracy, then, is less an additional part of his criminal career and more a tangent. His notoriety as the man who ran Chicago Jewish organized crime for more than a generation made him, through exaggerations of his neighborhood connection to Jack Ruby, an obvious candidate for others’ imagination. Casting Patrick as Kennedy’s assassin makes him into a villain who changed the trajectory of American history. It should have been enough that he’d changed the trajectory of Chicago Jewish organized crime when he led the Syndicate’s takeover of Benny Zuckerman’s operation.

II If Patrick and Yaras’s tentacles to the Kennedy assassination were largely imaginary, they were real enough in several operations that did take them outside the boundaries of Chicago. In the early years of the pair’s “arrival” as prominent Chicago torpedoes, after the Zuckerman and Ragen killings, they invested some of their money in the casino goldmines of Batista’s Cuba. According to FBI reports they joined with Miami-by-way-of-Detroit Mafioso Joe Massei to buy part ownership of the Sans Souci Casino in Havana in 1953.14 It was something of a halcyon period for Patrick who, in his late seventies, shared fond memories of being a big wheel on a tropical island,15 and it’s possible that Patrick and Yaras would have become dramatically wealthy men if not for the Cuban revolution. As it was, they lost their stake in 1960, when Fidel Castro announced he was nationalizing all the property remaining to American investors, many of them—like Meyer Lansky— substantial organized-crime figures.16

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The two also had at least intermittent gambling interests in and around Los Angeles, and the FBI reported Patrick’s comings and goings there for more than a quarter century. As early as 1958, agents determined that Patrick and Yaras were behind a baseball bookmaking operation that used a home-and-emergency oxygen-dispensing company as its front.17 Then, throughout the mid-1960s and early 1970s, the pair was reported to be involved in a gambling and shakedown enterprise that purchased political protection from a close friend of California Governor Pat Brown.18 Additional reports linked them at various times to gambling operations in Detroit19 and Hot Springs, Arkansas.20 Their major focus away from Chicago came in Miami, though, where Yaras bought a home around 195021 and set about exploring a variety of criminal and semilegal operations. Piggybacking off his influence back home, he and his son Ronald helped establish a Teamsters local by 1957,22 one loyal to the rising Jimmy Hoffa faction of the union, with its famous ties to Chicago organized crime. He also eventually owned a vending-machine company23 and a rental-car franchise,24 but those never quite obscured the sense of him as a gangster with his fingers in gambling and shakedown rackets. At least seven years after his move, he was still referred to as a “notorious Chicago racketeer.”25 And in 1967, when Miami FBI agents requested his case be transferred to their branch, the director’s office determined he was still so much a part of Chicago organized crime that he ought to remain part of their caseload.26 Yaras loomed large in his second hometown, bringing with him what the locals saw as a Chicago swagger. A 1959 Miami Daily News story began, “It was just like in the movies,” as it recounted the rumor that Yaras and Massei had gone up to a customer in Sonny’s Pizzeria in Miami Beach, dumped his spaghetti, and started pistol-whipping him. A caller to the paper identified Yaras as the man with the gun, but the reporter could find no evidence to support the story when he arrived an hour later: the place was cleaned up, the victim was nowhere to be found, and the owner explained, “I don’t know nuttin’. I was across the street eating and I saw the police car. I run a nice place and keep my mouth shut.” Police caught up with Yaras on the golf course, where he claimed innocence. Something had happened, the news story explained, but no one could pin down exactly what. The only clear takeaway was that Yaras was a guy to be afraid of.27 In similar fashion, Yaras put himself forward as a big shot in the swaggering mold of Capone and Giancana. He regularly held court at the coffee shop in the Bayshore Country Club. As one FBI informant described it, the telephone behind the bar was understood to be strictly for his personal use. No one else

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could make or receive a call unless he gave permission. He showed he was the boss in other ways as well. When he was displeased with someone, he’d make him wait, lackey-style, in the anteroom. At times he would “brusquely order” subordinates around, making them “sit at another table and wait . . . to be called for such consultation.” When he chose, he played golf. When he didn’t, he seems to have expected the others to laugh at his jokes whether they were funny or not.28 Despite living in different cities, Yaras and Patrick remained partners. Patrick always referred to Yaras as such, and newspaper and surveillance reports regularly linked them. It was hard for outsiders to get a clear sense of their exact relationship. One FBI report gave equal weight to two contradictory claims. It cited one informant who claimed Yaras was “the head man as far as the ‘Jews’ in the ‘Outfit’” were concerned, adding that Yaras “is considered Leonard Patrick’s boss.”29 Then it cited a second source, who claimed, “Dave Yaras and Leonard Patrick were equal partners and that both take orders from . . .” The final name is redacted, but it is clearly a Syndicate figure, most likely then-boss Joey Aiuppa.30 When Yaras died at the beginning of 1974, Patrick flew immediately to Miami where, according to multiple FBI informants, he tried “to salvage his business operations handled jointly with the deceased Yaras.”31 Patrick and Yaras’s involvement in Miami seems strange in light of the standard Mafia myth that every city had its own bosses, but organized-crime observers came to believe that it, like Las Vegas, was an open city where gangsters from a variety of home bases could establish extensions of their original businesses. As one informant explained to the FBI, “Yaras is the Chicago representative of the Miami area for the organized criminal element of Chicago. It is not unique in Miami in that there are several different factions in the Miami area and no one person has control of . . . illicit organized activity.”32 The result was, apparently, that Yaras was free to undertake whatever operations promised to return a profit so long as he could hold onto them. And, through Patrick and with his own connections to the larger Chicago Outfit, he had all the backing he needed. All in all, the “gangster glamour” that drew Patrick and Yaras into the various conspiracy theories around the JFK assassination served them well in their Florida ventures. People knew their story, or thought they did, and that was generally a major prop in their success. They had to deal with harassment from FBI agents, and they had to absorb the occasional news story reminding locals that they were suspects in the killing of James Ragen33 or referring to them as Chicago mobsters when another gangster was found murdered,34 but such stories also insulated them. Yaras could pistol-whip a man or hold court in his country club, and no one

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dared to do anything about it. The two carried the stigma of Chicago—the residue of their work taking over from Benny Zuckerman and rising in the Syndicate— and that meant people in their new city feared them. They got much of what they wanted not only because they had “Chicago” backing them up but because their would-be competitors believed they did. That situation changed with Yaras’s death from a heart attack on January 4, 1974. The FBI agent assigned to Patrick noted “for some reason, his death is being kept as quiet as possible,”35 but the reason was actually pretty clear: without Yaras’s reputation to protect the operations, it was going to be tough for Patrick to keep them going. They’d been a team, but it was Yaras who held down the Miami end of things. Patrick had his own frustrations in Chicago where the grand jury was pressuring him to testify, where he would eventually refuse to talk and be sentenced to four years for contempt. He hardly had influence to spare for the separate Florida front. Both men had connections to Outfit figures who came and went, but it wasn’t clear how much those connections would persist with Yaras gone and neither old-timer on the scene. A little more than three months later, the answer came back. Their respect was gone. On April 18, 1974, Ronald Yaras was murdered in his North Miami Beach townhouse. One unidentified “veteran Miami Beach police officer” told reporters that Yaras “tried hard, and with apparent success, to keep his son Ronald ‘out of the rackets,’”36 but the killing suggested otherwise, as did the fact that Yaras’s other son, Leonard, was one of Patrick’s chief lieutenants back in Chicago. Investigators eventually brought murder charges against two men—former Key West Police Chief Sam Cagnina and Ismael Garcia—claiming they were trying to take over Yaras’s massage-parlor protection racket in Dade County.37 It’s guess work from a long distance, but the obvious conclusion is that the two thought they saw a chance to go after the weakened Yaras enterprises. Months earlier, with David Yaras alive and the specter of the Outfit behind him, that looked like a suicide mission. When Cagnina and Garcia reportedly carried out the murder, it was a matter of killing a shady local businessman who’d just lost his father and whose other main backer was wrestling with legal trouble in Chicago. Up north and without his old partner, Patrick would prove he wasn’t quite finished. He’d emerge from his jail time in 1979 and take back control of his northside crew. He’d make it another good decade before things really blew up for him and he would become, one last time, the stuff of front-page news. Reaching beyond Chicago, though, sending out tentacles that gave Patrick and Yaras influence in Cuba, California, Las Vegas, and Miami, was mostly over. What started

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in Chicago—through Maxwell Street, Jewish Lawndale, and in its final form on Chicago’s North Side—would end in Chicago in a circus partly of Patrick’s own creation.

III During Yaras’s time as a Miami big shot, he extended the gambling operations he and Patrick first took over when they killed Benny Zuckerman. The scale may have been different, but they were playing the same game they’d started back in Lawndale. As part of that, Yaras acquired the Multiple Sports News Service along with “Trigger” Mike Coppola, reputed to be a lieutenant in the New York Genovese crime family.38 On a smaller scale the service provided the same information that James Ragen’s service had—updated scores and horse-racing news—and for which Yaras and Patrick had killed Ragen on behalf of the Syndicate. It meant Yaras, and presumably Patrick, could get profits from gambling without the risk of taking bets directly. They could let others take chances on the front line. Owning the news service meant employing people who knew numbers, among them a transplanted Lawndale kid named Frank “Lefty” Rosenthal.39 Rosenthal was almost a generation younger than Patrick and Yaras, and he’d moved with his family to Albany Park as a teenager,40 but Yaras must have seen something of a kindred spirit. Like his mentor, Rosenthal found his way to the Syndicate at an early age. As a kid, he would skip school to go to baseball games where, in the bleachers at Wrigley Field or Comiskey Park, he got an education in shaping the odds.41 Around 1946, when he was only nineteen, he went to work for Bill Kaplan, an old-school bookie, and Donald “the Wizard of Odds” Angelini, a top Outfit gambling operative, in their downtown bookie joint.42 He developed a reputation as someone who knew what he was doing, but he took a step too far when he was caught trying to bribe a college basketball player and then drew the attention of the McClellan Commission.43 After that, he relocated almost entirely to Florida, working under Yaras and other Syndicate figures who passed through.44 In 1968 Rosenthal moved to Las Vegas where, eventually, he connected with other transplanted Chicagoans. One of those was an almost 300-pound enforcer for Lenny Patrick, “Fat” Herbie Blitzstein,45 yet another Chicago Jew, though, reflecting demographic shifts, a North Sider. Another was Tony “the Ant” Spilotro, an aggressive, small man who emerged as the Syndicate’s enforcer out west, assuming the high-level Outfit post that John Roselli and Marshall Caifano held before him.

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Rosenthal met and married a glamorous showgirl named Geri McGee, established himself as a high-profile Vegas personality with his own local television show, and became extraordinarily wealthy through his share of the Outfit’s “skim” off the nightly cash take from the casinos. Rosenthal’s charmed Vegas life fell to pieces, however, when Spilotro started sleeping with his wife and new leadership in the Outfit determined the situation was out of control. Spilotro and his brother were murdered and buried in an Indiana cornfield in 1986. Rosenthal barely survived a car-bomb attempt on his life as well. If all that sounds familiar, it’s because it’s the story of Casino—both the Nicholas Pileggi best seller and the Martin Scorsese blockbuster film of the same name— and it has become one of the central stories for making sense of the gangster in the last half century. Rosenthal is called Ace Rothstein and played by Robert DeNiro; Spilotro is Nicky Santoro and played by Joe Pesci, but the resemblances are tight. It’s an update of the Scarface story, one that takes into account more of the collaborative character of organized crime. The Al Capone of legend would grab a gun and do the shooting himself. Pileggi and Scorsese saw in Rosenthal’s story a different experience. Here were men who, because they applied their different strengths to their shared crimes, got everything they could ever have wanted. They killed the golden goose, though, when they turned on one another, when they could no longer function as a gang larger than the sum of the individuals in it. After the bombing that nearly killed him, Rosenthal lived a quiet life until dying of natural causes in 2008. One of the few survivors of the gang that Spilotro put together to help out in the casinos—as well as to pursue burglary opportunities that some Syndicate higher-ups frowned on for drawing unnecessary law-enforcement attention46—was Herbie Blitzstein, the onetime Lenny Patrick enforcer, who remained, pun intended, at large in Las Vegas. After serving four years in prison for a counterfeit credit-card scam,47 he reemerged in 1991 as a hustler with apparent Syndicate backing. He owned an auto-repair shop that reportedly served as a front for his lucrative loan-sharking business,48 and Nevada gaming authorities were concerned enough about his influence that they had him listed in the “black book” of figures prohibited from any involvement with state casinos.49 Then, on January 5, 1997, he was found slumped in a chair at his Vegas home. Someone had placed a pistol at the back of his neck and shot him.50 Mob observers regarded it as a move by the Los Angeles and Buffalo crime families to undercut the Chicago Syndicate’s influence in Las Vegas.51 The Las Vegas Sun led off its obituary with the claim that “Herbie Blitzstein was one of the last remnants of a colorful underworld era Las Vegas has outgrown.”52

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As true as that likely was, it was also true that Blitzstein’s murder marked one end of the history of Chicago’s Jewish gangsters. It would take a crooked line to trace a tradition from Jules Portugese and Davey Miller’s Maxwell Street ambitions through Benny Zuckerman’s Lawndale, to Lenny Patrick’s North Side, and finally to Rosenthal and Blitzstein’s Las Vegas, but it’s there if you account for changes in the nature of organized crime, demographic shifts in Chicago’s Jewish community, and transformations in American culture and style. There are almost certainly Jews who remain active in Chicago organized crime, but in the more than two decades since Blitzstein’s murder, none has come close to even his modest notoriety. Whatever tentacles remain to the Chicago Outfit, they don’t seem to reach as far they once did, and they touch only lightly on Jewish Chicago.

11 WHEN SCARFACE MET RICO

I On Valentine’s Day, 1929, Al Capone walked into the office of Miami-Dade County Solicitor Robert Taylor to discuss the recent murder of New York gunman Frankie Yale.1 Fourteen hundred miles away, on the Near North Side of Chicago, police sirens were still wailing as the city became aware of what would go down as the most dramatic gangster massacre in history. Bugs Moran, the Dean O’Banion lieutenant who’d become the leader of the gang that had been crippled in the attack, declared, “Only Capone kills like that,”2 and, so saying, he gave voice to what everyone knew: of course the developing Syndicate was behind the massacre. Capone and his gang had been at war for years with the North Siders, and they were the ones who stood to benefit. They were also among the few in the city with the means to pull off such a shocking crime. The question wasn’t whether Capone was indirectly responsible; everyone knew he was. The question was whether the authorities could prove it. And the answer was no. The St. Valentine’s Day Massacre remains officially unsolved. Walking into a prosecutor’s office was hardly a Scarface thing to do. The movie version of Capone, the Tony Camonte that Maxwell Street kid Paul Muni performed in the 1932 film, would have high-hatted such a “copper,” or maybe just shot him. The same was true of the protagonists of the other most famous gangster films of the era, Public Enemy (1931)—starring a doomed James Cagney and featuring characters named after Chicago Jewish gangsters like “Putty Nose” Anixter and “Nails” Morton—and Little Caesar (1931) with its equally uncompromising protagonist. Like Camonte, Rico Bandello shot his way to the top and then wound up in a gutter, uttering his famous final words, “Mother of Mercy, is

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this the end of Rico?” Such a public image got across the aspect of the gangster as the desperado, but it didn’t address the more substantial challenge of telling the story of the criminal as part of the organized gang. Capone was the man with the scar, the man responsible for the most brutal gangland massacre anyone had ever seen, but his ability to lose himself in a larger gang meant he could avoid personal responsibility. He could even be sitting in a district attorney’s office in Florida with the bodies of his victims still warm on a Chicago garage floor. The situation constituted what we might call a “gangster loophole.” Individual gangsters like Capone and his various successors at the top of the country’s major syndicates could benefit from the crimes of others, but they couldn’t be convicted of them. You can hear the frustration in a government report from the late 1960s when, collectively, the supposed kingpins had escaped prosecution for almost half a century. “The efficient police forces in a particular area may well be aware that a crime leader has ordered a murder, or is an important trafficker in narcotics, or controls an illegal gambling network, or extorts usurious gains from ‘shylocking’ ventures,” the report declared. “Convicting him of his crimes, however, is usually extremely difficult and sometimes is impossible, simply because the top-ranking criminal has taken the utmost care to insulate himself from any apparent physical connection with the crime or with his hireling who commits it.”3 The problem wasn’t a matter of law enforcement—although, courtesy of corruption, it was often largely that—but rather a matter of law. There was simply no direct way to prosecute major gangsters for the crimes everyone knew they directed. The tax-evasion charges that brought down Capone and a number of others reflected one way of addressing the problem, but the approach had its limitations. If a gangster collected money from a criminal conspiracy, he’d have to show its source or go to jail. That made sense legally, but it was indirect. There was something unsatisfying—from the standpoint of justice and efficiency—in convicting gangsters of offenses that were only consequences of their real crimes. The idea was to stop a bunch of murderers who took their money from gambling, extortion, booze, or racketeering, but the actual effort came down to a matter of record-keeping. Legend has it Eliot Ness “got” Capone when his crew of daring “untouchables,” men who couldn’t be bought, shot it out with Syndicate hoods. More of the credit should go to the decidedly unglamorous Elmer Irey, though, the head of the IRS fraud unit, who employed a team of accountants to pore through a decade of Capone’s expenditures.4 And, it’s worth remembering, such efforts managed to put Capone away for only a decade, hardly a fit sentence for the multiple murders he stood behind.

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A more direct way would have made it illegal to benefit from associating with other gangsters, but that approach ran into serious philosophical roadblocks for more than half a century. If Congress made it illegal for gangsters to associate with one another, it would seem to fly in the face of the First Amendment’s guarantee of freedom of assembly. You could make it illegal to do the things that gangsters did—like, say, murder—but making it illegal to be a gangster, to meet with others in a way that could not be proven to be conspiracy, was another matter. Police officials tried varieties of the practice for many years, often arresting well-dressed gangsters for vagrancy or even on the obscure charge of “general principles,” but the practice was patently illegal. Even unskilled lawyers could outflank such a strategy by producing a writ of habeas corpus and getting their clients freed.5 A number of prominent gangsters supposedly even arranged to call their attorneys on the half hour with the understanding that, if they did not check in, they’d likely been arrested and were in need of counsel. Such an approach was really only harassment, though, and even at its best it did little to stymie serious gangster organization. Then came the Organized Crime Control Act of 1970. Senator John McClellan had spent most of the previous fifteen years leading one or another commission on racketeering or organized crime influence. The act was the culmination of his career, and he helped design it, in effect, to close the gangster loophole. For the first time it became illegal to be part of an organization that engaged in a pattern of organized crime, even if an individual within the organization was unaware of the particular crimes that constituted that pattern.6 In addition, someone charged with being part of such a “corrupt organization” could have his assets frozen and be tried alongside the accused direct perpetrators of the crime. The act came under intense criticism from left- and right-wing critics, who saw it as an attack on civil liberties,7 and part of it was struck down as unconstitutional,8 but most of it held. And, as far as organized crime in America went, it changed everything. The most controversial section of the act, the part that expressly spelled out the capacity to target individuals for being part of a criminal organization, came to be known as the Racketeer Influenced and Corrupt Organizations statutes. The acronym, RICO, was a clear reference to the antihero of Little Caesar, the Scarface character who shot his way up in the world only to end up dying in a gutter. While it’s doubtful that McClellan spelled it out so directly, the implication is clear after the fact: Law enforcement could always catch up with the desperado Scarface; every movie cop made that promise and went on to keep it. The failure came in real life when the Scarface character federated with others, when

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he was able to make use of his gang to present himself as innocent while others performed crimes from which he benefited. As such confederation grew more complicated—as the early Prohibition alliances of Davey Miller gave way to the Syndicate of Putty Anixter and Benny Zuckerman and then at last to the Outfit of Lenny Patrick—such gangster bosses had less and less to worry about from ambitious policemen. They could protect themselves with “a lot of buffers” as fictional hit man Willie Cicci put it in his senate testimony in The Godfather, and there was almost nothing the law could do against them. In a nutshell, RICO expanded the existing power to bring conspiracy charges against criminal organizations. Under conspiracy, everyone involved had to be aware of the shared goal of the operation, and the group was defined by its participation in a particular crime. Under RICO, it became possible to convict someone who was part of an organization engaged in a pattern of illegal activity even if some members of the organization were unaware of specific actions or even of the ultimate goal of those actions. As former United States Assistant Attorney Chris Gair put it, “What it allowed you to do was to prosecute people as part of an overarching conspiracy even when they had no knowledge of much of the underlying object of the conspiracy.” Gair would go on to oversee two trials that depended heavily on Patrick’s testimony: a conspiracy to commit extortion against Gus Alex—who was aware of the crimes that Patrick was committing as his subordinate—and a more complicated RICO case against Sam Carlisi and others in which Carlisi did not know all the actions that Patrick and his crew were undertaking on his ultimate behalf. In other words, it took RICO to catch up with Scarface. Chicago’s gangsters recognized the implications of the new law almost immediately. Gus Alex, for one, reportedly became concerned enough that he directed Patrick to stop taking bets on baseball before the 1971 season in order to get a clearer sense of how the law would function.9 In addition, part of RICO permitted prosecutors to grant immunity in exchange for testimony and then to jail someone who refused the offer. Investigators used that provision to jail Patrick’s lieutenant Eugene Lufman in 1973 and then used it against Patrick himself in the 1974 investigation that landed him his four-year prison sentence. On balance, though, it took longer for prosecutors to learn how to handle the law most effectively. The culmination may have come in 1985–1986, when Rudy Giuliani oversaw a prosecution that took out the purported bosses of all five New York Mafia families in what Time magazine called “the most significant assault on the infrastructure of organized crime since the high command of the Chicago Mafia

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was swept away”10 in the 1943 trial that sent Paul Ricca to prison. And, thanks to Jack Guzik’s wrangling Ricca an early release, even that conviction fell short of Giuliani’s team’s success. Before RICO, the best outcome that prosecutors could really hope for was to imprison a key figure or two without deeply reshaping the overall gang. After it, prosecutors managed to arrest entire cohorts of gang leaders, dramatically diminishing the power of traditional organized crime. Retired FBI agent Bill Roemer observed in 1994, for instance, that before 1985, the FBI managed to “turn” only two “made mobsters of organized crime families” into prosecution witnesses. In less than a decade following, the Bureau managed more than a dozen, resulting in the convictions, among others, of New York’s John Gotti and Chicago’s John DiFronzo and Donald Angelini.11 That wasn’t all RICO, but it showed the dramatically extended range that investigators and prosecutors had once they sharpened their use of it.

II When Lenny Patrick got out of jail in 1979, he found a changed world. The Outfit still had clear power in the city, but it had lost the monopoly it held for half a century. When outsiders reflected on the nature of Chicago organized crime, they were as likely to think of the African American El Rukns as they were Al Capone’s successors. Thanks in large measure to the success of the first two Godfather films—the first was released just as Patrick entered prison—the myth of the Mafia was everywhere, inviting both reverence for what seemed a secret tradition and mockery for something that took itself so seriously. And, more broadly, there were dramatic social changes brought on by the end of the Vietnam War, the resignation of Richard Nixon, and a sense that America needed a break from serious affairs. This was the era of disco—within months a local DJ would host a Disco Demolition night that drew a crowd of 50,000 to Comiskey Park—and Patrick was a sixty-five-year-old Jewish man who still wore a hat in public. He remained menacing to a handful of quasi-legal businesses and in a circle of old haunts, but to a growing portion of Chicago he seemed a quaint old man. Meanwhile, the Outfit was retrenching. The mid- to late 1970s saw a wave of killings and arrests, whittling the leadership and the ranks. Most prominently, Sam Giancana was murdered in his own home on June 19, 1975, followed by his onetime ace torpedo Charles Nicoletti less than two years later. Police estimated

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there were twenty mob-related killings between 1975 and 1977, eleven of them with victims under forty years old.12 A Tribune article from May 1, 1977, raised the possibility that the aggressive “young turks” might even try to take out Accardo himself. The same story included an updated leadership chart of the Syndicate, putting Accardo at the top with Joey Aiuppa and Jackie Cerone as the operating bosses; both would be convicted in 1986 from the fallout of the mob’s Las Vegas operations under Lefty Rosenthal and Tony Spilotro. As far as the old-time top guys went, that left only Gus Alex, described as the “roving ambassador trouble shooter” whose work, opined a federal investigator, was clearly cut out for him.13 A Chicago Crime Commission report from 1986 would claim the Syndicate had shrunk from about 300 active members when Patrick began his sentence to roughly half that.14 Within that fading Syndicate, Patrick’s role seemed smaller as well. He couldn’t have known it, but the FBI stopped filing its regular reports on him. They had limited resources, and he simply no longer rated as someone who deserved the near full-time scrutiny they’d given him in the investigations that led to his troubles of 1974. Newspapers and presumably the Chicago Police Department continued to identify him as a captain in the larger structure of the Outfit, but he didn’t carry the same general air of menace. He reclaimed some of his old gambling turf, but he’d seen what RICO could do if he was associated with the operations, so he kept his distance. He also set about rebuilding his crew, collecting a group of men young enough, in some cases, to be his grandsons for the heavy work of threatening and terrorizing the victims of his late-career work. The original second-in-command of that post-prison crew had a familiar name. Lennie Yaras was the Yaras who’d stayed in Chicago, the closest thing to a next-generation Jew the Syndicate had.15 It’s easy to imagine he got his start at the kitchen table, listening to what his father was up to and gradually getting permission to join in. By at least 1970, when he was twenty-eight, he’d become a member of Patrick’s crew,16 presumably returning to Chicago and leaving the Florida operations to his father and brother. He established himself as a collector, making the rounds for street taxes and gambling profits, and he worked his way into at least some racketeering. He managed, for instance, to acquire part-ownership of a laundry business with a local restaurant owner.17 Over time, he emerged as Patrick’s most trusted associate, evidenced above all by the fact that he was the only crew member who ever accompanied Patrick when he met with Gus Alex.18 The Sun-Times’s ace crime reporter Art Petacque called him, simply, “a

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rising star.”19 From that angle it looked as if he was on his way to taking over the “Jewish” wing of organized crime when Patrick finally left the stage. Yaras’s career was short-lived, however, and he was found murdered in his car—with the car set on fire—on January 10, 1985. Witnesses reported four men in ski masks jumping out and shooting him as he waited in front of A-1 Industrial Uniforms at 4200 W. Division. He was forty-four years old. It was clearly a Syndicate hit, the kind his father had participated in many times. Chicago Crime Commission investigator Wayne Johnson speculated that the murder may have been the result of his trying to resist Syndicate chief Joey “the Clown” Lombardo’s efforts to take over Patrick’s gambling interests.20 In any case, the message seemed clear enough: Patrick’s influence was on the wane, and he could not protect everyone who worked for him, not even the closest thing he had to a son of his own. After Yaras’s death, Patrick turned increasingly to Mario Rainone, a wiry tough guy who first made the news when he dynamited a restaurant his aunt’s ex-husband owned.21 Afterwards, he became increasingly notorious for the fearless and aggressive way he’d collect from people he thought owed him. “He’d walk into a restaurant if the guy ‘owed’ him money,” Chris Gair recalled, “and he’d beat him up in front of everybody, a restaurant full of people.” Rainone slid into the vacancy left by Lenny Yaras’s murder. Perhaps as compensation for what seems the crew’s lost gambling operations, and likely as a result of his own proclivity for violence and intimidation, he spearheaded a new foray into juice loans, something Patrick hadn’t been involved with since the late 1960s.22 In addition, he helped oversee street tax, what was left of the gambling, and, most importantly for the prosecutions that would follow, assorted attempts at extortion.23 It’s probably safe to say the crew Patrick assembled under Yaras and Rainone wasn’t the most reliable. Ray Spencer was a longtime associate, but he died of a cocaine overdose around the same time Yaras was killed.24 George Raymond worked as one of his collectors until the early 1980s, when Patrick learned he was cheating him on the cut, and he fired him.25 And James LaValley and Nicholas Gio, despite being intimidating presences themselves, were the sort of terrorists who couldn’t make their munitions work. In 1988, under direction from Rainone, they tried to bomb the Lake Theater in Oak Park as part of an extortion plot. The first time, they tossed a grenade on the theater roof only to see it bounce off the roof and land thirty feet from them; they were fortunate that, instead of exploding, the grenade simply shot off phosphorous sparks. They tried again later that evening, returning with a homemade Molotov cocktail. In the process, LaValley

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set his own arm on fire. When Rainone told them to try a third time, LaValley refused: “He might as well shoot me or bring me to the police,” he said later.26 It wasn’t all Gang-That-Couldn’t-Shoot-Straight misadventures, though. These were still ruthless men capable of real hurt. Days after Patrick was arrested on gambling charges on November 20, 1988—for the first time in the nineteen years since he’d distanced himself from direct gambling oversight after the passage of RICO—seventy-three-year-old bookie Philip Goodman was found beaten to death in a Morton Grove motel. Police suspected Goodman was blamed for the tip that got Patrick arrested. He had nearly $8,000 with him, and whoever killed him left it behind in what appeared to be a “message” to those who thought Patrick had slipped enough that he was ripe for the taking.27 Two years later, eighty-eightyear-old bookie Victor Lazarus was found shot and stuffed into the trunk of his car at 2000 W. Peterson. Police did not link the crime to Patrick’s crew, but an MO similar to Goodman’s, the location just outside his purported turf, and the fact that the victim was a Jewish organized-crime figure make it a possibility.28 Through it all, Patrick stayed in the good graces of the larger Syndicate by checking in regularly with Gus Alex. As he would later explain, he was “with” Alex,29 a standing that gave him license to take part in any number of crimes so long as he got approval in advance and made the proper payoffs afterward. The degree to which he answered to Alex would be a central question in Alex’s trial a few years later, but there’s no question the two kept in regular contact. With the threat of RICO hanging over their heads, though, they had to be careful how they got together. Since both were reputed Syndicate figures for more than half a century, they suggested a conspiracy any time they were in the same room. Patrick would later acknowledge that the two had known each other since the 1940s and been close as far back as the 1950s.30 In a post-RICO world, the two had to make their meetings as inconspicuous and accidental-seeming as possible, and that was a project all its own. They would pretend to bump into each other at a variety of unlikely places: the books section of Marshall Fields, the Hamburger Hamlet restaurant on Rush Street, or one of the visitors’ wings at Northwestern Hospital. Then they might exchange only a word or two, sometimes looking in opposite directions to give the impression they weren’t even talking to one another. In general, as part of a given meeting, they’d make plans for the next one, making sure to leave as little trace of their connection as possible. In the event of an unforeseen eventuality, Patrick would call Max Zimmerman, owner of Zimmerman’s Liquors on the

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Near West Side, to get word to Patrick. Then the two would pretend to be shoppers who just happened to pass in the aisles.31 The substance of their conversations turned on proposals Patrick would make for fresh business opportunities. While government prosecutors would eventually draw a picture of Patrick as a kind of employee of Alex’s and the Syndicate, it might be more accurate to describe Patrick as a licensee. He no longer held the sort of “gambling concession” that Benny Zuckerman had boasted of holding years before in Lawndale, but he did have a kind of right-to-work in the criminal field. He had permission to hustle, to look for ways to bring in illegal income. For the privilege, he had to pay a portion up to Alex. On rare occasions that meant something that smacked at least a little of innovation. For a time in the early 1970s, for instance, Patrick reportedly earned some income through a knack of finding properties the Syndicate could help convert into low-income hotel properties.32 For the most part, though, it meant loan sharking, leaning on businesses that couldn’t approach the police (such as gay bars or adult bookstores), and extortion. If Patrick thought he saw a target that would pay up under threat, he had to get approval first. Part of that was a matter of turf; another Syndicate operative might have a prior claim on the proposed victim. And part of it was simple cover-your-butt; sometimes such people would have unsuspected ties to other powerful Syndicate figures, and going after them could result in serious payback. It’s a shame there aren’t any surveillance photos of the two old men in their meetings. Once upon a time, Alex was a dashing man-about-town, a silver-haired, mysteriously wealthy character who married a fashion model in the early 1950s and then, when she finally divorced him because of his notoriety, took up with a onetime Playboy bunny.33 By the late 1980s, he’d lost weight, grown stooped, and according to several accounts, seemed to be carrying a whole criminal operation by himself as one after another purported boss died or got convicted. In the same way, Patrick had gone from a broad-shouldered, menacing thug to a wispy-haired old man. Each was pushing eighty years old, and neither would have looked to a casual observer as if he were part of a conspiracy any more substantial than figuring out the daily double at Arlington. But the fact remains that the two of them were a crucial link in what remained of the Chicago Outfit. Haphazard and unlikely as their connection may have appeared, it gave coverage to Patrick’s still-violent crew, and it kept one stream of income running into a Syndicate system that continued to corrupt a significant number of elected officials, police, and judges.34 They may have looked like two

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old friends trying to fill their days in the midst of long retirement, but they were actually an extension of the criminal terrorism that started with Prohibition, ran through the murder of Benny Zuckerman, and up through the beatings and murders that Patrick oversaw into the late 1980s. It’s easy to imagine them shuffling around the various places where they got together and even leaning in close to overcome hardened hearing, but they were far from innocent little old men. A lot had changed in the previous decade, but that much was still the same. They were still killers, still the gangsters who’d intimidated much of the city for close to half a century.

III In retrospect it’s hard to tell who blinked first. Supposedly Patrick crew member Nicholas Gio offered to wear a wire to get compromising information against the crew as far back as 1988 in exchange for lenient treatment for a succession of arson and gun charges.35 Instead, it was his partner in bungled explosions, James LaValley, who spoke first and earned ultimate leniency when the charges eventually came for real.36 LaValley’s testimony could take them only so far, though, because he rarely met with Patrick. Instead, he took his orders from Rainone, the second-in-command lieutenant, which meant Patrick himself was largely insulated from such a street-level account of what the crew was doing. The next fish in the food chain was Rainone, and the government took advantage of a clearly rising paranoia within the Patrick crew. With rumors circulating that the FBI was moving in, Rainone was tasked with a more or less routine lock-picking job for another wing of the Syndicate. As he drove to the place he’d been assigned, though, he spotted a car on his tail and thought he recognized notorious Syndicate hitmen Willie “the Beast” Messino and Rudy “the Chin” Fratto.37 Convinced they were trying to kill him, he went into immediate hiding. Whether the Syndicate was actually after him is unclear, but the pressure got to him, and he turned himself over to the FBI. He not only gave a firsthand account of his work as a go-between for Patrick and the rest of the crew, but he also agreed to wear a wire and make recordings of Patrick in the process of conspiring to commit extortion. He subsequently panicked and fled protective custody to go to Italy, but he changed his mind yet again and returned to the United States. Prosecutors had lost patience with him by then, however, and they had his undercover recordings in any case.38 He wound up charged alongside Gus Alex in the first of the two trials where Patrick served as the star witness.

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Rainone’s original willingness to cooperate brought the makings of the entire case together, however, because his evidence gave the government everything it needed to pressure Patrick into testifying against the Syndicate bosses. As the boss of the crew, Patrick functioned as the go-between for the on-the-street thug work of Rainone, LaValley, and Gio and the otherwise “buffered” Alex and Carlisi. Coupled with the testimony LaValley was providing—and perhaps corroborated by elements Gio had at least briefly provided—the U.S. Attorney’s office had enough evidence to put Patrick away for years. More than any other factor, Rainone’s testimony was the leverage to get Patrick to tell his story. As Chris Gair put it, “Mario thought he was in trouble, and that is what actually started the fall of the Outfit.” In 1989, near the end of October, FBI agents Jim Wagner and Jim Martin visited Patrick at his home and made an offer: He wasn’t really the one they were after. He was, they implied, only a medium-sized fish, and they wanted even bigger ones.39 They wanted James Marcello, rumored to be the number two behind Carlisi. They wanted Carlisi, too, if they could get through the buffer of Marcello. They wanted Pat Marcy, the 1st Ward political fixer who’d learned under Jack Guzik himself. And, above all, they wanted Alex, last of the master connection guys from the birth of the Outfit in the early 1950s. If Patrick agreed to wear a recording device when he met with those men, they’d promise him a reduced sentence. That is, if he played ball, he might have a few years left alive as a free man. As part of their offer, they played a tape of Rainone describing some of the extortion plots they’d carried out together. There wasn’t any question. They had Patrick in a vise. It must have felt a little like 1974 all over again, and Patrick responded to the situation in the same way. He initially agreed to cooperate, figuring, it seems, he could find a way to back out later once he’d bought himself time for new options to open up. He tried to talk with Marcello and Marcy, but each seemed aware of a tightening noose, and neither would meet with him. They were, in fact, principal subjects of a separate investigation, one that would result in the spectacular 1993 trial that brought down the 1st Ward wing of the Outfit.40 Alex was another matter, though. Patrick worked under him and met with him regularly. The two already had a scheduled meeting. The old don would never suspect that Patrick, his friend of more than fifty years, would show up wearing a wire. On December 4, 1989, Patrick and Alex met at one of their usual haunts, the sixth floor of Northwestern Hospital. That particular day, the wing was being remodeled and the floor was torn up, so the two old men carried on their conversation as they wandered throughout the hospital. One of the first exchanges may have been the single most important piece of evidence against Alex since

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law-enforcement officials became aware of his prominence as protégé and eventual heir to Guzik and Murray Humphreys decades before. “Here put it this way,” Patrick said to Alex as he handed over a folder of cash. “There’s 7000 there for Zappas, from him, and there’s 4400 for October and November.”41 He was referring to Alex’s cut from street taxes that laundry union head Gus Zappas42 and a couple of the crew’s bookies made as regular payments. The details almost didn’t matter, though, so much as the fact that Alex was recorded accepting payment for a criminal operation. Prosecutors had direct evidence of a business link between Patrick and Alex. They had everything they’d need to bring charges of an organized criminal conspiracy. It was such a tight case, they wouldn’t even need RICO. There was more on the tape, much more, but it was all cherries on the sundae. Patrick would try to undo the damage in the coming months. He would refuse, for instance, ever to wear a wire again when he talked with Alex, and he would violate any number of agreements with the agents overseeing him. Part of his arrangement called for him to receive a $3,600 monthly allowance; for that, he would be obligated to turn over any money he collected through his ongoing operations. Despite his agreement, he routinely held out hundreds and then thousands of dollars, doing what he could to play one side against the other. By April of 1990, he’d had enough, and he decided to stop cooperating altogether. He hired a lawyer, David Mejia, who claimed he could help for a fee of $70,000. Patrick dipped into his own funds, but he also got word to Alex that he was in trouble, and the Syndicate eventually sent him $50,000 in an attempt to buy his silence.43 At the same time, he was also receiving his social-security benefits, income generated from salaries he received for no-show jobs.44 He was dancing on a knife’s edge, though, and there was no way to stay there. Prosecutors announced charges against him, Alex, Rainone, and Gio on December 18, 1991, and by that point he really had no choice remaining. He’d turned over enough evidence that he and Alex would both have a hard time getting off. Both would almost certainly go to jail if he didn’t testify; if he did, there was a chance he’d escape himself. So, on September 16, 1992, seventy-nine-year-old Lenny Patrick walked into court to testify against seventy-six-year-old Gus Alex. Chicago had seen spectacular organized crime trials before, and it had had witnesses with insider information step forward. But no one with a history as long as Patrick’s had ever “sung” before. It was a trial that promised to bring down the last of the original Outfit’s inner circle, and it had a star witness with a story that drew on almost the entire history of the Jewish gangster in Chicago.

12 LENNY’S CIRCUS TURN

I Chris Gair needed a plan. He had to convince jurors to believe Lenny Patrick’s testimony if he was going to convict Gus Alex and Sam Carlisi in the two trials he’d oversee in 1992 and 1993. He and his partner Mark Vogel had the trump card of the recordings in which Alex virtually admitted to conspiracy, and he had the possibilities of RICO to go after Carlisi, but each separate trial still depended on getting Patrick to tell the story he’d promised to tell. After a lifetime of growling at authority, Patrick suddenly found himself the star in two of the most substantial trials ever aimed at the Chicago Outfit. Everything was in place, but Patrick himself was unpredictable, as Gair, lead prosecutor in the trials, explained. “Lenny was fantastically amoral,” Gair said. “This guy was the worst witness I ever had because of his inherent unreliability and his long history of crime and because you never knew what he was going to say. He never cared about what anyone thought, including the judge. He’d just say whatever he thought.” So Gair and Vogel developed a strategy where they acknowledged Patrick’s faults from the outset. In the Alex trial, and then again the following year in the Carlisi trial, Gair acknowledged in front of the jury that Patrick was an extortionist, a liar, and a part of the Syndicate. He even got Patrick to confess to having murdered six people. “An excess of candor is the way to get people to believe,” Gair said. “Most prosecutors think the way to get people to believe their witness is to say ‘That was then. This is now. Yes, they were crooked, but now they’re reformed.’ That is the single most unbelievable thing for regular people. The best predictor for what a human being will do is what they’ve done in the past. You cannot convince a jury to believe a Lenny Patrick has changed his spots.”

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That meant Patrick had to come clean, to own up to everything the defense attorneys would use to attack his credibility. It meant, in effect, that Patrick had to tell his autobiography as he sat on the stand, acknowledging a lifetime of crime stretching back to his earliest days in Lawndale and reviving ghosts no one had considered in decades. Patrick pushed against accepting his role for months. Just as he’d agreed to cooperate in 1974 and then changed his mind, and just as he’d been willing to wear a wire against Alex and then refused to do so a second time, he waffled about testifying up to the very end. But Gair and Vogel kept pushing him, reminding him that, at the bottom line, he had no choice. If he didn’t tell his story—if he didn’t play his part in the two trials—he’d die in jail. It’s a safe bet that few of the people following the Alex trial, whether in the courtroom or in its extensive media coverage, had a clear sense who Benny Zuckerman was. The murder that reshaped Chicago Jewish organized crime was, for all intents and purposes, long forgotten, and it came up as just another detail in the colorful admissions Patrick made during his testimony. The killing of Zuckerman—alongside the murders of Willie Tarsch, James Ragen, “Dago” Vincent Mangano, and a dozen or so others in the middle 1940s—brought about the corporatization of the Syndicate, but by 1992 that chapter was a mostly forgotten step in the process that transformed the Capone gang into the corporation Alex helped oversee. Patrick’s murder of Herman Glick in front of the synagogue when he was only eighteen—a murder that gave him control of a couple of lowlevel neighborhood games—carried as much weight as when he and Davey Yaras took out Willie Tarsch, Zuckerman’s last partner, and ended independent Jewish organized crime in Chicago for good. The goal of the Alex and Carlisi trials was ambitious: to take down what was left of the Outfit. Patrick was only an instrument to that end, but, as such, he was a lens through which Gair and Vogel could give perspective to the long and violent history of the Syndicate that Alex and Carlisi had come to lead. In a way that perhaps no organized crime witness had done in any trial anywhere in the country, Patrick would tell his life story, a story that amounted to a history of the Jewish gangster stretching back to the late 1920s when he ran a craps game in front of Davey Miller’s restaurant. Many of its details seemed impossible, evoking not just a vanished Lawndale but the forgotten conflicts over criminal operations that changing times had erased. There was certainly organized gambling in Chicago in 1992, but it was a far different business from the house-run poker, rummy, and dice games at Zuckerman’s R&K Restaurant or the hidden handbooks taking baseball and horse-racing bets in apartments along Roosevelt Road. Patrick’s

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Chicago mob history—a longtime high-ranking mob official testifying against a man who is reputedly one of the city’s most powerful organized-crime figures.”3 Gus Alex arrived at the courthouse on the first day looking like a caricature of a feeble old man, with a cane in his right hand and a strapping aide supporting him from the left.4 And thanks to Gair’s basic strategy of candor, of putting Patrick on display with all his dirty laundry intact, the circus had its center-ring performer. Chicago had seen high-profile Outfit cases before, but it had never seen anyone like Patrick on the witness stand. He was the star, not just the star witness, and the city hung on his testimony. Here was a relic of the Capone days, a Jewish guy, no less, who talked in an old west-side accent, prepared for the first time to tell where the bodies were buried.5 During the direct examination Gair led him through a litany of the murders he’d been a part of. After his teenage shooting of Herman Glick, Patrick admitted to helping kill Willie Tarsch in 1945. “Davey Yaras shot him with a shotgun and killed him. . . . I was [waiting with the getaway car] half a block away.”6 In 1944 it was Harry Krotish. “I shot him.”7 Then Eddie Murphy in 1950, an old partner shot by Patrick subordinate Hershey Kolven. “I was right there.”8 Next David Zatz in 1952 where Davey Yaras did the shooting. “I was with him.”9 And finally Milton Glickman in 1953. “We shot him.”10 He claimed partial innocence in the case of 31st Ward Republican Committeeman candidate Charles Gross. He just delivered the message, “If you are smart you won’t run or you are going to get killed,”11 so he didn’t count Gross’s murder as one of his own. Gair later acknowledged that was probably only a partial list. Noting the last of those murders took place in 1953, he observed, “It’s hard to believe that he suddenly stopped killing people in the early ’50s.” Longtime Chicago criminal defense attorney Julius Echeles, who represented a number of mob-connected clients in his long career,12 was in the courtroom to observe the performance and took Gair aside with an observation. “Mr. Gair,” Echeles said, “I believe that Mr. Patrick has misplaced a decimal point.”13 Sixty murders would have been overkill, but Patrick wasn’t going to admit to anything he didn’t think others could prove. So there was nothing on Zuckerman’s murder, nor on a range of killings Patrick had supposedly been connected with as a Syndicate torpedo or in support of his own more direct business. There wasn’t even anything on the murder of James Ragen or the follow-up killing of William Drury, the crimes that had briefly made him a national figure, but those were likely too complicated to weave into the larger story he was telling. The six he did confess to were enough to prove the point. He was a violent man who stopped at nothing to keep his gangster operations going.

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recollections seemed like ancient history, even as they formed the tip of the spear pointed at the heart of the Outfit. As a result, when Patrick told the story of his career, it came from a context unrecognizable to most who heard it. To start with, he looked like someone’s zayde, a wispy haired alte kocker old enough to say whatever he felt without filter and without fear of consequences. The very idea of a Jewish gangster seemed more the stuff of comedy than anything to take seriously.1 More pointedly, the fact of the Outfit’s maturing from the confederation model to the corporate one was so subtle as to be almost invisible. Patrick and Alex had been part of that transformation. They’d started in the late years of what was still, in many respects, the Capone gang, a group powerful enough to force all the other gangs into cooperating with it. Soon after World War II that original gang had become the Outfit, had so successfully swallowed the last of the independent gangs that its model of organization seemed the only one possible. Patrick’s earliest stories, the ones about a criminal world of Jews preying mostly on other Jews, reflected a world from before that transformation. They did so, though, not as a history lesson but as part of a contemporary effort to bring down gangsters still functioning in the early 1990s. As Gair put it in his opening statement at the Alex trial, “These aren’t scenes from a gangster movie. They are not an account of Chicago in the 1920s. These are snapshots of the real world, the underworld where threats, violence and terror are a way of life.”2 Gair and Vogel’s challenge was to make Patrick’s story relevant for one purpose: to show that Patrick and Alex had spent a lifetime breaking the law in support of the Outfit. If they could do that, if they could harness the wildcard Lenny Patrick, they had a chance to finish the job that Eliot Ness, Elmer Irey, William Drury, and hundreds of others had attempted from the early days of Prohibition. They could go beyond convicting a handful of serious mobsters and break the apparatus of Chicago organized crime altogether.

II Every trial has its theatrical side. The Carlisi trial would take place around the same time as the notorious O. J. Simpson trial with defense attorney Johnnie Cochran’s famous chant of “if it doesn’t fit, you must acquit.” The Alex trial was earlier, but it was already in the vein of trial-as-performance. The Tribune opened its coverage with the claim that “nothing like it has happened before in the storied annals of

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Gair led Patrick through a more recent list of the assorted gambling and extortion he’d overseen as part of Gus Alex and Sam Carlisi’s Outfit. Patrick confessed to taking in $850,000 in 1969 when the New York Mets’ World Series win and the New York Jets’ Super Bowl victory provided two betting upsets.14 He admitted to loan sharking. He said he’d received $200,000 from Carlisi and his associate James Marcello to loan out at outrageous rates.15 “Sometimes you charge the man as far as a thousand dollars,” Patrick testified. “You charge him like $50 for the week.”16 That meant, in theory, a $1,000 loan could command a repayment of more than $2,500 over the course of a year, provided the victim could be made to keep up with his payments but never reach a zero balance, and even more if the victim fell behind on the interest or “vigorish.” He also admitted to extortion. As just one example, he admitted getting gambler Yussie Meyers to give him $150,000. He said he flashed a gun and then “I threatened him I would kill him if he didn’t give me the money.”17 He even talked of extorting two of his own nephews. “I shook his son-in-law down,” he said of his brother Mike, “and then I got my money fast.”18 He did more or less the same to his wife’s nephew a few years later. And then, he admitted, there were the times he perjured himself or lied when he was giving testimony. During the Alex trial, Gair asked him on the stand, “Despite the fact that you were under oath, despite the fact that you had immunity, did you tell the truth or lie before that federal grand jury back in 1974, or did you do some of both?” “I done some of both,” Patrick answered.19 That meant he’d lied when he said he had no gambling income, when he denied getting street taxes, when he claimed he’d never run juice loan operations, and when he said he knew nothing about the murder of Boodie Cowan even though he knew his brother Mike was responsible for it.20 He also said he understood it was a simple matter of testifying or going to jail for the rest of his life. He’d refused to testify in 1974, and that earned him a fouryear sentence for contempt. This time, during the Alex trial, it was even more serious. Over the objections of the defense council, who were as unnerved as Gair about the sort of things an unrestrained Patrick might say, he volunteered that jurors should believe him this time. “[If I] get caught lying, I am gone,” he said. “I don’t want to die here. That is all. Maybe I ain’t got enough guts to die here.” Again, such a confession came in the service of the case Gair and Vogel were making against Alex and, later, Carlisi—that Patrick was able to do the work he did because he took part in the collective violence and lawbreaking of the Outfit. And since those arguments took place in the context of the RICO law, Patrick’s testimony provided the crucial link between the on-the-street violence

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of the documented extortion and murder and the otherwise insulated heads of the Outfit. Thanks to the undercover recordings Patrick got, the Alex trial was brought forward under easier-to-argue conspiracy to commit extortion charges, but the Carlisi trial was one of the first organized-crime RICO cases in Chicago. In both instances, the point was to hammer home the notion that none of Patrick’s crimes could have taken place without the complicity of Alex and, in later years, the blessing of Carlisi. Gair had Patrick lay himself bare so there’d be no reason for jurors to doubt him. It was a simple plan, but nothing that depended on Patrick’s following a script could ever be simple. Still, by talking so candidly about the crimes he’d committed throughout his long life, Patrick bought credibility for himself and for the larger case against Alex, and later against Carlisi. He gave jurors every reason to hate him, every reason to see him for the untrustworthy criminal he was. But that candor was a down payment on the eventual overall claim. If Patrick had stopped lying about things as serious as shaking down his own family, committing perjury, and performing multiple murders, then, the theory went, he had certainly stopped lying about his role in the larger Outfit. You could trust him, or so Gair and his associates hoped the jury would decide, because he’d just shared the things he’d spent a lifetime hiding from the world.

III With Patrick, though, it wasn’t just what he said. Above all, it was how he said it. John Gotti was prosecuted in a series of trials in the late 1980s and early 1990s,21 and if he represented one kind of gangster—the preening Scarface who’d killed his way to the top—Patrick represented an older, almost forgotten variety. Gotti sneered. Patrick shrugged and kvetched. Patrick was a Guys and Dolls figure come to life, an old-timer who’d had his ups and downs on the way to an improbable career. He wasn’t trying to be funny or to perform as a character. He simply was a character, a seventy-eight-year-old man who, originally a tough Jew in an everyday world of tough Jews, emerged in the trial as perhaps the last of his kind. He told, for instance, of the time his car got stuck and a young pizza-delivery driver came to his assistance. “I was on Cicero near Peterson one day and I got stuck in the pavement there by the curb,” he said. “This truck went by and this fellow stopped and he had ‘Father and Son Pizza’ on here. He helped me. He pulled me out of there. And I wanted to give him a few dollars, but he wouldn’t take it.”

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But the act of kindness stirred Patrick’s imagination. He knew the pizza chain. As far as he could tell it was international, and he figured that meant some potential for a serious shakedown. So, after clearing it with Alex—a point central to the charges of conspiracy to commit extortion that Alex faced—he set his lieutenant, Mario Rainone, to the job. “I told him to ask for 300,000. I told him there was a big business; they were all over the world. And I told him to go ahead and see what they can do with it, that’s all.” The crew wound up getting nothing that time, but the thought process was so sociopathic as to be funny. If not for the driver’s stopping to help him, it would never have occurred to him to go after the business. On another occasion in direct examination, Gair asked about $165,000 Patrick had loaned to an old Lawndale acquaintance named Al Mincer. The point of the question was to establish Patrick’s role in juice loan operations, an operation that would link him to both Alex and Carlisi. But the mention of the name clearly set Patrick off. Mincer, it seemed, had presumed on their old friendship—“I was in the orphan home with him” Patrick claimed—to get the capital, and then he’d left the city rather than put it to work loaning it out. “Personally, he took me for 165,000. I got taken, too,” he ranted, angry at the sense of himself as victim. He wasn’t finished, though, and even though he was on the witness stand in one of the most high-profile organized-crime cases in Chicago history, he couldn’t let the point go. “I’m supposed to be the con man. They conned me everything I had. You might as well know it. I don’t want no tag day. I figure I’ll get out of here someday. When I’m a hundred years old I’ll get a job somewhere. I don’t know where. Anyone want to give me a job?” he asked the courtroom audience. “I mean this sincerely. It’s the truth. I’m not kidding. It’s no joke.” After Judge James Alesia admonished him to just answer the question, he kept going. “I’m sorry, I’m sorry. I think I’d sell a few cars, though. I’m sorry, okay, Judge.”22 The real fireworks came during the cross-examination, though. Patrick had been unpredictable enough when prompted by Gair, who’d prepped him for the stand and described in advance the questions he intended to ask. It was even more of a crap shoot when he found himself facing questions from one of Alex’s attorneys, Sam Adam, whose defense strategy focused on making Patrick appear unreliable. In almost sing-song fashion, Adam tried to establish the idea that everything Patrick did was because it was “best for Lenny Patrick,” no matter the cost to anyone around him. The whole point of his cross-examination was to unsettle Patrick, a guy who didn’t seem all that settled even when he was following the script he’d agreed to with Gair and Vogel.

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Early on, Adam asked about the Herman Glick murder, Patrick’s first. Patrick liked to think of the killing as self-defense, but that was hard to assert with a straight face since he’d lain in ambush and shot the man from behind. Adam pushed him on the point, drawing out the fact that, even if Patrick and Glick had fought, the fight took place days before the murder. Patrick eventually snapped back. “I done it to protect myself. I don’t deny doing it. I just don’t shoot people to get a kick out of it. If it wasn’t me—if it wasn’t him, it would have been me. That is what would have happened. That is why I done it.” When Adam pushed back that Glick was unarmed at the time, Patrick responded. “He didn’t have a gun with him. He had plenty of guns, don’t worry about it.”23 Adam then turned to the murder of Willie Tarsch, last survivor of the Zuckerman gang, and he drew out the notion that killing Tarsch allowed him to take over gambling on the West Side, taunting him with the refrain that doing so was “best for Lenny Patrick.” Patrick fired back again. “I do what everyone else was doing,” he said. “I am talking about everyone else too. So you are putting me in the litter there. I will put it right back to you. I am telling the truth. Everyone else done the same thing. Your client done the same thing too,” he said. When the judge again pushed him to answer the question, he had to get the last word in. “I am sorry, I will say to the court. But I just want to let him know. There is no saints in this room.”24 At times it wasn’t clear whether Patrick meant everything he said or whether he was playing a game. Adam pressed him on the idea that, for years, he’d paid bribes to Arthur Elrod as protection for the Roosevelt Road gambling he’d taken from Zuckerman. Adam asked a series of questions calling for the name of the individual Patrick supposedly paid off, but he dodged the point until Adam pinned him down. “I was close with Alderman Elrod,” Patrick finally acknowledged. Adam pushed on. “Was that one of the ones you were bribing?” he asked. “I did. So what? I did. If you want me to bring the guy’s name out. The guy is dead. Do you want me to bring him down, bring him up from the dead? I did,” he said. “They are the facts. I try to save the man’s name, but you want to bury him.”25 Later in the questioning, Adam tried to establish the idea that Patrick controlled his own crew, leaving open the possibility that Alex was nothing more than a convenient dupe for this lifelong self-serving gangster to blame for his own crimes. In an effort to underscore the brutality of the operation, Adam asked whether it was true that Patrick had sent his top two enforcers, Rainone and James LaValley, to threaten “legitimate everyday street people” with the warning, “We are going to kill you. We are going to kill your children. You will all be in Mt. Carmel.” Patrick

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acknowledged the gist of the question, but had a minor correction. “Mt. Carmel or Weinstein’s,” he said. “Don’t leave the Jews out.”26 And, perhaps most memorably, Adam asked him about the murder of Harry Krotish. In doing so, though, Adam referred to Krotish as “Harry the Horse,” a nickname borrowed by newspaper writers of the time from Guys and Dolls rather than from actual Chicago history. The maneuver confused Patrick at first, who finally observed. “He didn’t have no horse.” Adam tried to draw him out as making fun of the trial process, proposing, “Well, this may be very humorous to you.” Patrick ran with the suggestion. “It is humorous because he didn’t have no horse. You better read the paper again. The name is right. But he didn’t have no horse. If he did, I would have jumped on with him.” Adam, of course, was not amused, and Patrick’s antics brought about an exchange between Adam and Gair, unsettling the cross-examination for a time. When things calmed down, Adam tried his question again. “Do you remember being questioned about Mr. Krotish?” Adam asked. “I remember being questioned about him. I don’t remember anything about a horse, about his name was a Horse. I am not trying to be funny. I am telling the truth.” Patrick said. Adam regrouped and asked, “Tell us how that murder took place.” Patrick’s answer may have taken a long time to draw out, but when it came it was a reminder of the seriousness below the banter. Patrick said, “How did it happen? He got shot like anyone else. He got shot and he was dead.” Adam followed up, “Who shot him?” Patrick replied, “I shot him,” showing far less emotion about killing a man than over the question of whether the man went by the nickname of “Horse.”27

IV And yet it worked. Gair and Vogel’s strategy to have Patrick acknowledge all his crimes without remorse, to embrace Patrick’s candor as the best way to establish his credibility, led to convictions in both trials. Gus Alex was ordered to pay a fine of $823,000 and sentenced to sixteen years in prison, where he died in 1998.28 Sam Carlisi was convicted in 1993 along with James Marcello and six other mob figures. He was order to pay $125,00029 and was sentenced to twelve years and seven months;30 he too died in prison. He’d appealed his conviction and, with the appeal pending when he died, the government eventually vacated the charges.31 Either way, the top targets of the two separate trials were in prison. Prosecutors had taken down the last of the key “connection guys” as well as the supposed boss of the whole Outfit.

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There was even more, though. Two Outfit trials from around the same period added to the impact. The 1992 conviction of west-suburban boss Ernest “Rocco” Infelise and the 1993 prosecutions of 1st Ward powers Pat Marcy and Fred Roti, meant four almost simultaneous hits. Many observers of the time predicted the likeliest figure to emerge as the boss of a reconstituted Outfit was Carlisi’s righthand man, Marcello, who was young enough to expect he could serve his sentence and be released. Investigators obtained crucial information by bugging his prison area, however, and he was eventually convicted again in the last of the major Outfit trials of the era, the 2007 Family Secrets trial. As a consequence, the mob was so broken that, as far as Federal investigators are concerned, it is no longer a substantial threat to the Chicago public. “I’m sure it still exists,” Gair said in an interview after he’d left the US Attorney’s office. “There are still some cats and dogs, but the US Attorney’s office dissolved its organized crime unit. I mean, Chicago La Cosa Nostra is not a factor.”32 Put differently, those five trials collectively toppled the Syndicate that had run Chicago since the early years of Prohibition. No one person was responsible for the whole, but Patrick was the central witness in two of them, and the crucial evidence in a third came as a result of an imprisonment his earlier testimony produced. As late as the early 1990s it would have been unthinkable for the Outfit to be finished. By the time the Family Secrets trial ended fifteen years later, the unthinkable was real. Patrick’s testimony, his “flipping” to the side of the prosecution, may well have been the single largest factor in tearing apart the gang that made Scarface possible. There were hiccups along the way. Between the convictions of Alex and Carlisi, both overseen by Gair and Vogel, Patrick served as a witness in another 1993 trial against Carlisi in San Diego. In that case, however, Patrick seemed to realize the implications of his having confessed to six murders without spelling out a formal plea agreement in advance. He was, observers noted, liable for a sentence as long as 120 years.33 Likely as a result, he told his story differently in San Diego, insisting his victims “went for a pistol” before he shot. That got him a perjury charge and, after he negotiated again with Gair, he had his original six-year sentence for extortion extended to a seventh year. It was a close call for him, though, and he might easily have crashed the entire operation. As it was, Patrick concluded the two major trials with the prospect of state murder charges hanging over him. He began his time in federal prison, in a unit designed for witness protection, unsure what his future might be. Over the next few years, though, the state’s attorney’s office slowly let the cases slide. They were

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so long ago, went some of the reasoning, that there were no credible witnesses, and the remaining materials were incomplete. In addition, Patrick himself was aging, and it wasn’t clear he’d be competent to stand trial.34 As it turned out, he never faced charges for the six killings he admitted to or for the who-knows-howmany more he was suspected of. Sometime in the middle of 1998, not long after Alex and Carlisi died in custody, Lenny Patrick got out of jail himself. As a former cooperating witness, he had the opportunity to ask for placement in the witness protection program. That might have taken him to a small town in Minnesota, Oregon, or Arizona, but as former prosecutor Gair put it, “He didn’t know anyone in Arizona.” Instead, and to the surprise of many who’d imagined after he agreed to testify that he’d one day go down in a hail of gunfire, he asked to move back to Rogers Park, back to the remnant of the Jewish community he’d migrated with from greater Lawndale. If he committed any further crimes in his final years, he pulled them off without a trace. He lived there, unharmed, for another seven or eight years. No one attempted to hurt him because, as Gair put it, “Everybody was in prison.” And that was the end of that line of the Jewish gangster in Chicago. Lenny Patrick had reshaped that history with his part in the murder of Benny Zuckerman. He’d been the point person in subsuming that largely independent operation into the machinery of the larger Syndicate, and he’d been at the head of the Jewish wing as the Syndicate slowly morphed into a full-blown corporation of crime. Then, as much as any one person, he was at the heart of bringing down the Outfit, of leveling the organization that had been behind his takeover of the old Lawndale gangster world. The first half of the story of the Jewish gangster came to a culmination when Zuckerman knit together the independent gangs of Putty Anixter, Davey Miller, Morris Eller, and dozens of other forgotten Maxwell Street and Lawndale toughs. It ended on Zuckerman’s bad day, the day Lenny Patrick or an ally shot him as he lingered before his apartment door after a long afternoon of pressures from organized-crime rivals. The second half of that story ended without such Scarface fireworks. Instead, it wound down with a shuffling Lenny Patrick, an old man slowly fading in a neighborhood he’d terrorized for half a century. By the end, Patrick had become so low-key, so removed from his career in crime and his brief circus turn as a star witness, that even news of his death took months to become public. It was, against all odds, natural causes. Somewhere, it’s easy to imagine, the long-dead Benny Zuckerman must have thought that was a pretty good day, even if it was a long time coming.

Afterword A QUESTION ANSWERED

Not long ago I got an inquiry from a man named Jerry Levine. He’d just read John Binder’s Al Capone’s Beer Wars, and he wondered whether it was possible that his father, Ira “Sonny” Levine, was part of the group of Jewish gangsters that John referred to as the “20th Ward Gang.”1 Sonny Levine sounded impossibly colorful; he’d run away from his home in Michigan’s Upper Peninsula, joined a circus, and found himself as a teenager in Chicago at the dawn of Prohibition. After a career that involved running booze to Canada and various safecracking work, he retired from crime and worked at a hardware store where, after being called upon for legitimate work opening safes for people who’d lost keys or combinations, he’d show off at home by cracking random bike locks for the fun of it. He talked occasionally about his early gang days with a man named “Nails,” but otherwise he shared impressions rather than details. He died without telling Jerry anything like a full story. Jerry wanted to know if I could fill in the context, and I tried. The 20th Ward Gang was one way of referring to the various tough guys, gamblers, and gangsters who’d worked under Morris Eller when, in the Capone-ruled middle days of Prohibition, Eller controlled most of the police protection around Maxwell Street and into the burgeoning Jewish Lawndale. My own family, the Miller Brothers, were an early part of that loose network and, of course, Hirschie Miller was a onetime partner of Samuel “Nails” Morton, likely the figure Sonny Levine recalled. Others from that group went in different directions, some like Morton allying with the North Siders, others drifting under the umbrella of Jack Guzik and the Syndicate, and still others filling in the ranks of Benny Zuckerman’s operation before it too got swallowed by the Syndicate. They often fought among themselves, with some like Jules Portugese flaming out when their ambition overshot their opportunities. Most, though, like Jerry’s father, lived on the edge of the law, staying just clear enough of real trouble not to leave a permanent mark through the newspaper or arrest records. And their gangster stories are visible

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only as part of the larger one that runs from the stirrings of Eller’s predecessor Manny Abrahams, through the greater Lawndale experience that culminated in Zuckerman, and onto the Syndicate career of Lenny Patrick. I wish I could tell Jerry Levine even more, but, collectively, we have done a good job of forgetting. Two generations after every kid within a mile of Douglas Park would have known to call Davey Miller’s boys in a pinch, the very idea of a Jewish gangster can seem like the set-up for a joke. Thirty years after my mother asked me whether Dean O’Banion had killed her father, I have an answer, but it’s too late. She passed away only recently, but dementia left her remembering nothing in her final years. Still, I get questions like hers, or like Jerry’s, fairly often. Someone’s father-in-law had a phone line installed in a closet and went there to take private calls; someone’s great-uncle was “connected” to the Italians in the 1950s, and someone’s grandfather had a cousin named Max Eisen who may have been involved in the rackets. Until now, though, I have had no way to suggest how the separate strands of the Chicago Jewish gangster experience come together. I hope, then, that this book answers questions from a lot of curious descendants, but I hope even more ambitiously that it helps to fill in the blank space between Jewish history and the history of the gangster. It is, as far as I can tell, the first full account of the Chicago Jewish gangster, and maybe it will help give perspective to the generations that immigrated to, grew up within, and eventually moved throughout the city. I was fortunate to spend a number of days at the Maxwell Street market, that remnant of the place where so many of Chicago’s Eastern European Jews made their first homes. Manny Abrahams once ruled it, and Morris Eller used it to assemble the financial and thuggish power behind his political rise. The market I knew was just a slice of the bustling bazaar that was an extension of that community. Even so, it had a trace left of the ragged, corrupt charm of the original. I took a class to visit it one summer day in the early 1990s—we were reading immigrant fiction—and we saw at least three shoplifters racing from vendors or police as they held onto whatever they’d managed to grab. The market is now gone almost entirely, reinvented as a cleaner Sunday tourist destination, but what’s there is in part a memorial to the original. Thousands of Chicago Jews started their legitimate careers there, but so too did dozens or even hundreds of shtarkers, tough guys who’d go on to plague the city for a generation. I knew Jewish Lawndale less well, mostly from driving through it, but I did make it a point to visit sometime around 1997. I parked at the intersection of Roosevelt and Kedzie, got out, and stood in front of 3216 W. Roosevelt, where

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Davey Miller and Benny Zuckerman once held court, two doors from where Jacob Arvey and Arthur Elrod ran the 24th Ward, and a handful of blocks from where Lenny Patrick and Davey Yaras killed Willie Tarsch. The old building was gone, torn down within the previous year from the looks of it, but I’d come in time to see the footprint it left. I stood a few minutes trying to imagine what it must have been like in the days of the Miller brothers and Zukie the Bookie, when it was bustling with young men wanting to have a go at it in the ring and older men hoping the dice or the cards would go their way, when it was a place so casually corrupt that the “boys” would park a baby carriage in front of any place where the gambling was happening.2 I lifted the chain hanging between two poles and slipped in. I gave a quick look over my shoulder and, when I was convinced no one was paying attention, grabbed a pair of bricks—one last crime for the Miller family in Lawndale. I still have the bricks. Their only distinction is a residue of paint on one side, a ghost-white color suggesting things were once much brighter. Or maybe it’s just my imagination. Maybe the bricks were always simply pale. Such uncertainty is a good check on me as I try to reconstruct a story no one has ever told start to finish, the story of a tradition that extended before and beyond the awareness of most of the gangsters who were a part of it. Thanks to newspapers, the Chicago Crime Commission, the records of the police and FBI, and people who shared their memories later in life, hundreds of facts and anecdotes survive from the Lawndale that Lenny Patrick took from Benny Zuckerman, but each of those is like a brick. It suggests the whole, it implies a larger structure, but it can also mislead. I have tried to tell the story of what it was like to live in a place that’s been dismantled, of a gone-place where young Jewish men who seem impossibly different from me fought as gangsters for a “concession” not just vanished but almost inconceivable. I am certain I have made mistakes, though. The scraps of fact and story I have pulled together can only hint at the fuller edifice that’s vanished in Jewish Lawndale. And then, like so much of the Jewish community as it migrated across Chicago, I lived for several years on the North Side, and there I found further echoes of the gangster past. I’d stop at the Chinese restaurant that stood on the spot where my father’s mother and stepfather once ran Joe Stein’s Rumanian Steakhouse, where Joe would—according to family lore—plug his ears and leave the room when Matt Capone and other Syndicate figures started talking business. My aunt once tried to set me up with a woman who turned out to be connected to the Anixter family, and though we never had a second date, I laughed to myself at the idea of

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patching up the long-ago feud between my family and hers. I thanked my aunt for looking after me by buying her flowers at the florist that opened just next to the remains of the Marigold Gardens where, during the later years of Prohibition, Davey Miller’s protégés and various gangster-backed fighters got their chances to fight as professionals. I went to the Green Mill, a bar that still operates as a slice of the Green Mill Gardens where, as a poem on the wall commemorates it, Capone lieutenant “Machine Gun” Jack McGurn tried to kill Joe E. Lewis. And my wife and I bought a condominium that turned out to be half a block from the mansion that Joe Aiello built with the profits he took as an ally of the North Siders before he too turned into a victim of the Syndicate. Throughout those years I began to feel as if I were a witness to a story that unfolded so slowly—and then vanished so completely—that I was one of the only ones to recognize its narrative. Various crooked politicians and ambitious gangsters fought with one another for more than eight decades from the Near West Side to the “far west” of Lawndale and then up north to Rogers Park, Hyde Park, the lakefront, and the suburbs. Some of them were still alive, keeping their stories even from their own families, but most were gone. Lenny Patrick’s testimony brought back some of it, but only briefly and without the context of the deeper history it stood on top of. Then it was quiet, and while I tried to dig up chapters of the story, there were fewer and fewer people left to ask about it. I didn’t know at the time—the government doesn’t advertise it when it releases someone from the witness protection program—but one who did remember was Patrick, a nonagenarian shuffling down familiar Rogers Park streets, slowly forgetting stories that only he had known in the first place. I have told as many of those stories as I can in this book. I have tried to answer the question my mother asked when she urged me to look into her father’s story, when she gave me that first bizarre piece of the puzzle of Chicago’s Jewish gangsters. It hasn’t proved a neat story. There’s no Scarface at the heart of it, and the nature of the organized crime it deals with changed in step with the ever-changing Chicago corruption around it. Still, it is a story. It started when a group of immigrant young men tried to make new lives for themselves on a Maxwell Street that wasn’t quite the street of gold they’d been promised. It ended when a vicious old man took his final stroll along a Rogers Park side street. And it took a dramatic turn that January evening in 1944 when Lenny Patrick and the Syndicate put three bullets into Benny Zuckerman and forever altered what it meant to be a Jewish gangster in Chicago.

CAST OF CHARACTERS

Italics indicate that an individual is not Jewish Abrahams, Manny—Maxwell Street–area politician and gang boss. He rose to his peak influence during the Carter Harrison, Jr., years, and famously died during a City Council debate. Accardo, Tony—After Al Capone, perhaps the most significant gangster in Chicago history. He was regarded as one of the Outfit heads from the middle 1940s until his death in 1992. Aiello, Joe—Successful bootlegger who allied with Roger Touhy, Jack Zuta, and the remnants of the North Side Gang in the wake of the St. Valentine’s Day Massacre. He was machine-gunned to death in 1930. Alex, Gus—Greek American “fixer” and longtime leader of the Outfit. Convicted as part of conspiracy charges made possible through Lenny Patrick’s 1992 testimony. Anixter, Julius “Lovin’ Putty”—One of the pioneering figures of Jewish Lawndale and a largely behind-the-scenes power broker from the 1910s until his death in 1943. He provided the organizational and political backing for Benny Zuckerman’s rise to preeminence. Annenberg, Moses—Beginning as a circulation manager for various Chicago newspapers, he rose to wealth and prominence by acquiring the wire service on which gambling operators depended. He eventually sold his interest in the wire to James Ragen and went on to become a major newspaper and magazine publisher before being convicted of tax evasion in 1939. Arvey, Jacob—The most influential and long-lasting Jewish politician of the greater Lawndale era. While never convicted of law-breaking himself, and while famously promoting progressive and egalitarian causes, he had clear links to organized crime. Blitzstein, “Fat” Herbie—Onetime Lenny Patrick enforcer who relocated to Las Vegas as part of Tony Spilotro’s gang. Killed in Las Vegas in 1997. Block, Harry—Brother-in-law of Davey Miller and owner of a Maxwell Street restaurant and gambling center in the 1910s and early 1920s.

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Block, William—Partner with Lenny Patrick and David Yaras in the botched 1946 shooting of James Ragen. Bloom, Ike—Colorful chief lieutenant in Hinky-Dink Kenna’s pre-Prohibition vice and political corruption operations. Capone, Al—Internationally recognized as the scar-faced head of the gang that grew from first-among-equals in the confederation that Johnny Torrio assembled to the monopoly it would hold as the Syndicate over Chicago organized crime for two generations. Carlisi, Sam—Regarded as operating boss of the Outfit from around 1989. He was the primary defendant in the 1993 RICO-based trial that featured Lenny Patrick as the key witness. Cermak, Anton—Bohemian saloon keeper from Czech Lawndale who assembled the Democratic machine that ultimately supplanted Big Bill Thompson’s Republicans. Some speculate that his 1933 assassination was in retaliation for his attempt to kill Frank Nitti. Colosimo, “Big” Jim—1st Ward brothel owner who came to dominate gambling and organized crime in the late 1910s. His murder allowed Johnny Torrio and later Al Capone to take over the largest gang in the city. Connelly, Capt. Thomas—Chicago Police captain and superior of William Drury. He supported Drury in his investigations of Lenny Patrick and David Yaras after the 1946 murder of James Ragen and was fired from the force as a result. Dann, Louis—Partner and lieutenant of Benny Zuckerman. He fled Chicago after Zuckerman’s murder but returned after Jacob Arvey negotiated his safety with Syndicate leaders. Dorfman, Allen—Outfit financier who helped funnel Teamster pension funds into Las Vegas casinos. A victim of a 1970s Lenny Patrick extortion scheme, his 1983 murder is depicted in the film Casino. Drury, Lt. William—Chicago Police investigator who pursued Lenny Patrick and David Yaras over the murder of James Ragen at the expense of his own career. His murder in 1950 shocked the nation but also effectively ended significant law-enforcement attention on Patrick for at least the next decade. Eisen, Max—One of the most prominent Jewish figures in the North Side Gang. He was credited with chairing an organized crime-peace conference at the Hotel Sherman in 1926 and survived the Prohibition era. Not to be confused with a racketeer of the same name who exercised notorious control over the kosher chicken industry in the early 1930s.

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Eller, Emanuel—Son of Morris and an elected municipal judge. He used his judicial authority to keep many of his father’s criminal operatives out of police custody. Eller, Morris—The central political figure of Jewish Maxwell Street and the 20th Ward. As part of his political career, he assembled perhaps the largest predominantly Jewish gang in Chicago history, the 20th Ward gang, and he served as the conduit of political power for the Miller Brothers and many other Jewish and non-Jewish gangsters in the Big Bill Thompson era. Elrod, Arthur X.—Successor to Jacob Arvey as political boss of Jewish Lawndale. His own criminal ties were much more direct, as evidenced by his reported approval of the murder of Willie Tarsch and his serving as a payoff man for Lenny Patrick in the late 1940s. Factor, Jake “the Barber”—International swindler with connections to the Syndicate. He’s most notorious for claiming to be kidnapped by the Roger Touhy gang. Most histories regard his testimony as fabricated as part of a successful plan by Murray Humphreys to send Touhy to prison. Giancana, Sam—Prominent Syndicate boss of the 1960s. Glazier, Benjamin—Partner of Benny Zuckerman in Jewish Lawndale organized crime of the early 1940s. Died of a heart attack on hearing the news of Zuckerman’s murder. Glick, Herman—Small-time gambler and hoodlum in 1930s Jewish Lawndale. Victim of Lenny Patrick’s first murder. Granady, Octavius—African American politician from the 20th Ward. Morris Eller campaign operatives murdered him during the 1928 election. Guzik, Alma—Sister-in-law of Jack. She and her husband Harry were convicted of “white slavery” prostitution in 1921, but Illinois Governor Len Small pardoned them before they began their sentence. Guzik, Harry—Older brother of Jack and regarded as one of the central figures in the vice confederation of the pre-Prohibition era. Guzik, Jack—Likely the most consequential Jewish gangster in Chicago history. He helped bring elements of 1st Ward vice operations into the Syndicate, proved an early mentor and friend to Al Capone, and established the template for the Outfit’s highly effective “Connection guys.” Hadesman, Charles “Chick”—Rival of the Miller Brothers, he was the intended target when Max Miller and Samuel Friedman killed Abe Rubin in Max Eisen’s Humboldt Square saloon in 1922.

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Harrison, Carter, Jr.—Democratic mayor of Chicago from 1897–1905 and 1911–15, he maintained power by balancing anticrime reformists with organized criminals like Hinky-Dink Kenna who agreed to limit their activities to the 1st Ward Levee district. Toward the end of his tenure, he attempted to “close the Levee,” thereby driving crime to other neighborhoods, Maxwell Street among them. Humphreys, Murray—American-born to Welsh parents, he was regarded, alongside Jack Guzik and Gus Alex, as overseer of the “connections” that made citywide Outfit protection possible. Kenna, Mike “Hinky-Dink”—1st Ward politician who, with his partner “Bathhouse” John Coughlin, oversaw corruption and organized crime links from the 1880s into the Syndicate-era of the 1930s. Korshak, Marshall—Brother of Sidney and longtime political figure from Chicago’s South Side. Korshak, Sidney—Shadowy figure long reputed to be the Chicago Outfit’s representative in Los Angeles and Las Vegas. Krotish, Harry—Gambling rival murdered by Lenny Patrick in 1948. During Patrick’s testimony against Gus Alex in 1992, defense attorneys referred to him as “Harry the Horse,” confusing Patrick, who began joking about it. Larman, Frank—Owner of a notorious Maxwell Street gambling club in the 1910s. LaValley, James—Member of Lenny Patrick’s crew in the middle and late 1980s. He provided much of the information that compromised Mario Rainone. Levin, Hymie “Loud Mouth”—A noted Syndicate Loop gambling figure throughout the 1950s, apparently answering to Jack Guzik. Luciano, Charles “Lucky”—New York Sicilian American gangster credited with establishing “the Commission” system of five-family organized-crime confederation in the 1930s. Lufman, Eugene “Yudie”—Longtime lieutenant for Lenny Patrick. His arrest in 1973 put pressure on Patrick to testify against Outfit higher-ups in 1974. Mangano, “Dago” Lawrence—Successful Prohibition-era Italian American gangster who, like Zuckerman, was murdered as part of the Syndicate’s mid-1940s consolidation campaign. Marcello, James—Outfit underboss of the late 1980s rumored to be in line to assume the top position. He received a twelve-year sentence as part of the Sam Carlisi trial where Lenny Patrick served as the principle witness, and he was subsequently imprisoned, likely for life, in the 2005 Family Secrets trial.

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McDonald, Mike Cassius—Acknowledged as the first significant organized-crime figure in the wake of the Great Fire of Chicago in 1871. Miller, Al—Miller brother involved in boxing and booze smuggling. Miller, Davey—Leader of the Miller brothers. Well-known boxing referee and gambling operator in the heart of Jewish Lawndale. Famous for his defense of Jews across the city. Miller, Davey “Yiddles”—An apparently Jewish member of the South Side Ragen’s Colts street gang in the 1910s and 1920s known for his violent racism and for having been a cellmate of Roger Touhy. Some biographers have confused him with Davey Miller, to whom he was not related. Miller, Harry—Miller brother and police sergeant. He was part of the attempt to kill Syndicate head Frank Nitti, apparently under orders from Mayor Anton Cermak. Miller, Hirschie—One of the Miller brothers and well known as a bootlegger and racketeer. Alongside Nails Morton, he famously shot two off-duty policemen in 1920. Miller, Max—Miller brother shot with Davey by Dean O’Banion in 1924. He was also charged with murder alongside Sailor Friedman and others. Moran, George “Bugs”—Leader of the North Side Gang at the time of the St. Valentine’s Day Massacre. Morton, Samuel “Nails”—A founder, alongside Dean O’Banion, of the North Side Gang as well as an associate of Hirschie Miller. His death in a horseback-riding accident in 1923 may have widened the gulf between O’Banion and the early Syndicate, of which the Millers were a part. Murphy, Eddie—Partner of Lenny Patrick and David Yaras who, having helped them in some of their early murders, was murdered by them in turn. Neistein, Bernard—Longtime precinct captain from the Jewish West Side. He candidly discussed bending the law, but he was not himself reputed to be linked to organized crime. Newberry, Ted—Associated with the North Side Gang throughout Prohibition, he accepted a Syndicate alliance after the gang was mostly overwhelmed. Anton Cermak hoped to elevate him to boss status in his attempt to have Frank Nitti killed. Nitti, Frank—Generally acknowledged as the head of the Syndicate from Al Capone’s 1932 conviction for tax evasion until he committed suicide in 1943 to escape arrest for extorting Hollywood studios. O’Banion, Dean—Founder of the North Side Gang, who would shoot Davey and Max Miller. His chafing against the agreements underlying Johnny Torrio’s

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confederation brought about the gangster war that killed him and culminated in the St. Valentine’s Day Massacre. Patrick, Leonard—The central figure in Chicago Jewish organized crime from the death of Benny Zuckerman in 1944 until he became a cooperating witness in the late 1980s. Patrick, Mike—Brother of Lenny and a longtime operator in Chicago organized crime. Portugese, Alex—Brother of Jules and apparent triggerman in the 1927 shooting of Benny Zuckerman. Portugese, Harry—Father of Jules and Syndicate-linked owner of a Maxwell Street pawnshop. Portugese, Jules—Dashing and eventually desperate Prohibition-era gangster and thief out of Maxwell Street. Ragen, James—Successor to Moses Annenberg as owner of the wire services transmitting necessary information for gambling operators. He was shot in 1946 by Lenny Patrick, David Yaras, and William Block. While he was recovering in the hospital, he died from mercury poisoning. Rainone, Mario—Top lieutenant of Lenny Patrick after the death of Leonard Yaras. His willingness to wear a wire delivered the recordings that gave prosecutors the leverage they needed to persuade Patrick to cooperate. When he subsequently changed his mind about cooperating himself, he became a defendant alongside Gus Alex in 1992. Ricca, Paul—Credited with being, alongside Tony Accardo, the highest-ranking member of the Syndicate from the death of Frank Nitti in 1943 until his own death in 1972. He was convicted of extorting Hollywood studios in 1943 but received parole in 1947 in part through the efforts of Jacob Arvey. Rosenberg, Michael—First significant political boss of Jewish Lawndale and reportedly the man for whom the 24th Ward was designed for electoral advantage. He died suddenly of natural causes in 1928 having already brought a young Jacob Arvey into the organization. Rosenberg, Moe—Brother and political successor to Michael. He was charged with tax evasion in 1933 and died before he could come to trial. Rosenthal, Frank “Lefty”—Onetime underling for David Yaras, he emerged as one of the most high-profile figures in the Syndicate’s operations in Las Vegas. He is the basis for the Robert DeNiro character Ace Rothstein in Casino. Schwartz, “Yankee”—Ex-boxer and newcomer to Chicago whom Dean O’Banion put forward as a potential figure to replace Davey Miller. He was with O’Banion when he shot the Miller brothers.

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Skidmore, William—Longtime partner of Julius Anixter in gambling and political operations. Spilotro, Tony—Outfit representative to Las Vegas in the 1980s where he partnered with Frank Rosenthal. He is the basis for Nicky Santoro, played by Joe Pesci in Casino. Tarsch, Willie—Also known as “Kolatch” or “Galatz,” he was a lieutenant of Benny Zuckerman who persisted in fending off the Syndicate after Zuckerman’s death. Lenny Patrick later confessed in court to having had a hand in his murder. Thompson, William “Big Bill”—Republican mayor of Chicago from 1915–23 and again from 1927–31. He was notoriously connected to the Syndicate, permitting his allies, such as Morris Eller, to sell gambling and booze “concessions” across the city. Torrio, Johnny—Boss of the Italian-dominated gang that would come to be headed by Al Capone. He is credited with outlining the confederation model that created the Syndicate. Touhy, Roger—Boss of a gang that became prominent after the St. Valentine’s Day Massacre and allied with Jack Zuta, Joe Aiello, and remnants of the North Side Gang. He spent most of his adult life in prison on false charges that he kidnapped Jake “the Barber” Factor, and then he was murdered within weeks of his release. Vogel, Eddie—Longtime gambling figure who began in Cicero and eventually rose to high Syndicate rank. According to a series of ledgers Jack Guzik inadvertently allowed to fall into the Tribune’s hands, he was one of the highest-earning gangsters of the early 1940s. Weiss, Hymie—Polish American racketeer and bootlegger who succeeded Dean O’Banion as boss of the North Side Gang. Yaras, David—Partners with Lenny Patrick in organized crime operations in Chicago, Miami, and elsewhere. With Patrick and as part of other teams, he was one of the most prolific Outfit killers from the 1940s to the 1960s. Yaras, Leonard—Son of David, lieutenant to Lenny Patrick, and regarded as a rising power in the Outfit of the early 1980s. He was murdered in 1985. Yaras, Ronald—Son of David and his lieutenant in labor activities. Murdered in 1974 soon after his father’s death. Zuckerman, Benjamin “Zukie the Bookie”—As a protégé of Julius Anixter and as a political figure, bootlegger, gambler, and slugger in his own right, he emerged as the boss of the last independent predominantly Jewish gang in Chicago history. His 1944 murder marked the moment the Syndicate took over Jewish Lawndale.

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Zuta, Jack—Notorious pimp and gang leader who, already prominent in the early Prohibition years, ultimately allied with the North Side Gang in the wake of the St. Valentine’s Day Massacre. His posthumous exposé of Chicago organized crime created a furor.

NOTE ON SOURCES

The work of writing this book has been one of remembering, of making a coherent narrative from the different, lost pieces of the history of the Chicago Jewish gangster. Before that, though, it was a matter of recollecting, of recovering as many of those pieces as possible. And that research took me in three distinct directions. First, I had the opportunity to talk with a number of people with firsthand memories of the gangsters I have written about. That included Judge Abraham Marovitz, Mickey “Soldier” Farr, Davey Miller’s daughter Sylvia Friedman, Al Miller’s son Sylvan Miller, my friends Bill Reilly, Nathan Kaplan—who undertook a project to record oral histories of people who remembered Davey Miller—and others through John Binder’s Merry Gangsters Literary Society such as Pops Panzco and Toni Giancana. Such stories gave me a glimpse into a Jewish Chicago that had vanished long before I came along. They often provided details I could never have found in other ways—how else could I have known that longtime Syndicate Loop gambling boss Hymie “Loudmouth” Levine pronounced his name “Luh-VEEN”—but in general they confirmed or elaborated conclusions I’d reached from other sources. Other contemporary researchers, most memorably Robert Lacey and Rose Keefe, have overturned decades of popular perception by relying on oral histories from onetime insiders, but I never had such good fortune. Chris Gair filled in crucial gaps about the end of Lenny Patrick’s career, but otherwise the interviews I conducted gave more color than foundation. It’s perhaps ironic then, given that my mother’s family was so central to the early Jewish gangster world, that, even from the beginning, I relied primarily on written material. I’ve noted throughout this work the many excellent histories of Chicago gangsters and Jewish gangsters of other cities. I depended on many of those books to get oriented to my study, and they often led me to source material that allowed me to dig even deeper, to see the ways observers of the time understood the implications of the gangster. Al Capone’s world drew lots of technicolor attention, of course, but it also provided the real-world material for the invention of one kind of modern sociology. The sociologists of the University of Chicago, who were arguably the most influential thinkers in their discipline, studied the neighborhoods and political webs of the gangster and produced not simply academic studies but also a number of consequential government reports. John

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Landesco’s Illinois Crime Survey is the most famous and most influential of those, but the same professors and their students produced the studies that underlay the twelve-volume federal Wickersham Commission report as well as much of the anti-organized–crime legislation of the era. As an academic myself, I can’t help but feel a bit of wonder at recounting that Frederick Thrasher discussed the Miller brothers on page one, issue one, of the 1925 inaugural volume of Social Science, a journal that remains extant almost a century later. As part of that same effort of turning to the written reports of the era, I was fortunate to find my way to a number of archival sources. Dan Sharon, the longtime reference librarian at the Asher Library of the Spertus Institute, made it a point for several years to call my attention to anything Jewish gangster–related that came across his desk. My friend and co-author Walter Roth, whose early enthusiasm helped push me into the project, managed to provide Spertus with a photocopy of a scrapbook that Davey Miller put together from his career, collecting materials that otherwise would have remained private. At the Chicago Historical Society, I found useful papers from Jacob Arvey and Luis Kutner, who served as William Drury’s attorney, allowing me to fill in much of what I was missing on the political history surrounding the Outfit’s rise to monopoly status in Chicago crime. I have been fortunate as well to uncover a number of arrest and trial records. It’s remarkable to read affidavits from “concerned citizens” offering testimony to help overturn the murder conviction of my grandfather’s co-defendant, Sailor Friedman. Through Freedom of Information Act requests, I obtained hundreds of pages of FBI files that offered many of the details in the long careers of Lenny Patrick and Davey Yaras. And, thanks to the help of my cousin Steve Miller and a grant from the University of Scranton, I was able to read and re-read the dramatic transcript of Lenny Patrick’s testimony against Gus Alex. I have to reserve a special thanks to the Chicago Crime Commission for its staggering archival collection. For those unaware of its history, the Commission began as a citizen-led effort to collect material on criminals during the Prohibition era. Trusting neither the police nor the courts, it sent its investigators to take careful notes on trials and to surveil criminal haunts. Unlikely as it sounds, they actually assigned confidential observers to go into Davey Miller and Benny Zuckerman’s restaurants, providing detailed notes on who was working and who was eating. It’s the closest I can imagine to being able to stroll into those places myself. The Commission’s work began with a general distrust of the lower-class immigrant world that produced my family, but it remained committed to a belief in law, and it remains a remarkable, multigenerational effort at assuring a crime-free city

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for all Chicagoans. As such, I have felt a kinship with Frank Loesch and Virgil Peterson—both longtime directors who died decades before I began my work—up through more recent staffers such as Jeanette Callaway, Wayne Johnson, Elisabeth Saffell, and Andrew Henning, who have all taken time to help me navigate the labyrinthine files that they alone possess. Perhaps the most useful direction of my research, however, has been the legwork of digging through old newspapers. The earliest work I did consisted of spending hours in front of microfilm at the Chicago Public Library. Thirty years ago, I’d determine the date of some incident—whether Dean O’Banion’s shooting my grandfather; Hirschie Miller and Nails Morton killing two police officers at the Pekin Inn; or Harry Miller helping to shoot Frank Nitti—and then I’d look for the coverage of it over the following several days in each of Chicago’s seven or eight newspapers. The competition among those long-ago reporters had each reaching for something the others didn’t have, and I’d often find intriguing theories or background information in the final paragraphs of a story. That process got a lot easier roughly fifteen years ago when the Tribune released its first online index. Suddenly, I could look for a name or keyword and have the computer do in seconds what it had taken me days to do before. I could not take advantage of the other Chicago newspapers through that process—no one has yet indexed the Times, the American, or the Daily News—but I could check in the New York Times, and I could do it in off hours from home. In recent years, thanks largely to the searchable Newspapers.com national newspaper archive, I have been able to search for out-of-town and wire service reporting on the goings-on of the gangsters in Chicago, and that has restored my ability to contrast one newspaper’s coverage with another. From the first time my mother showed me The Joker Is Wild with its claim that Dean O’Banion killed my grandfather, I have been tantalized by each mention I have found of the gangsters who have come to comprise the story here. Beyond the range of oral history, archival, and newspaper sources, I’ve found traces as well in old magazines and memoirs, references so unlikely that it’s seemed simply chance that I’ve stumbled upon them. With that, I imagine there are still bits and pieces of the history I have yet to find. Researching this book has been a thirty-year project, and I imagine I will continue to uncover fresh pieces that have somehow survived.

NOTES

Notes to Introduction 1. The paperback edition of Art Cohn’s The Joker is Wild, published in 1957 to coincide with the release of the motion picture starring Frank Sinatra and Mitzi Gaynor, reported, erroneously as it turned out, that my grandfather had been shot and killed by Dean O’Banion. It turns out that the hardcover 1955 release had the correct story: while O’Banion did shoot my grandfather, the bullet hit his belt buckle and did no damage. Instead, it was his brother, Davey Miller, who was seriously wounded. In any case, my mother’s coming across the reference in the paperback started me on my research. For a fuller account of that story, see chapter 4, “Landing in Lawndale.” 2. See chapter 6 for a fuller discussion of that point. 3. Irving Cutler, The Jews of Chicago: From Shtetl to Suburb (Urbana: University of Illinois Press, 1996), 223. 4. Albert Fried, The Rise and Fall of the Jewish Gangster in America (New York: Holt, Rinehard and Winston, 1980), 105–6. Other significant histories of the Jewish gangster available in that era included Robert Lacey’s exceptional Little Man: Meyer Lansky and the Gangster Life (New York: Little, Brown, 1991); Hank Messick’s work on Cleveland, The Silent Syndicate (New York: MacMillan, 1967); Paul Kavieff ’s work on Detroit, The Purple Gang: Organized Crime in Detroit, 1910–1945 (Fort Lee, NJ: Barricade Books, 2000); Mark Stuart’s biography of Longy Zwillman, Gangster #2: Longy Zwillman, the Man Who Invented Organized Crime (Secaucus, NJ: Lyle Stuart, 1985); and Dean Jenning’s We Only Kill Each Other: The Life and Bad Times of Bugsy Siegel (New York: Prentice-Hall, 1967). 5. See Laurence Bergreen, Capone: The Man and the Era (New York: Simon and Schuster, 1994), 86, for a discussion of how contemporary observers regarded the emerging Syndicate as a kind of “trust” as early as 1919. 6. For a full account of McDonald’s career, see Herbert Asbury, Gem of the Prairie: An Informal History of the Chicago Underworld (Garden City, NY: Garden City Publishing, 1942), 142–60. For a capsule account of McDonald’s rise as the city’s criminal-gambling boss, see Richard Lindberg, Chicago By Gaslight: A History of Chicago’s Netherworld, 1880–1920 (Chicago: Academy Chicago, 1996), 13, 47–51, and Steven A. Riess, “Horse Racing In Chicago, 1883–1894: The Interplay of Class, Politics, and Organized Crime,” in Steven A. Riess and Gerald R. Gems, The Chicago Sports Reader: 100 Years of Sports in the Windy City (Urbana, IL: University of Illinois Press, 2009), 60–63. In a historical oddity, the aging McDonald fell in love in the late 1890s with a younger Jewish woman, Dora Feldman, married her in a Jewish ceremony, and may have converted to Judaism for her sake (see Walter Roth, Looking Backward: True Stories from Chicago’s Jewish Past [Chicago: Academy Chicago, 2002], 216–17). 7. For the fullest account of Kenna and Coughlin’s rise to criminal authority, see Lloyd Wendt and Herman Kogan, Lords of the Levee: The Story of Bathhouse John and Hinky Dink (Garden City: NY: Garden City Publishing, 1944). For the link between the pair and Jim Colosimo, founder of the Torrio-Capone gang, see Bergreen, Capone, 80–1. 8. See chapter 2 here for a more sustained discussion of the Syndicate’s rise under Torrio and Capone. 9. Cutler, Jews of Chicago, 211.

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10. Ibid., 238–69. 11. Some of the leading names of that academic group include John Landesco, Frederic Thrasher, Robert E. Park, and Clifford Shaw. Landesco and Thrasher in particular focused on Chicago gangland, with Landesco producing his Illinois Crime Survey, certainly the most authoritative contemporary overview of Chicago organized crime in the 1920s—complete with a geography of the city’s criminal domains—and with Thrasher writing The Gang, a sociological study that theorized the ways in which gangs flourished in the “interstitial” areas and neighborhoods where traditional authority failed to reach. 12. Daniel Bell, “Crime as an American Way of Life,” in The End of Ideology: On the Exhaustion of Political Ideas in the Fifties, rev. ed. (New York: Free Press, 1962), 146–48. 13. James M. O’Kane, The Crooked Ladder: Gangsters, Ethnicity, and the American Dream (New Brunswick, NJ: Transaction, 1992), 4–6. 14. Cutler, Jews of Chicago, 193.

Notes to Chapter 1 1. See “Records Show Payoffs from County Towns,” Tribune, October 26, 1941, for a report that the traditional “tax” for satellite operations like Zuckerman’s was 25 percent of the take. See “Gambling Jury Gets Officials’ ‘I Don’t Know,’” Tribune, January 18, 1944, for the claim that the Syndicate had announced plans to double it to 50 percent. 2. Frank Cipriani, “Gambler Killed; Pal Dies,” Tribune, January 15, 1944. 3. “Hunt 3 Callers on Zuckerman Before Slaying,” Tribune, January 16, 1944. 4. “‘Alky’ Dealer Shot Down as He Enters Home,” Tribune, March 16, 1927. 5. The narrative of Zuckerman’s murder commingles details from Frank Cipriani, “Gambler Killed; Pal Dies,” Tribune, January 15, 1944; and “Partner Dies Hearing News,” Chicago Sun, January 15, 1944. 6. CCC File 65–73, dated February 18, 1944, p. 2. 7. “Jack Guzik Now is No. 1 Man of Gang Overlords,” Tribune, October 25, 1941. 8. See Bergreen, Capone, 104–10; and Robert Schoenberg, Mr. Capone: The Real—and Complete—Story of Al Capone (New York: William Morrow, 1992), 97–99. 9. John W. Fountain, “Town President is Convicted in Scheme to Steal $12 Million,” New York Times, August 24, 2002. 10. “Partner Dies Hearing News,” Chicago Sun, January 15, 1944. 11. Ibid. 12. Orville Dwyer, “Disclose Ragen Told Sheriff of Gang-Run Books,” Tribune, July 6, 1946. 13. Art Petacque, “Touch of Class Marks the End of Rags-to-Riches Career,” Sun-Times, October 20, 1950. 14. CCC memo, May 7, 1945. 15. CCC memos, April 17, 1945, and April 24, 1945. 16. CCC memo, May 7, 1945. 17. Patrick testimony in Alex trial, 927. 18. “Janitor Dies in Battle for Stolen Tools,” Chicago Times, undated clipping from CCC file on Tarsch. 19. “Seek Gambling Link as Clew in Gang Slaying,” Tribune, June 10, 1948. 20. CCC memo, May 7, 1945. 21. Ovid Demaris, Captive City: Chicago in Chains (Secaucus, NJ: Lyle Stuart, 1969), 125. See also CCC memos, April 9, 1945, and May 7, 1945. 22. “Gambling Aid to ‘Zookie’ Slain” Chicago Times, April 4, 1945. 23. For the narrative of Tarsch’s murder, I have drawn on reports from “Gambler Slain from Ambush on West Side,” Tribune, April 7, 1945; and “Tell Gaming Killing ‘Inside,’” Chicago American, April 10, 1945. 24. “Kill Gambler in Ambush,” American, April 7, 1945.

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25. Patrick would admit to having helped kill Tarsch in his 1992 testimony against Gus Alex.

Notes to Chapter 2 1. Armitage Trail, Scarface (London: Xanadu Publications, 1990 [1930]). 2. See Ben Hecht’s A Child of the Century (New York: Donald A. Fine, 1985 [1954]), 486–87. 3. David E. Ruth, Inventing the Public Enemy: The Gangster in Popular Culture, 1918–1934 (Chicago: University of Chicago Press, 1996), 6. 4. David Ruth explains that success was largely the result of capitalizing on a series of cultural anxieties. As true as that is, it came at the expense of a history that accurately reflected the particular rise of Al Capone or the more general rise of increasingly sophisticated, corporate-style organized crime. 5. For Torrio’s central role in that process, see either of the Capone biographies competing for definitive, Schoenberg’s Mr. Capone, 67–84, or Bergreen’s Capone, 37–38 and 82–90. 6. For an analysis of the structure of the tendency toward greater sophistication in criminal organization, see Humbert S. Nelli, The Business of Crime: Italians and Syndicate Crime in the United States (Chicago: University of Chicago Press, 1981), 162–68. For the general idea that organized crime is fundamentally a matter of organization—or confederation—over the more common narrative of conquest, see Alan Block’s seminal East Side-West Side: Organizing Crime in New York, 1930–1950 (New Brunswick, NJ: Transaction, 1995 [1980]), esp. 129–30, but with an analysis running throughout. See Robert M. Lombardo’s Organized Crime in Chicago: Beyond the Mafia (Urbana: University of Illinois Press, 2013) for a more Chicago-centered study of the phenomenon, esp. 1–8. 7. For coverage of the June 1920 conference, convened at the Brevoort Hotel by Torrio, see “Cops Land in Jail; Freed on Bail,” Tribune, May 20, 1924, Landesco crime survey (without quite the detail), 97. See also John Binder, Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago during Prohibition (Amherst, NY: Prometheus Books, 2017), 120. 8. Frederic M. Thrasher, The Gang: A Study of 1,313 Gans in Chicago (Chicago: University of Chicago Press, 1927 [1936]), xxi. 9. Roy J. Gibbons, “Chicago’s Murders Reveal Underworld Constantly at War,” NEA/WilkesBarre Times Leader, October 16, 1926; and “Gangland Lays Its Guns Aside; Peace Declared,” Tribune, October 21, 1926. 10. Binder, Beer Wars, 199–200, 207. 11. John Lyle, The Dry Lawless Years (New York: Prentice-Hall, 1960), 18–20. 12. Ironically, another book published in 1929, the same year as Trail’s Scarface, told the story of confederation in remarkable detail. John Landesco’s Illinois Crime Survey—republished in 1969 as Organized Crime in Chicago: Part III of the Illinois Crime Survey, 1929 (Chicago: University of Chicago Press)—remains one of the central reference works for the period even in the face of dozens of well-researched histories written since. 13. Binder, Beer Wars, 148–50. 14. See Alson Smith, Syndicate City: The Chicago Crime Cartel and What to Do about It (Chicago: Henry Regnery, 1954), 11–14. 15. At least two newspaper stories from the late 1940s claim that Zuckerman was under pressure to pay an unprecedented cut to the “Italians.” See “Lay Zuckerman Killing to Gang Greed for ‘Cut,’” Tribune, January 18, 1944; and “Tell Gaming Killing ‘Inside,’” Chicago American, April 10, 1945. 16. One substantial start toward that story comes in Gus Russo’s The Outfit: The Role of Chicago’s Underworld in Shaping Modern America (New York, Bloomsbury, 2003), an ambitious 500-plus-page effort to dramatize the changed nature of Chicago organized crime in the second half of the twentieth century. 17. Cutler, Jews of Chicago, 58.

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18. See ibid., 61, for a sociologist’s observation that, in 1891, “there is only one saloon to ten in the other districts.” 19. The definitive history of the Levee is Wendt and Kogan’s Lords of the Levee. See esp. 24–27. 20. Richard Lindberg, Gangland Chicago: Criminality and Lawlessness in the Windy City (Lanham, MD: Rowman and Littlefield, 2016), 62–66. 21. Hirschie’s age extrapolated from his obituary, “Unlike Old Pals, Hirschie Miller Has Quiet Death,” Tribune, July 13, 1939. 22. “News of the Day Concerning Chicago,” Chicago Day Book, February 22, 1915. 23. Quoted in “Demand M’Weeny Act on Gambling,” Tribune, July 20, 1913. 24. For a history of the philosophical and marketing reasons behind the Tribune’s embrace of the progressive Republican movement and its call for better government in the early 1910s— coinciding with the ascent of Robert R. McCormick as publisher—see Lloyd Wendt, The Chicago Tribune: The Rise of a Great American Newspaper (Chicago: Rand McNally, 1979), 375–93. For a particular look at McCormick’s political calculus just before the time of the Tribune raids, see Richard Norton Smith, The Colonel: The Life and Legend of Robert R. McCormick, 1880–1955 (Boston: Houghton-Mifflin, 1997), 140–44. 25. “Hoyne Indicts a ‘Tribune’ Man,” Tribune, July 19, 1913; also Lindberg, Gangland Chicago, 139–40. 26. Stuss was a variation of the once very popular game of faro where players have the opportunity to place bets on the turn of a playing card. According to Herbert Asbury, it developed on New York’s Lower East Side where it was frequently the game of choice in games controlled by such early Jewish gangsters as Monk Eastman, Kid Twist, and Johnny Spanish. It had a particular vogue among Jewish immigrants of the period and was often known as “Jewish Faro.” Herbert Asbury, Sucker’s Progress (Montclair, NJ: Patterson Smith Reprint Series in Criminology, Law Enforcement, and Social Problems, 1969 [1938]), 18. 27. “Demand M’Weeny Act on Gambling,” Tribune, July 20, 1913. 28. “Squint,” it turns out, was the nickname for Nathan Salintzky, apparently a longtime figure in the Runyonesque world of Chicago’s illegal gambling. See “Hunt Policeman As Gangster Is Found Wounded,” Tribune, June 22, 1924. 29. “Demand M’Weeny Act on Gambling,” Tribune, July 20, 1913. 30. “Coffee Sippers Get Laugh,” Tribune, April 19, 1914. 31. Maureen McKernan, “In $10,000 Casket Dean Lies in State,” Tribune, November 13, 1924. 32. “Four Men Nabbed and 140 Gallons of Wine Retaken,” Tribune, October 26, 1924. 33. Binder, Beer Wars, 293 and 113–15; also “Link McErlane to Mystery of Charred Auto,” Tribune, October 13, 1931. 34. “Prisoners’ Whistles Brought Liquor,” New York Times, July 24, 1926; “Who’s Got the Bottle? Jail’s Favorite Game,” Tribune, July 24, 1926. 35. Robert Schoenberg, Mr. Capone, 118, siding with the general consensus, declares it was Frank Yale accompanied by John Scalise and Albert Anselmi; Laurence Bergreen, Capone, 135, insists it was Mike Genna accompanied by Scalise and Anselmi; George Murray, The Legacy of Al Capone: Portraits and Annals of Chicago’s Public Enemies (New York: G. P. Putnam’s, 1975), 65, goes with James Genna, Carmen Vacco, and Pete Gusenberg. 36. Maureen McKernan, “In $10,000 Casket Dean Lies in State,” Tribune, November 13, 1924, “Rid City of Gunmen—Dever,” Tribune, November 14, 1924. 37. Maureen McKernan, “In $10,000 Casket Dean Lies in State,” Tribune, November 13, 1924. 38. Chief ’s Men Make Raid,” Tribune, March 15, 1915. 39. See Cutler, Jews of Chicago, 221–25. 40. “Slain Portugese is Identified in $80,000 Holdup,” Tribune, July 15, 1926. 41. “Booze Hijacked, 5 Cops Victims, Is Murder Story,” Tribune, July 16, 1926. 42. “Kill 1, 3 Shot in Crime Drive,” Tribune, January 17, 1925. 43. “Booze Hijacked, 5 Cops Victims, Is Murder Story,” Tribune, July 16, 1926.

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44. “Nab $300,000 Gem Robber in Loop Crowd,” Tribune, December 18, 1925. 45. “Portugese Gets Year in Jail for Carrying Gun,” Tribune, December 20, 1925. 46. “Slain Portugese Is Identified in $80,000 Holdup,” Tribune, July 15, 1926. 47. “Jules Portugese, Gunman, ‘Taken for a Ride,’” Tribune, July 14, 1926. 48. “Slain Portugese Is Identified in $80,000 Holdup,” Tribune, July 15, 1926. 49. David Ruth, Inventing the Public Enemy, 12. 50. “Hold Service for Portugese,” Chicago Herald-Examiner, July 17, 1926. 51. See “Four Men Nabbed and 140 Gallons of Wine Retaken,” Tribune, October 26, 1924, for address. See “Revokes License of Gambling Den Scene of Shooting,” Tribune, July 16, 1913, for the district crackdown; Portugese’s place is not specifically mentioned.

Notes to Chapter 3 1. The first report in Patrick’s FBI file is dated January 14, 1958. 2. See William Roemer, Man against the Mob: The Inside Story of How the FBI Cracked the Chicago Mob by the Agent Who Led the Attack (New York: Donald I. Fine, 1989), 22–25; and Lacey, Little Man, 173, 202, 282. 3. Roemer, Man against the Mob, 22–31. 4. Author’s personal observation. I was able to visit Accardo’s home after the subsequent owners, capitalizing on its notoriety, conducted an estate sale. The table was still in place. 5. Robert Wiedrich, “A New House Has Accardo All Excited,” Tribune, November 7, 1963. 6. William Roemer, Accardo: The Genuine Godfather (New York: Dutton, 1995), 13. Tribune reports “Witness Sees Silencers in Corbin Killing” (July 22, 1966), and “Police Chase Evidence in Corbin Killing” (July 23, 1966), confirm some of the details of the story as Roemer records it. 7. George Bliss, “Police Clean Up at Luxor Baths,” Tribune, February 24, 1974. 8. “Morris Lasky, Mob Figure, Held in Gambling Raid Again,” Tribune, October 15, 1970. 9. Off-track betting was legalized in New York in 1970; see Vincent Butler, “Off-Track Betting Legalized by New York’s Legislature,” New York Times, April 21, 1970. It remained illegal in Illinois until 1987; see Neil Milbert, “Off-track Betting Moves Out of Gate,” Tribune, July 1, 1987. 10. John O’Brien, “Bet Room Scratched; Police Too,” Tribune, September 10, 1970. 11. Bob Wiedrich, “Lenny Patrick: Oh, What He Could Tell,” Tribune, February 3, 1974. 12. In later years, as his testimony in the Alex trial made clear, Patrick used that reputation as part of a series of extortions. He’d send some of his crew to threaten a potential victim, usually someone Patrick had known a long time, demanding a substantial payment. The victim would turn to Patrick for help, and Patrick, pretending to be an intermediary, would “broker” a lower payment, never revealing he was the one behind the whole scheme. (The interview with Chris Gair helped clarify that scheme.) 13. George Bliss, “Investigators Report Uncovering Payoff Center for Shakedowns,” Tribune, March 11, 1973. 14. “Police Seize 17 During Raid on N. Side Lounge,” Tribune, September 10, 1966. 15. Bob Wiedrich, “Efforts Fail to Close Sodom of Uptown,” Tribune, April 21, 1974. 16. Bob Wiedrich, “More Corruption That Went Unseen,” Tribune, December 19, 1973. 17. Irving Cutler describes the rapid shift in greater Lawndale’s population from predominantly Jewish to predominantly African American in his demographic overview on at 231–33. For the corresponding rise in the Jewish population of Rogers Park, see Cutler, Jews of Chicago, 244–46. 18. Alex testimony, 1182. 19. See Cutler’s Jews of Chicago, 244, “From 1930 to 1960, the Jewish population of Rogers Park more than doubled to about 22,000.” And at 249, “In the 1950s, the Jewish population of West Rogers park [also known as West Ridge] quadrupled, and in 1963 it reached an estimated 48,000 or about three-fourths of the total population.”

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20. See Gary Rivlin’s “The Night Chicago Burned,” [Chicago] Reader, August 25, 1988, , retrieved July 25, 2017; see also Patrick T. Reardon, “West Side’s Sad Story,” Tribune, August 9, 1992. 21. FBI report; also Demaris, Captive City, 348. 22. See Alex testimony, 1686. 23. “Organized Crime in Chicago,” CCC report, 26. 24. See Alex testimony, 1288, 1292–93. 25. Ibid., 988. 26. Roemer, Man against the Mob, 168, “For decades Patrick fulfilled the role of a capo, taking charge of gambling activity, first in Lawndale and then in Rogers Park.” 27. See Jeremy Martin, “‘Squares’ Become Well Rounded,” Doc’s Sports Journal 35 (2005): 11–12. The article is archived online at . 28. Bill Granger and Lori Granger, Lords of the Last Machine: The Story of Politics in Chicago (New York: Random House, 1987), 179–80, 199. 29. Alex testimony, 938, 940. 30. See Milton Rakove interview with Abner Mikva in Rakove, We Don’t Want Nobody Nobody Sent: An Oral History of the Daley Years (Bloomington: Indiana University Press, 1979), 318. 31. As Roger Biles described it, “For most of the Daley years, council business proceeded under the crisp leadership of the mayor’s floor leader, thirty-first ward alderman Thomas Keane; after Keane’s conviction for mail fraud in 1974, eleventh ward alderman Michael Bilandic performed the task. The city council rarely functioned as a deliberative body, for department heads framed legislation in consultation with the mayor long before introducing bills in the legislative process.” See Roger Biles, Richard J. Daley (Dekalb: Northern Illinois University Press, 1995) 57. 32. See Biles, Richard J. Daley, 199–200. 33. Patrick FBI file, reports dated December 31, 1970, Cover page D, and April 19, 1971, p. 2. 34. Patrick FBI file, report dated December 31, 1970, Cover page B. 35. Alex testimony, 937. 36. Stephen Brill, The Teamsters (New York: Simon and Schuster, 1978), 24–25; Gus Russo, Supermob: How Sidney Korshak and Associates Controlled America (New York: Bloomsbury, 2006), 166–67, 309, 375. 37. Roemer, Accardo, 348–51; Pileggi, Casino: Love and Honor in Las Vegas (New York: Simon and Schuster, 1995), 336–37. Dorfman is generally the basis for the character played by Alan King in the 1995 film Casino. 38. Alex testimony, 950–51. 39. Demaris, Captive City, 348. 40. Alex testimony, 950–51. 41. Alex testimony, 952–54, 1294–96. 42. Bob Wiedrich, “Lenny Patrick: Oh, What He Could Tell,” Tribune, February 3, 1974. 43. Patrick FBI file, memo to acting director, May 16, 1973. Original filed in 165–3532–52. 44. Bob Wiedrich, “The Old Gray Mob, It Aint What It Used to Be,” Tribune, April 21, 1974. 45. Roemer, Man against the Mob, 29–30, 94, 101. 46. “Yaras,” death notice, Miami Daily News, January 7, 1974. 47. Bob Wiedrich, “Mobster’s Empire a Humpty Dumpty,” Tribune, January 13, 1974. 48. “Mob Aide Seized on Gun Charge,” Tribune, January 26, 1971; “Rip Steel Door to Rout 200 in Handbook Raid,” Tribune, February 16, 1955; “Police Arrest 14 in Gambling at Restaurant,” Tribune, April 3, 1963; “100 Stage Huge Policy Raids,” Tribune, April 23, 1964. 49. Patrick FBI file, report dated May 23, 1973, p. 2. 50. Bob Wiedrich, “Mob Picks ‘Statesman’ to Coll Heat of Quiz,” Tribune, February 18, 1973. 51. Bob Wiedrich, “Finally, Somebody’s After the Real Rot,” Tribune, September 30, 1973. 52. Alex testimony, 957–8 and 1188. 53. Patrick FBI file, report dated March 21, 1975 p. 6.

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54. “Cop Threat on Mobster Told,” Tribune, September 10, 1975. In the unsuccessful appeal of his sentence, Patrick would cite O’Hara’s intimidation as a reason to vacate his conviction on contempt charges. 55. Rudolph Unger, “2 Tax Counts Dropped in Cop’s Trial,” Tribune, June 12, 1975; and Richard Phillips, “Hood Leonard Patrick Convicted of Contempt,” Tribune, September 11, 1975. 56. Alex testimony, 963.

Notes to Chapter 4 1. William Shepherd, “How to Make a Gangster.” Collier’s 92, no. 10 (September 2, 1933): 12. 2. Sylvia Friedman oral history conducted by Nathan Kaplan. 3. “Davey Miller Funeral Rites Scheduled Monday,” Tribune, February 12, 1960; his daughter, Sylvia Friedman, claimed Miller was unsure of his own birth year. 4. See death notice for Al Miller, Tribune, February 16, 1947. 5. Oral history with Stanley Friedman, Miller’s grandson, conducted by Nathan Kaplan, November 10, 1988, p. 7–8. 6. Walter H. Eckersall, “Chicago Selects Pugilistic Squad for Amateur Meet,” Tribune, January 4, 1914 (featuring a photo of Miller); and “Select Seven Local Boxers for Fights at Cleveland,” Inter-Ocean, January 4, 1914. 7. For one measure of the extent of Miller’s reputation as a referee, see the celebrity-laden tribute held on March 23, 1950, when he announced he would be retiring. “Miller Feted for 35 Years as Referee,” Tribune, March 24, 1950. See also famed sports columnist Arch Ward’s tribute, “In the Wake of the News,” Tribune, December 29, 1949. 8. Walter Eckersall, “404 Amateurs to Fight for Golden Gloves,” Tribune, March 4, 1928; Miller was a referee in the original 1928 contest and continued refereeing throughout the tournament until the early 1950s. 9. See Barney Ross and Martin Abramson, No Man Stands Alone: The True Story of Barney Ross (Philadelphia: Lippincott, 1957), 87, 98, 109–10; Douglas Century, Barney Ross (New York: Nextbook, 2006), 18, 23; and Damon Runyon, “Ross’s First Pilot Picks Him to Win,” Pittsburgh Post-Gazette, September 5, 1934. 10. Damon Runyon, “Ross’s First Pilot Picks Him to Win,” Pittsburgh Post-Gazette, September 5, 1934. 11. Mike Conklin, “Odds & Ins,” Tribune, November 17, 1992. 12. See oral history of Larry Goldenberg, taken by Nathan Kaplan in packet dated March 1, 1989, for his recollection of the address. 13. Howard Carr, “Notes and Gossip of the Squared Circle,” Inter-Ocean, January 18, 1913. 14. “Mayor Revokes Bar Licenses,” Tribune, September 24, 1915; and “News of the Day Concerning Chicago,” [Chicago] Day Book, September 29, 1915. 15. “News of the Day Concerning Chicago,” [Chicago] Day Book, February 22, 1915. 16. “Chief ’s Men Make Raid,” Tribune, March 15, 1915. 17. “Daily Comment on People and Things,” [Chicago] Day Book, May 24, 1913. 18. “Twelve Taken in $150,000 Whisky Raid,” Chicago Daily News, August 24, 1920. 19. Frederic M. Thrasher, “Gangland,” Social Science 1, no. 1 (Nov. 1925): 1. The full quote is “Through the newspapers the public has become aware of some of the master gangs like the O’Donnels, [sic] the Torrios, the Gennas, the Millers, and the Valley gang.” 20. Oral history with Abraham Marovitz conducted by Nathan Kaplan, in packet dated March 1, 1989, p. 3. 21. Oral history with Stanley Friedman, Miller’s grandson, conducted by Nathan Kaplan, November 10, 1988, p. 3. 22. Brenda Warner Rotzoll, “1913: Jews Stand Up to Bias,” in Adrienne Drell, Chicago SunTimes’s 20th Century Chicago: 100 Years, 100 Voices (Sports Publishing, 2000), 39. 23. Ann Friedman, “Life Among the Poles in Old South Chicago,” Chicago Jewish History 12, no. 4 (June 1989): 5.

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24. Cutler, Jews of Chicago, 223. 25. Oral history with Albert Epstein conducted by Nathan Kaplan, in packet dated March 1, 1989, pp. 1–2. 26. The ‘M’ of the restaurant’s name was for Miller. The ‘E’ was for his brother-in-law, Sam Edelstein. In similar fashion, the attached gym was called the Edmille Athletic Club. 27. Cutler, Jews of Chicago, 193 and 209. 28. Ibid., 209–10. 29. Ironically, the specific neighborhood known as Lawndale, or sometimes South Lawndale, had a less concentrated and smaller Jewish population than the adjacent neighborhoods to the north that formed greater Jewish Lawndale. See Alex Gottfried’s Boss Cermak of Chicago: A Study in Political Leadership (Seattle: University of Washington Press, 1962), 33–38, for a focus on the particular Bohemian nature of that community. 30. Cutler, Jews of Chicago, 211. 31. Ibid., 210. 32. William Shepherd. “How to Make a Gangster.” Collier’s 92, no. 10 (September 2, 1933): 12. 33. Oral history with Harry Shoub conducted by Nathan Kaplan, in packet dated March 1, 1989, p. 1. 34. Oral history with Sam Simon conducted by Nathan Kaplan, in packet dated March 1, 1989, pp. 1–2. 35. Oral history with Leon Sex conducted by Nathan Kaplan, in packet dated March 1, 1989, p. 1. 36. “Chicago Poles Could Not Stage a Pogrom Yesterday,” Chicago Daily Courier, June 6, 1919, archived online as part of the Newberry Library’s Foreign Language Press Survey at . 37. Thrasher, The Gang, 196. In the course of conducting his work, Thrasher pushed against the glamorization of the gangster to the point that he refused even to name the gangs he wrote about, giving them coded titles instead. Still, his description of the WWW’s as located “along Roosevelt Road” (14) and largely “composed of professional prize fighters” (214) makes it clear he’s referring to Davey Miller and his followers. 38. William Shepherd, “How to Make a Gangster,” Collier’s 92, no. 10 (September 2, 1933): 12–13. In some of the little historical attention that Miller has received, he has been unfairly tarnished as a racist. The origin of the confusion seems to be in John Kobler’s 1971 Capone: The Life and World of Al Capone (New York: Putnam’s), the first attempt to write a research biography of Capone. In his work, Kobler seems to have conflated a south-side figure named Davey “Yiddles” Miller, a member of the Ragen’s Colts gang that was implicated in the race riots of 1919. Yiddles—whose nickname seems almost certainly to have been assigned to him for being a rare Jew in that context—may have been the same person who remained a prominent pickpocket from the 1930s to the 1950s, or there may have been a third David Miller in Chicago crime circles of the period. See “Fined in Court,” Tribune, August 25, 1932, for a story and photo—showing a clearly different Davey Miller. See also Roger Touhy and Ray Brennan, The Stolen Years (Cleveland, OH: Pennington Press, 1959), 52, for an account of when Touhy and Yiddles were cellmates. Miller’s daughter Sylvia was adamant that her father was essentially color-blind, and in an oral history she gave to Nathan Kaplan, she told the story of how he was so moved by the plight of a young African American man that he brought him to live with the family for several weeks in the late 1920s (Nate Kaplan oral history with Sylvia Friedman, packet dated March 1, 1989. No clear page numbers given). 39. Cutler, Jews of Chicago, 224–25. 40. Gottfried, Boss Cermak, 336–43. 41. “Spiritual Poverty in Lawndale District,” Jewish Daily Courier, March 17, 1914, archived as part of the Newberry Library’s Foreign Language Press Survey at . 42. Beryl Satter, Family Properties: Race, Real Estate, and the Exploitation of Black Urban America (New York: Metropolitan Books, 2009), 3. 43. Cutler, Jews of Chicago, 211.

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44. Bea Kraus and Norman Schwartz, A Walk to Shul: Chicago Synagogues of Lawndale and Stops on the Way (Allegan Forest, MI: Priscilla Press, 2003), xiv. 45. “Gamblers Scared,” Tribune, November 27, 1921. 46. Ibid. 47. William Shepherd, “How to Make a Gangster,” Collier’s 92, no. 10 (September 2, 1933): 12–13. 48. Prizefighting was illegal in Illinois from 1869 to 1926 with boxing, even in its exhibition form, often prohibited as well (see Steven A. Riess, “Closing Down the Open City: The Demise of Boxing and Horse Racing in Chicago,” in Elliot J. Gorn, ed., Sports in Chicago, [Urbana: University of Illinois Press, 2008], 43–48), so Miller’s position as a gym owner and referee— often in other states where it was legal—put him already at a crossroads between licit and illicit enterprises. As an example of that shadowy economy, Barney Ross recalled that, when fighting in what were technically amateur fights at Miller’s Edmille gym at 3216 W. Roosevelt Road, he would often win “a box of shirts, sometimes ties or socks, sometimes a pair of shoes,” Ross and Abramson, No Man Stands Alone, 77) that he would then promptly sell at the Maxwell Street market. That is, Miller effectively paid Ross for fighting, but it was a laundered exchange. 49. Braddock would go on to win an unlikely late-career heavyweight title, earning him the nickname “Cinderella man,” which also served as the title of a 2005 bio-film starring Russell Crowe. Miller refereed his fight against Leo Lomski on January 17, 1930 (note: I take the dates for the following fights from the online resource boxrec.com, accessed March 18, 2018). 50. Miller refereed at least two of Carnera’s fights, against George Cook (July 29, 1930) and Bearcat Wright (July 17, 1930). 51. Lamotta would eventually become the subject of the famous 1980 Martin Scorsese/ Robert DeNiro film, Raging Bull. Miller refereed his fight against Bob Satterfield (September 12, 1946) at Wrigley Field. 52. Miller had a long, personal relationship with Leonard, who is consistently ranked among the greatest boxers of all time. The Davey Miller scrapbook at the Chicago Jewish Archives housed at the Spertus Institute contains a letter that Leonard wrote to Miller in 1930, trying to make up for a misunderstanding around the death of Miller’s brother Max in 1926. It seems Leonard had not acknowledged the death, and he wrote to Miller to explain that he had simply not heard the news. (Excerpts of the letter are included in Roth, Looking Backward, 225.) Miller refereed at least two of Leonard’s fights, against Rocky Kansas (July 4, 1922) and Pinky Mitchell (May 29, 1923) in a bout that unsuccessfully sought to overturn the ban on prizefighting in Illinois. (See “Boxing Killed in Chicago By Riot at Society Bout,” Tribune, May 31, 1923; and Jim Bowman, “How a Pioneer Fight Promoter Helped Knock Out Illinois’ Boxing Ban,” Tribune, May 6, 1984.) 53. Miller refereed five of Louis’s fights in rapid succession, against Jack Kracken (July 4, 1934), Willies Davies (July 12, 1934), Art Sykes (October 24, 1934), Roy Lazer (April 12, 1935), and Harry Thomas (April 1, 1938). 54. Wilfred Smith, “Charles Wins; New Champion,” Tribune, June 23, 1949. 55. William Nack, “The Long Count,” Sports Illustrated 87, no. 12 (September 22, 1997): 74. 56. Paul Gallico, Farewell to Sport (New York: Simon and Schuster 1988, [1937]), 84. 57. “Called Racketeer, Cleared by Court,” New York Times, June 5, 1932. 58. In a similar vein, Miller was incensed when New York journalist Edward Dean Sullivan labeled him a “racketeer” in Rattling the Cup on Chicago Crime (New York: Vanguard), a 1929 exposé of Chicago crime. He sued for libel and won, receiving a token award of six cents. (See “Called Racketeer, Cleared by Court,” New York Times, June 5, 1932.) 59. “Confess Bribery to Free Hershie Miller of Murder Charge,” Daily News, October 26, 1921. The brothers referred to are likely Davey, Hirschie, Harry, and Max. Al, though apparently involved in some of the brothers’ criminal operations, had a lower profile than the others. Two additional brothers, Jack and Ben, seem to have had no criminal allegations against them. There were two sisters in the family as well, Sarah, who married Sam Edelstein, Davey Miller’s official

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partner in the M&E Restaurant, and Esther, who married Harry Block, owner of a Maxwell Street–area restaurant that was often labeled a gambling center itself. 60. Most of such voter intimidation went unrecorded, but Miller was indicted by a grand jury for attempted voter fraud in 1920 when, while he was serving as a judge of election in the 34th Ward, investigators found thirty-eight votes had already been recorded before the polling place even opened. See “38 Votes Cast Too Quick; Five to Face Grand Jury,” Tribune, April 17, 1920. 61. John Landesco, Organized Crime in Chicago (Chicago: University of Chicago Press, 1968 [1929]), 231. Note, the work was originally published as Part III of the Illinois Crime Survey. 62. “Detroit Rummer Admits Business of $5,000,000,” Tribune, May 3, 1927; and “Border Liquor Trade of $5,000,000 a Year Admitted by Savard in Canadian Inquiry,” New York Times, May 3, 1927. 63. “Hunt Three in Loop Rum Feud Shooting,” Chicago Evening American, January 21, 1924. 64. “Murder Bares Tilting of Lid on Gambling,” Tribune, March 16, 1924; and “400 Arrested in Raids on Crime, Vice, Moonshine,” Tribune, June 11, 1923. 65. “Sailor Friedman and Four Others Held as Slayers,” Tribune, April 11, 1922; and “Stray Shots Hit Abe Rubin, Jury Told By Witness,” Tribune, April 15, 1922. 66. “Sailor Friedman Freed of Murder,” Detroit Free Press, June 21, 1923. 67. CCC memo titled “In re: Case of Murder of Abe Rubin, 1900 West Division Street,” dated April 10, 1922. 68. “Commission Bars Sailor Friedman,” Houston Post, May 23, 1923; and “Sailor Friedman Freed of Murder,” Detroit Free Press, June 21, 1923. 69. Policeman Kills $3000 Bandit in Fire Escape Duel,” Tribune, January 25, 1919. 70. “57 Heroes Named for City’s D.S.C.; Only 2 Medals,” Tribune, January 21, 1920. 71. “Thieves Steal 13 Barrels of Whisky from Saloon,” Tribune, March 19, 1920; and “Harrison is Back of Manny Abrahams,” Day Book, February 15, 1913. In what would similarly strain credibility for being just a coincidence, another of Harry Miller’s high-profile arrests came when he caught two men who had robbed a patron at his brother-in-law Harry Block’s Maxwell Street restaurant (“Rob 12 Victims in Wild Run with Stolen Machine,” Tribune, July 21, 1919). 72. “Special Order of Chief Fires Cop Once ‘Hero,’” Tribune, December 28, 1921. 73. “Marked Bills Trap Police in ‘Dope’ Plot,” Tribune, July 1, 1925; and “Fires Two Cops Charged with Dope Grafting,” Tribune, August 5, 1925. 74. Max Allan Collins, True Detective (New York: St. Martin’s, 1983), 3. 75. Perhaps the two most prominent supporters of that conspiracy theory were Judge John Lyle, a noted Syndicate foe, and Frank Loesch, president of the Chicago Crime Commission. See Lyle, Dry Lawless Years, 266–68. Nitti biographer Ronald Humble argues that J. Edgar Hoover thought the theory credible as well (see Ronald Humble, Frank Nitti: The True Story of Chicago’s Notorious “Enforcer” [Fort Lee, NJ: Barricade Books, 2007], 179–92). For a more balanced assessment, one that emerges as generally skeptical of the conspiracy theory, see Mars Eghigian’s After Capone: The Life and World of Chicago Mob Boss Frank “The Enforcer” Nitti (Nashville, TN: Cumberland House, 2006), 249–51. 76. One of the few records of Hirschie Miller’s boxing career, “Earl Puryear Given Decision over Cepek,” Munster, Indiana Times, March 8, 1918, suggests he was lackluster as a professional fighter, describing him as “plodding” through a four-round victory. 77. “Turn Applicants Down,” Tribune, October 13, 1921. 78. See Chicago Crime Commission “Memorandum for Operating Director,” dated June 27, 1922, in file #2762 related to the trial of Max Miller, William “Sailor” Friedman, William Cohen, David Edelman, and Louis Romano. 79. “News of the Day Concerning Chicago,” Chicago Day Book, February 22, 1915; and “742 Locked Up as Police Mop Up Crime Dens,” Tribune, November 22, 1920, for his purchase of his brother-in-law Harry Block’s place. 80. Schoenberg, Mr. Capone, 59.

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81. A teenage Irle Waller happened to be there that night, listening to King Oliver on trumpet and watching the risqué dancing show. Forty-five years later, he recalled ducking out as soon as the shooting began (Irle Waller, Chicago Uncensored: Firsthand Stories about the Al Capone Era [New York: Exposition Press, 1965], 74). 82. “Slays 2 Police; City Hall Scandal Brews,” Chicago Daily News, August 23, 1920. 83. “Confesses to Killing 2 Policemen in Dive Fight,” Chicago Daily Journal, August 23, 1920. 84. “Pekin Slayer Gives Lead to Booze Graft,” Tribune, August 25, 1920. 85. “Slays 2 Police; City Hall Scandal Brews,” Chicago Daily News, August 23, 1920. 86. “See Big Liquor Scandal in Death of 2 Policemen in So. Side Cabaret Battle,” Chicago American, August 23, 1920. 87. “Slays 2 Police; City Hall Scandal Brews,” Chicago Daily News, August 23, 1920. 88. “Call Editors in Bribe Story,” Chicago Daily News, October 27, 1921; “Find Woman in Miller Case,” Chicago Daily News, October 28, 1921; “‘Missing’ Girl Witness Denies She was Bribed,” Tribune, October 29, 1921; “Confess Bribery to Free Hershie Miller of Murder Charge,” Daily News, October 26, 1921. 89. “Guard Hershie Miller to Foil Jail Break Plot,” Tribune, August 31, 1920. 90. “Hersche Miller, ‘Nails’ Morton, Escape Noose,” Tribune, October 2, 1921. 91. “Acquit Miller and Morton in Slaying of Cop,” Herald-Examiner, January 8, 1922. 92. Chicago Crime Commission memo headlined “In re: Labor Trials Investigations,” March 29, 1922. 93. “Mystery in Miller Attack,” Daily Journal, March 13, 1924; and “Jeweled Gang Held as Trying to Kill Hirchie,” Tribune, March 16, 1924). 94. “Woman Again Warns of Miller Bombing Plot,” Chicago Evening Post, March 14, 1924; and “Beer Lords’ Arrest Near in Outrages” Daily News, March 17, 1924. 95. “Guard Miller After Two Attempts to Kill Him,” Chicago Daily Journal, March 16, 1924. 96. Genevieve Forbes, “Hirchie Bad? Nope, A Saint, Says His Wife,” Tribune, March 16, 1924. 97. “Hirchie Miller Smiled on by Lady Luck,” Tribune, August 25, 1924. 98. “‘Putty’ Anixter Calls Dice Raids Gamblers’ War,” Tribune, December 22, 1919. 99. Bergreen, Capone, 361–63, 367; Schoenberg, Mr. Capone, 178–79. 100. See CCC memos from April 10, 1922, and May 8, 1922, in Rubin Killing file. 101. See Sullivan, Rattling the Cup, 13. Sullivan was referring to John Duffy, aka John Dougherty, a Philadelphia hood who, having come to Chicago, murdered his girlfriend in a bizarre episode that made the front pages and drew further attention to Hirschie Miller at the same time as he endured his racketeering difficulties. Davey Miller subsequently won a libel suit against Sullivan, but historian Rose Keefe suggests there was some truth to the account, at least up to the point where north-side boss Dean O’Banion realized that Duffy was entirely unsuitable for the task (Rose Keefe, Guns and Roses: The Untold Story of Dean O’Banion, Chicago’s Big Shot Before Al Capone [Nashville, TN: Cumberland House, 2003], 169). 102. CCC confidential memo titled “In re: Case of Murder of Abe Rubin, 1900 West Division Street,” dated April 10, 1922. 103. This was the incident that my mother came across in Art Cohn’s The Joker Is Wild. In the paperback edition she first shared with me, Cohn gets it backward, insisting that Davey had the bullet deflect off his belt buckle while Maxie was instantly killed. In a bit of publishing history I have never been able to untangle, however, the original hardcover version of the biography correctly reports that it was Davey who was ultimately shot. My mother’s original question, then, grew out of what seems an editing error. 104. For the best summary of Miller’s role in the May 29, 1923, boxing match between Benny Leonard and Pinkie Mitchell, see Jim Bowman, “How a Pioneer Fight Promoter Helped Knock Out Illinois’s Boxing Ban,” Tribune, May 6, 1984. 105. “Hunt Three in Loop Rum Feud Shooting,” Evening American, January 21, 1924.

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106. “Davy Miller Near Death; Brother Hit,” Tribune, January 21, 1924. 107. Murray, Legacy of Al Capone, 54. 108. “Hunt Three in Loop Rum Feud Shooting,” Evening American, January 21, 1924. 109. “Gang War Over Miller Feared,” Herald Examiner, January 21, 1924. 110. Keefe, Guns and Roses, 69–74. 111. William Shepherd, “How to Make a Gangster,” Collier’s 92, no. 10 (September 2, 1933):

112. For instance, Hirschie’s restaurant, then at 127 S. Kedzie on the northern edge of greater Lawndale, above Syndicate-owned places, was subject to nuisance raids on July 21, 1927, and October 20, 1928. See Tribune “Hirschie Miller Arrested in Dry Raid on New Café,” Tribune, July 22, 1927; “Legislator Hit by True Bill under Dry Law,” Tribune, October 20, 1928; and “Hirschie Miller Just Mystified by Café Raid,” Herald-Examiner, July 23, 1927. 113. Collis Jordan, “Death Comes to Bed of Hirschie Miller,” Chicago Daily Times, July 13, 1939. 114. Marovitz interview with the author, March 28, 1997, “I got a lot of strength from the fact that Davey was my friend,” Marovitz said. 115. See Ross and Abramson, No Man Stands Alone, 87, “All of us amateur fighters were crazy about Dave.” 116. See Warren Commission, 14:409–10, for Earl Ruby testimony about Ruby’s admiration for Miller and Ross as Jewish tough guys. 117. “Miller’s ‘Joints’ Shut Once More,” Chicago Daily News, June 2, 1928. 118. “Fights Friday, So Armstrong Goes to Work,” Tribune, February 19, 1938. 119. “Putty Anixter Funeral Today Will Be Private,” Tribune, December 21, 1943; in a family history commissioned by Anixter’s sons that made no mention of his alleged criminal involvement, Charles Bernstein and Stuart Cohen give a different account of the nickname’s origin. They claim that, when he was an infant, his older brother remarked, “What a putty (meaning pretty) baby,” Torah and Technology: The history and Genealogy of the Anixter Family (Chicago: Privately published, 1986), 226. 120. See also Bernstein and Cohen, Torah and Technology, 226. 121. “Chicago Gangs Turn from Beer to Crap Games,” Greenville, SC News, March 19, 1933). Another wire story from the same era spelled it simply as “Puddy.” C. C. Nicolet, “All Chicago Racketeers Have Very Itchy Fingers,” Pittsburgh Press, July 11, 1933. 122. “Chicago Poles Could Not Stage a Pogrom Yesterday,” Chicago Daily Courier, June 9, 1919, archived online as part of the Newberry Library’s Foreign Language Press Survey at http:// flps.newberry.org/article/5423972_2_0816. 123. “Buys Site for 36-Flat Building,” Tribune, December 13, 1913; and Inter Ocean real estate transactions, December 13, 1913; for Anixter’s age, see Bernstein and Cohen, Torah and Technology, 226. 124. “Conviction or Freedom Rests with Witness,” Tribune, December 21, 1917. 125. “News of the Day Concerning Chicago,” Day Book, February 7, 1917. 126. “Police Bribes Laid to Anixter,” Tribune, January 11, 1919. 127. See “More Cruelties of ‘Hard-Boiled’ Smith Revealed,” Tribune, July 21, 1919, for a note about Harry G. Green, same address as the letter writer, returning from overseas fighting. In his letter Green refers only to “sailing for France.” Although unpublished, Green’s letter appears in the Tribune’s online historical archive; I suspect it was part of the paper’s longtime files and was simply scanned as part of the larger digitization project. 128. See “‘Wise Men’ Double Money Selling Sites for Schools,” Tribune, January 11, 1914; “Widow Reveals ‘Manny’ Abrahams School Site Deals,” Tribune, February 6, 1914; “Goldman Recites Manny’s Story of School Site ‘Tips,’” Tribune, February 13, 1914; and “Trace Letter as Advance ‘Tip’ on School Site Deal,” Tribune, February 15, 1914. Anixter’s name does not appear in that press coverage.

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129. Green’s letter is contained in the Historical Chicago Tribune Index and is dated August 11, 1919. 130. “‘Biggest Fish’ Ducks; 75 Seized in Gaming Raids,” Herald and Examiner, December 21, 1919. 131. “‘Putty’ Anixter Calls Dice Raids Gamblers’ War,” Herald and Examiner, December 22, 1919. 132. “Chicago Gangs Turn from Beer to Crap Games,” Greenville, SC News, March 19, 1933. 133. Schoenberg, Mr. Capone, 186 and 194; see also Eghigian, After Capone, 225–26. 134. “Gamblers Scared,” Examiner, November 27, 1920. 135. “Murder Bares Tilting of Lid on Gambling,” Tribune, July 21, 1924. 136. “U.S. Jury Indicts Skidmore Again for Tax Evasion,” Tribune, March 1, 1940. 137. “Barrett’s Agents Force 1,000 Bookies to Close,” Decatur Herald, March 4, 1941. 138. A lengthy Tribune story, “Many Murders in Gilbert Era Still Unsolved,” from November 6, 1950, traces that wave of killings.

Notes to Chapter 5 1. Milton Rakove, We Don’t Want Nobody Nobody Sent (Bloomington: Indiana University Press, 1979), 61; and Charles Leroux and Ron Grossman, “Newcomers Enter the Mix of Neighborhoods, Politics,” Tribune, February 10, 1999. 2. Rakove, We Don’t Want Nobody Nobody Sent, 62. 3. Leroux and Grossman, “Newcomers Enter the Mix of Neighborhoods, Politics,” Tribune, February 10, 1999. 4. For an extensive consideration of the role of the ward committeeman, see Milton Rakove, Don’t Make No Waves, Don’t Back No Losers (Bloomington: Indiana University Press, 1975), 107–11. Rakove took the title of his study from an interview with Bernard Neistein, who claimed that those were his only two political rules, 11. 5. Rakove, We Don’t Want Nobody Nobody Sent, 69. 6. Granger and Granger, Lords of Last Machine, 106–7. 7. Rakove, We Don’t Want Nobody Nobody Sent, 62 and 70–71; see also Paddy Bauler (Granger and Granger, Lords of the Last Machine, 107). 8. See “Officials Swing Into Drive for Honest Voting,” Tribune, March 29, 1936; and “Vote to Indict 7 in Primary Election Plot,” Tribune, July 27, 1939, for two examples. 9. Rakove, We Don’t Want Nobody Nobody Sent, 59. 10. Ron Grossman, “Remembering Chicago’s Lawndale Neighborhood, and Other Places of Childhood,” Tribune, February 23, 2016. 11. Rakove, We Don’t Want Nobody Nobody Sent, 61. 12. Asbury, Gem of the Prairie, 277. 13. Wendt and Kogan, Lords of the Levee, 343–46. 14. Fred Pasley, Al Capone: The Biography of a Self-Made Man (Garden City, NY: Star Books, 1930), 43. 15. Rakove, We Don’t Want Nobody Nobody Sent, 67. 16. “Esskaye Chief Faces Cell as Aids Hesitate,” Tribune, May 4, 1932; and “Kleagle Clarke Is Locked up in Psychopathic,” Tribune, June 22, 1932, for Klan story; “L. J. Grossman Dies; 5th Ward Ex-Alderman,” Tribune, June 12, 1956, for Jewish involvement. 17. Arthur Evans, “Igoe to Support Eaton Against Grossman in 5th,” Tribune, February 15, 1929. 18. “Experts Still Drawing Plums from City Funds,” Tribune, August 4, 1929; and “$38,100 Salary Tops City List of 1930 Experts,” Tribune, March 8, 1931. 19. “Grossman Charges Called ‘Politics,’” Chicago Examiner, October 20, 1932. 20. Chicago Crime Commission memo dated October 18, 1932.

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21. “Grossman Charges Called ‘Politics,’” Chicago Examiner, October 20, 1932. 22. CCC file 65–73, dated February 18, 1944, 2. 23. Virgil W. Peterson, “The Vicious System of Protected Privilege,” Criminal Justice 71 (April 1944): 3. 24. “The Score on Chicago Gambling,” Tribune, February 25, 1944; I should note that the Tribune was reacting to a spoken version of the talk that Peterson would publish later in Criminal Justice. The Tribune carried a summary of that talk on February 18, 1944. 25. “Judges and Clerks of Election,” Chicago Evening Post, March 7, 1924. 26. “Gun Toter Freed By Police Star of Sanitary Board,” Tribune, July 10, 1928. 27. “Courtney Axes Demolish Third Gambling Dive,” Tribune, August 20, 1938. 28. “Partner Dies Hearing News,” Chicago Sun, January 15, 1944; I believe, from other contemporary documents, that the address is a typo and should read 3216 Roosevelt Rd. 29. “Courtney Axes Demolish Third Gambling Dive,” Tribune, August 20, 1938. The Examiner did report it contemporaneously, but they thought it worth only a two-inch notice under a small headline (“Grossman Charges Called ‘Politics,’ ” Chicago Examiner, October 20, 1932). 30. See “Nab Suspects in Shooting of Grid Star,” Tribune, November 14, 1928. The news story gives no details, just a passing mention that Zuckerman had been arrested for beating up a waiter. The charges were presumably dropped. 31. “Auto Gang Gets Bank’s $3500 in Street Holdup,” Tribune, August 3, 1921. 32. The four were Frank “Lefty” Koncil and Charles Hrubek of the north-side–allied Joe Saltis gang, Alphone Fiori of the mostly depleted Genna gang, and Benjamin “Schoolmaster” Schneider, a longtime near-west-side figure (“Fourth Killing Gives Police New Gang Mystery,” Tribune, March 14, 1927). Researcher Wayne Johnson points out that newspapers actually missed a fifth Chicago gang killing from the same few days (Johnson, A History of Violence: An Encyclopedia of 1400 Chicago Mob Murders [McLean, VA: LLR Books, 2014], 94), Tomasso Piazza, whose murder wasn’t reported until the end of the month. 33. “‘Alky’ Dealer Shot Down as He Enters Home,” Tribune, March 16, 1927. 34. “Guns Roar Again in Chicago Gang War,” Joplin, Missouri Globe, March 17, 1927. 35. Ibid. 36. Details of Acher’s shooting come from “‘Doc’ Acher in Serious Condition,” Daily Northwestern, November 13, 1928; “Struck in Spine, Full Back May Be Life Cripple,” Tribune, November 12, 1928; “Auto is Clew in Shooting of Football Player,” Tribune, November 13, 1928; “Nab Suspects in Shooting of Grid Star,” Tribune, November 14, 1928; “Decide to Leave Gang Bullet in Fullback’s Spine,” Tribune, November 15, 1928; and wire stories “Celebrator Shot By Chicago Gunmen,” Sedalia, MO Democrat, November 12, 1928; and “Gangsters Shoot Football Player After Accident,” Davenport, IA Daily Times, November 12, 1928. 37. “Hold Acher Funeral,” Davenport, IA Daily Times, May 17, 1929. 38. “Football Celebrant is Shot By Gangster,” Chillicothe, OH Gazette, November 12, 1928. 39. “‘Doc’ Acher in Serious Condition,” Daily Northwestern, November 13, 1928. 40. “Nab Suspects in Shooting of Grid Star,” Tribune, November 14, 1928. 41. See John Sayle Watterson, College Football: History, Spectacle, Controversy (Baltimore, MD: Johns Hopkins University Press, 2002), 51–53 and 150–52, for the general nature of betting college football in the era. See also Gerald R. Gems, Pride, Profit and Patriarchy (Lanham, MD: Scarecrow Press, 2000), 138, for the claim that the Big 10 conference, which included Northwestern, was particularly known for the problem. 42. Paul Myerberg, “Al Capone Went to Northwestern-Nebraska Before Going to Prison,” USA Today, October 19, 2012; see also “Daily’s Stand on ‘Al’ Capone Incites Notice,” Daily Northwestern, October 13, 1931, where the student author not only notes that Capone attended at least two games that season but also writes, “The campus has not forgotten how John ‘Doc’ Acher was killed by a gunman after the Purdue game several years ago.” 43. See Roger Biles, Crusading Liberal: Paul H. Douglas of Illinois (DeKalb, IL: Northern Illinois University Press, 2002), 30–32.

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44. See Eghigian, After Capone, 225–26, for his discussion of how Frank Nitti won Bill Johnson and Billy Skidmore, longtime associates and protégés of Anixter, into the Syndicate fold. 45. “Courtney Axes Demolish Third Gambling Dive,” Tribune, August 20, 1938. 46. “Lid is Clamped on Lake County Slot Machines,” Tribune, August 23, 1939. 47. “A Mystery Cop Gets Spotlight in Gaming Quiz,” Tribune, October 15, 1943. 48. “Expose More Gang Secrets,” Tribune, October 26, 1941; the Tribune obtained this information from ledgers that Syndicate boss Jack Guzik inadvertently left in an apartment he briefly rented. 49. “Lay Zuckerman Killing to Gang Greed for ‘Cut,’” Tribune, January 18, 1944.

Notes to Chapter 6 1. H. L. Meites, History of the Jews of Chicago: Facsimile of the Original 1924 Edition (Chicago: Chicago Jewish Historical Society and Wellington Publishing, 1990 [1924]), 319. 2. Ibid., 425, 427. 3. “Twentieth Ward—Vote for Heller,” Tribune, March 30, 1913. 4. Ira Berkow, Maxwell Street: Survival in a Bazaar (New York, Doubleday, 1977), 5–6. 5. Ibid., 246. 6. Cutler, Jews of Chicago, 60; see also Bernard Horwich, My First Eighty Years (Chicago: Argus Books, 1939), 121–29, for a memoir of the hardships associated with peddling at the turn of the twentieth century. 7. James O’Kane theorizes this experience in The Crooked Ladder when he notes that there are seven “core routes of mobility from the lower classes to the middle classes” (28). He characterizes five of them—unskilled and semiskilled labor, retail small business, the professions, the clergy, and entertainment—as conforming with the law. He sees another—organized crime—as clearly illegitimate. In the final instance, however, he notes that “urban politics” is “a semilegitimate mode of upward mobility since the established society is ambivalent towards ethnic politicians” (28). Abrahams embodied that contradiction, as Jacob Arvey would over the course of the following generation. He was someone who clearly took much of his authority from his links to organized crime, yet he himself remained in a legal position as a law-making, legislative figure. 8. Wendt and Kogan, Lords of the Levee, 75–77. 9. For Powers, see Lindberg, Gangland Chicago, 195. For Cermak, see Gottfried, Boss Cermak, 16. To be clear, Cermak doesn’t seem to have owned his own saloon, but he took a leadership role in the community that formed around it. 10. John Landesco’s Illinois Crime Survey, written in 1929 with a chapter on Chicago’s illegal gambling over the previous twenty-five years, identifies Abrahams in 1911 as a “west side saloonkeeper, ruler of Nineteenth Ward gambling,” 63). The city would pass a substantial remapping of its ward boundaries in 1921, effective in 1923, that created fifty wards with one alderman apiece where there had been thirty-five with two aldermen in each. See “Fifty Ward Plan Passes Council; Vote is 53 to 3,” Tribune, July 23, 1921. 11. “‘Wise Men’ Double Money Selling Sites for Schools,” Tribune, January 11, 1914. 12. See Inter Ocean, October 8, 1897, for notice of Chicago Tammany inception. See also Madelon Powers, “Decay from Within: The Inevitable Doom of the American Saloon,” in Drinking: Behavior and Belief in Modern History, ed. Susanna Barrows and Robin Room (Oakland: University of California Press), 123, for a discussion of the role of saloons in the Tammany system. 13. “Specimen Ballot—1st Congressional District, 3d Senatorial District,” Inter Ocean, November 5, 1898. 14. “Police Station Is Robbed,” Inter Ocean, October 17, 1902. 15. “Games Backed by Police,” Tribune, July 29, 1906. 16.“The State Capital: All Fixed on Charter Plan,” Carbondale, IL Daily Free Press, April 26, 1907.

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17. “Lorimer’s Fight to Save Toga Told in Munsey’s,” Washington Times [reprinting Munsey’s editorial], May 1, 1911. 18. “The Lorimer Tragedy,” Orangeburg, SC [reprinting NY World editorial], April 15, 1911. 19. “Senator Crawford Aids Beveridge in Fight on Lorimer,” Wilkes-Barre, PA Times-Leader, January 10, 1911. 20. “Tears for Lorimer,” Washington Post, February 23, 1911; “Lorimer Explains Senate Election,” Scranton Republican, January 13, 1912. 21. “New Gossip Chapter Put in Lorimer Tale,” Inter Ocean, November 11, 1911. 22. “‘Manny’ Abrahams’ Saloon Blown,” Decatur, IL Daily Review, August 1, 1912; and “Fifty Families Periled by Bomb in Political War,” Inter Ocean, February 18, 1913. 23. In an incident that shows the just-beginning movement of Jewish gangsters to Lawndale, Deputy Police Superintendent Herman Schuettler, a notoriously incorruptible figure, retaliated with a raid on Jewish-run gambling in Lawndale at Roosevelt and Kedzie, where Davey Miller would open his place within a couple years (“Schuettler Raid Angers Abrahams,” Tribune, June 9, 1913). 24. “Hearst-Harrison Forces Defeated at City Primary,” Tribune, February 26, 1913. 25. “Lie Is Passed by Czarnecki in Fick Hearing,” Inter Ocean, March 18, 1913. 26. “Voters’ League Aldermanic Candidates Win; Hearst-Harrison Faction Loses City Ticket,” Inter Ocean, March 26, 1913. 27. “Abrahams Accused in Graft Charges,” Inter Ocean, June 5, 1913. 28. “Widow Reveals ‘Manny’ Abrahams School Site Deals,” Tribune, February 6, 1914; Julius Anixter was linked to the same scheme. 29. “Ald. Abrahams Dies; Stricken in Meeting,” Inter Ocean, July 2, 1913. 30. “Mrs. Abrahams for Manny’s Seat,” Tribune, January 13, 1914; and “Mrs. Abrahams Wants Job Her Husband Had,” Day Book, January 13, 1914. 31. “Winners in Aldermanic Primaries,” Tribune, February 25, 1914. 32. “Probe Tale That Beer Lords Buy Jail Privileges,” Tribune, June 6, 1925. 33. Kobler, Capone, 141–42; “Jailer Signs Statement on Druggan Bribe,” Tribune, September 23, 1925; “Westbrook Home Again; Shows Strain,” Tribune, September 24, 1925; “Cites Case of Sheriff Given 90 Day Term,” Tribune, September 30, 1925; and “One Month for Hoffman, Four for Westbrook,” Tribune, October 15, 1925. 34. Kenneth Allsop, The Bootleggers, (New Rochelle, NY: Arlington House, 1968), 109–10. 35. “Chicago Stops Violence at Polls,” New York Times, November 3, 1926; and “Little Disorder Marks Election; Not a Gun Fired,” Tribune, November 3, 1926. 36. “Vote for Morris Eller,” advertisement, Tribune, September 10, 1918. 37. “Seen and Heard,” Jewish Daily Courier, March 17, 1907, archived online as part of the Newberry Library’s Foreign Language Press Survey at http://flps.newberry.org/ article/5423972_4_1_0316/. 38. “Charges He Paid Tribute for Job,” Tribune, February 28, 1916. 39. Asbury, Gem of the Prairie, 241–8 and 309–11; Douglas Bukowski, Big Bill Thompson, Chicago, and the Politics of Image (Urbana: University of Illinois Press, 1998), 22–30; and John R. Schmidt, The Mayor Who Cleaned Up Chicago (DeKalb: Northern Illinois University Press), 51–56. 40. “Vote for Morris Eller,” advertisement, Tribune, September 10, 1918. 41. “5 More Desert Mayor’s Leaky Ship of State,” Tribune, December 9, 1921. 42. “300 Accused of Election Fraud, Clinnin States,” Tribune, June 9, 1921. 43. “Emanuel Eller, Republican,” Tribune, November 3, 1923; Eller fired back at the Bar Association, accusing them of anti-Semitism in their refusal to endorse two additional Jewish candidates and in their persisting in their criticism of Emanuel (“Eller Sees Race Hatred in Fight to Unseat Son,” Tribune, December 23, 1923). 44. “Eller Rolls Up Whale of Vote in His Home Ward,” Tribune, November 9, 1923.

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45. Carroll H. Wooddy, The Case of Frank L. Smith: A Study in Representative Government (Chicago: University of Chicago Press, 1931), 67 46. “Indicted Boss Balks on His Pledge to Jury,” New York Times, August 6, 1926; and “A Chicago ‘Leader,’” New York Times, August 7, 1926. 47. “Aids of Eller Seized After Mystery Blast,” Tribune, October 25, 1931. 48. In addition to being widely reported as a member of the Portugese gang, Kaplan put himself forward as Portugese’s best friend, most prominently taking a hand in the funeral the Herald and Examiner mistakenly took to be “traditional.” The report called Kaplan “master of ceremonies” once the ceremony moved outside to Jewish Waldheim Cemetery (“Hold Service for Portugese,” Chicago Herald-Examiner, July 17, 1926). 49. “Hunt Twelve Jury Indicted as Terrorists,” Tribune, July 1, 1928. 50. “Twelve Taken in $150,000 Whisky Raid,” Chicago Daily News, August 24, 1920. 51. As far as I can tell, that particular term originated in a report produced by what became known as the Wickersham Commission, a committee convened by Herbert Hoover to investigate Prohibition criminals nationwide and headed by former US Attorney General George Wickersham (see National Commission on Law Observance and Enforcement: Report on the Causes of Crime, vol. 4 [Washington: U.S. Government Printing Office, 1931], 304). 52. “Aids of Eller Seized After Mystery Blast,” Tribune, October 25, 1931; and “Probe Blast in Which Eller’s Kinsman Is Hurt,” Tribune, October 26, 1931. 53. “Holds Dry Raiders in Chicago Shooting,” New York Times, August 25, 1928, shows the extent of Paul Morton’s bootlegging operations, inherited apparently from his brother Samuel “Nails” Morton. Morton’s 20th Ward ties are clear from his early link to Hirschie Miller in the August 26, 1920, shooting at the Pekin Inn. 54. Kaufman was less directly a 20th Ward figure, though his nickname, “Potatoes,” did purportedly come from his family’s involvement in the potato market (Rose Keefe, The Man Who Got Away: The Bugs Moran Story, A Biography [Nashville, TN: Cumberland House, 2005], 112) which would have gone through the markets Eller controlled. 55. Foster and Eller are linked chiefly through the revelations in the papers Jack Zuta left behind after his assassination. See “Zuta Records Spur Denials in Chicago,” Tribune, August 17, 1930. 56. “Capone’s Decade of Death,” Tribune, February 16, 1936. 57. “Thuggery Told at Trial of 16 Ward Henchmen,” Tribune, October 16, 1928. 58. “Morris Eller Supplied Guns to ‘Bloody 20th’ Ward Gangsters; Promised Protection, Witnesses Tell Jury,” Tribune, October 31, 1928; a second witness claimed the guns would be available at a different house, not Manny’s, but he confirmed the idea that Eller was arming his election squad the night before. 59. Manny had some precedent for such a practice, having held court in his own home to free campaign workers in the 1926 primary. “Chicago Stops Violence at Polls,” New York Times, November 3, 1926. 60. “Tells of Terror as Eller Calls Ward Peaceful,” Tribune, May 3, 1928. 61. “Cleanup of Gangsters Is under Way,” Tribune, April 12, 1928. 62. “Granady Inquest Halted,” Defender, April 21, 1928. 63. “Cleanup of Gangsters Is under Way,” Tribune, April 12, 1928; the Defender cited testimony that the lead car in the squadron of three was the one in which Eller himself was riding (“Granady Inquest Halted,” Defender, April 21, 1928).

Notes to Chapter 7 1. Some evidence for that comes from the widespread sense at the time that Thompson’s election would lead to legalizing prizefighting in Illinois (“Local Fans See Boost for Fight,” Tribune, April 9, 1915). While amateur fighting was legal, professional boxing remained illegal until 1926. For an interesting footnote, see coverage of the Benny Leonard–Pinky Mitchell fight, refereed by

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Davey Miller on May 29, 1923 (see “How a Pioneer Fight Promoter Helped Knock Out Illinois’ Boxing Ban,” Tribune, May 6, 1984, for a looking-back summary) 2. “Twelve Taken in $150,000 Whisky Raid,” Chicago Daily News, August 24, 1920. 3. “‘Action’ Certain at Dave Miller’s,” Tribune, May 28, 1928; I present this as “legend” because, while Miller seems to have purchased the pool hall in early 1915, it’s unlikely he embraced all the opportunities quite so quickly. The Tribune reports that the Thompson administration revoked his license on September 24, 1915 (“Mayor Revokes Bar Licenses”). According to the Day Book, “News of the Day Concerning Chicago,” September 29, 1915, he had it restored almost immediately. Reading between the lines suggests he reached an accommodation with the new administration. The Tribune’s 1928 story then may not be true in its exact date, but it reflects the larger truth that Miller’s rise was linked to Thompson’s election. 4. Martin Luther King, Jr., once referred to Douglas as “the greatest of all Senators” (James L. Merriner, “Illinois’ Liberal Giant, Paul Doulas,” Tribune, March 9, 2003). For Arvey’s role in selecting Douglas as senate candidate, see Biles, Crusading Liberal, 43–45. 5. Porter McKeever, Adlai Stevenson: His Life and Legacy (New York: William Morrow, 1989), 107–14; and Sean Savage, Truman and the Democratic Party (Lexington: University of Kentucky Press, 1997), 35. 6. Savage, Truman, 44–46. 7. “Jacob Arvey,” Tribune, August 27, 1977. 8. Berkow, Maxwell Street, 251. 9. Russo, Supermob, 18. 10. Berkow, Maxwell Street, 246–47. 11. Untitled note from Chicago Reform Advocate newspaper, February 17, 1923, archived online at Newberry Library’s Foreign Language Press Survey at http://flps.newberry.org/ article/5423972_4_1_0223/. 12. “Jacob Arvey,” Tribune, August 27, 1977. 13. Demaris, Captive City, 105. 14. “Democratic Leaders Pass in Same Hour,” Tribune, June 1, 1928; during the first election under those new lines, the Tribune’s immediate post-election analysis already referred to the 24th Ward as “Sanitary Trustee Michael Rosenberg’s democratic territory” (“Dever Sweeps in by 103,748,” Tribune, April 4, 1923). For background on the redrawing of the full city’s electoral map by wards, see “Fifty Ward Plan Passes Council; Vote is 53 to 3,” Tribune, July 23, 1921. 15. “Political Chief Dies Suddenly as Trial Nears,” Tribune, January 13, 1934. 16. Demaris, Captive City, 105. 17. “Moe Rosenberg’s Estate $15,000, Court is Told,” Tribune, February 1, 1934. 18. “Thousands Pay Last Tribue to Moe Rosenberg,” Tribune, January 16, 1934. 19. “Simpson Tells of $1,215,000 Sales to Moe,” Tribune, March 14, 1934. 20. “Police, After Bomb, Guard Ward Workers,” Tribune, November 10, 1926. 21. “Bury Rosenberg, Rites Tomorrow For Lindheimer,” Tribune, June 2, 1928. 22. “Eller Accused in Indictment of 23 Counts,” Tribune, August 4, 1928; and “Eller Henchmen Trial Tomorrow 576 Witnesses,” Tribune, September 19, 1928. 23. “‘I’m Boss,’ Eller Tells Jury,” Tribune, August 1, 1928; Dewey L. Fleming, “Election Day Gunman Slain in Chicago Bar,” Baltimore Sun, August 1, 1928. 24. “Police Guard Witness in Eller Trial from Gangster,” Tribune, October 23, 1928. 25. S. J. Duncan-Clark, “Smith Visit Gives Chicago Big Thrill,” New York Times, October 21, 1928. 26. “Eller Men Guilty; Escape with Fines,” New York Times, November 24, 1928; “Raber Will Start Move to Reindict Eller Followers,” Tribune, December 13, 1928; “Move to Balk Protection for Eller Witnesses,” Tribune, December 14, 1928; and “Jury Frees All in 2D Trial for Vote Terrorism,” Tribune, April 20, 1929. 27. Schoenberg, Mr. Capone, 172; Bergreen, Capone, 220–21.

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28. James Doherty, “The Vote Crop in 24th Ward Has High Yield,” Tribune, February 17, 1946. 29. “Here’s How Eller Takes Care of His Precinct Captains,” Tribune, May 4, 1928; Park Browne, “Wolff Turns on Eller; Fires Two of His Henchmen,” Tribune, August 16, 1928; and “Barrett Hews ‘Deadwood’ Out of State Office,” Tribune, January 20, 1941. 30. As it turned out, Arvey’s original successor as 24th Ward alderman was Fred Fischman, who won a special election to fill the remainder of Arvey’s term. Elrod immediately assumed the more powerful ward committeeman position, however (“39 Enter Race for West Side Council Seats,” Tribune, January 24, 1943). Elrod eventually held both positions. 31. “Found Bearded and Ill After 12 Days’ Terror,” Tribune, July 13, 1933. 32. “Police Decipher Phone Code of ‘Ted’ Newberry,” Tribune, January 13, 1933. 33. Joseph Ator, “Laundry Owner Tells of Threat and Bomb Sequel,” Tribune, February 25, 1934. 34. Orville Dwyer, “Disclose Ragen Told Sheriff of Gang-Run Books,” Tribune, July 6, 1946; James Ragen echoed this claim in the statement he gave to First State’s Assistant Attorney Wilbert Crowley on May 2, 1946, claiming that Syndicate political flunky Dan Serittella told him, “Arvey can’t do you any good, because our organization killed Zukey [sic] and Danny so-and-so [Louis Dann] is a fugitive from Chicago and Arvey is sucking our ass to get us to let Danny come back and not kill him,” 42 (copy of statement on file at CCC). 35. “2 Gangster Aids Step Into Case from Politics,” Tribune, September 27, 1947; and “National Crime and National Politics,” Tribune, October 1, 1947. 36. The Chicago Crime Commission documented Elrod’s links to Zuta very carefully, reporting on the fact in memos dated August 24, 1950, and December 20, 1950, and uncovering a probate record dated May 9, 1931, in which Elrod inherited a pair of Zuta’s properties worth $20,000 after he’d been killed (see CCC memo dated December 20, 1950, for evaluation). Otherwise, the link seems rarely to have made it into press coverage of Elrod’s highly visible political career. 37. For one humorous example of the Jewish Ettelson’s links to Capone, see muckraker Fred Pasley’s column, “Our Town: Anent the Passing Throng,” in the Tribune, November 4, 1928, in which he imagines a football lineup of Syndicate figures. He has Capone at right guard, Thompson at center, and Morris and Emanuel Eller alternating at fullback. Of Ettelson, whom he places at right halfback, he says, “And Sam Ettelson is famous for his versatility. He will double as cheerleader and in singing ‘Hail, hail, the gang’s all here.’” 38. See “City Employe Questioned on Slot Machines,” Tribune, March 13, 1929; and “Slot Machine Connection Costs Him Job with City,” Tribune, March 14, 1929. 39. CCC memo dated November 16, 1950. 40. “Court Dismisses Charges against Emanuel Eller,” Tribune, September 22, 1929. 41. Carl Wiegman, “Secret Police Methods Told at Ragen Quiz,” Tribune, August 26, 1947. 42. Drew Pearson, “Artie Elrod: Big City Boss,” Syracuse, NY Standard, July 22, 1952. 43. Drew Pearson, “Chicago Commission Gets Rich in Public Office,” Eau Claire, WI Leader, January 21, 1951. 44. James Doherty, “Believe Guzik May Be Key to Gambling War,” Tribune, April 9, 1945. 45. Crime Commission memo, April 20, 1948, file 65-73-55. 46. Demaris, Captive City, 125, and CCC memos April 9, 1945, and May 11, 1945. 47. “Arthur Elrod, County Board Member, Dies,” Tribune, July 23, 1959. 48. Patrick FBI file, dated June 17, 1958, prepared by Vincent Inserra, 21.

Notes to Chapter 8 1. Patrick testimony in Alex trial, 920–22. 2. “Pal of Caplis Slayers Shot; Names Old Foe,” Tribune, April 5, 1932. 3. Patrick testimony in Alex trial, 1160–1163.

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4. Patrick’s FBI file, report dated April 18, 1958, p. 4. 5. “Hunt Twelve Jury Indicted as Terrorists,” Tribune, July 1, 1928. 6. “Policeman’s Shot Solves Murder of Watchman,” Tribune, February 15, 1928; “Denies Holdup, Blames Cop in Killing of Two,” Tribune, February 16, 1928; and “Inquiry Ordered into Killing of 2 By Policeman,” Tribune, February 17, 1928). See 1910 census report on Morris Patrick for confirmation that Charles was, indeed, Lenny’s brother. 7. “Shoots His Son: Morris Patrick,” Tribune, September 8, 1932; in this news report, the older brother is identified as John rather than Jack. The names and dates of birth line up for Morris and Lenny Patrick, however, as does the detail that Morris Patrick worked for the court bailiff (See Patrick FBI file, report dated April 18, 1958, p. 4. See also “Son, Wounded by Father, Held on Robbery Charge,” Tribune, September 12, 1932, for armed robbery attempt. 8. For the detail that the shooting took place near a synagogue, see Patrick’s testimony in the Gus Alex trial, 1160. For its identification I have taken the address given for the Glick shooting in the newspapers—1319 S. South Sawyer—and crossed it with Kraus and Schwartz’s Walk to Shul, which locates Shaarei Torah Anshe Mauriv, nicknamed the Sawyer Avenue Shul and the oldest major congregation in Lawndale, at 1301 S. Sawyer. 9. Patrick testimony in Alex trial, 1162. 10. “39 Hoodlums on New ‘Public Enemy’ Roster,” Tribune, January 10, 1933. 11. “Victims Identify M’Geoghegan as Bank Robber,” Tribune, April 30, 1932. 12. “Chicago Killer Is Captive in Culver Holdup,” Tribune, May 31, 1933. 13. Patrick FBI file, report dated April 18, 1958, p. 7. 14. Ibid., report dated January 9, 1958, p. 4. 15. I make the claim that Patrick grew up in Lawndale from the FBI’s eventual determination that he attended Sheppard Grammar School near Francisco and Fillmore. The FBI could find no record of his attendance, but one informant recalled being a fellow student (report dated February 26, 1958, p. 5), and the FBI was able to locate records that Patrick’s brother Mike (also known as Meyer) was a student there (report dated April 18, 1958, p. 2). 16. Patrick FBI file, report dated April 18, 1958, p. 3. 17. Ibid., report dated February 6, 1958, p. 16. 18. Chicago Crime Commission memorandum, dated May 12, 1944, signed by E. C. Dixon, filed in 65–73–23 with original filed in 65–70. 19. Frank Cipriani, “Gambler Killed; Pal Dies,” Tribune, January 15, 1944. 20. James Doherty, “Find Syndicate Head Office in Loop Building,” Tribune, December 11, 1941. 21. “Levin, Capone’s Loop Boss, Dies,” Tribune, June 20, 1951. 22. Alex testimony, 925. 23. Ibid., 927. 24. Ibid., 926–27. 25. Demaris, Captive City, 125, and CCC memos April 9, 1945, and May 11, 1945. 26. Patrick told FBI interviewers in 1978 (Report of the House Select Committee on Assassinations, 9:963) that he met Yaras sometime in 1944. For Yaras as Guzik’s onetime chauffeur, see “Body of West Side Gambler Hung on Fence,” Tribune, March 22, 1950. 27. Alex testimony, 929. Note that testimony refers to Tarsch as “Kalatsch.” Newspaper coverage from Tarsch’s 1945 murder refers to him sometimes as “Galatz,” indicating this is the same man, but Tarsch is more common in the contemporaneous reports, and I have opted to go with that in the text. 28. Alex testimony, 941. 29. Ibid., 942. 30. Johnson, History of Violence, 201–2. 31. Chuck Goudie, “50 Years Later, Alderman Murder Still Open Case,” ABC 7, “Eyewitness News,” January 24, 2013, accessed September 21, 2017, archived at https://abc7chicago.com/ archive/8965861/.

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32. Patrick FBI file, teletype memo to director from Chicago, dated July 10, 1967. 33. Burton Turkus and Sid Feder, Murder, Inc.: The Story of the Syndicate (New York: Farrar, Straus and Young, 1951), 8. 34. For what it’s worth, longtime FBI agent William Roemer regarded Alderisio and Nicoletti as “the two deadliest shooters in the history of the Chicago Outfit,” Enforcer, 41. Other notorious Outfit hit men included Harry Aleman, Frankie “the German” Schweihs, and Tony Spilotro. 35. Roemer, Man against the Mob, 277. 36. Patrick FBI file, report dated June 17, 1958, p. 17. 37. Ibid., report dated January 9, 1958, p. 6. 38. Ibid., report dated November 13, 1972, p. 3. 39. Ibid., report dated January 9, 1958, p. 8. 40. Turkus and Feder, Murder, Inc., 24. 41. For a sense of the potential profits, consider that Annenberg was earning between $400,000 and $1.5 million a year, all of it profit and all of it legal (see Christopher Ogden’s Legacy: A Biography of Moses and Walter Annenberg [Darby, PA: Diane Publishing, 1999]) for $400k figure [98]; for $1.5 million [110]). Ragen himself admitted to earning in excess of $100,000 a year in 1946 (see Ragen statement to First Assistant State’s Attorney Wilbert F. Crowley and three members of the Chicago Police Department, May 2, 1946, p. 25, copy available in the files of the Chicago Crime Commission) 42. See Smith, Syndicate City, 34–35 and 168–69; also Charles Rappleye and Ed Becker, AllAmerican Mafioso: The Johnny Roselli Story (New York: Doubleday, 1991), 100–101. 43. See “Victim’s Own Story of Capone Gaming Control Board,” Tribune, June 26, 1946, for Levin; see William Braden, “He’s 75 and ‘Anonymous’—And Labeled as Mob Boss,” Tribune, December 22, 1991, for Alex. 44. Clayton Kirkpatrick, “Ragen Killers Botched It, But Still Go Free,” Tribune, October 11, 1950. 45. “Shooting Laid to Gangsters,” Wilkes-Barre, PA Evening News, June 25, 1946. 46. William J. Drury and Don Petit, “Ragen Slain By Mobsters,” Miami Daily News, March 9, 1950. 47. Ibid.; see also Clayton Kirkpatrick, “Poison! Word Puts New Life in Ragen Case,” Tribune, October 12, 1950. 48. Sam Giancana and Chuck Giancana, Double Cross: The Explosive Inside Story of the Mobster Who Controlled America (New York: Warner Books, 1992), 141. 49. James Doherty, “Indicted Cops to Bare Secrets of Ragen Probe,” Tribune, April 6, 1947. 50. Carl Wiegman, “No Threat to Police, Crowley Says,” Tribune, September 4, 1947. 51. “Witness Now Denies He Saw Ragen Suspect,” Tribune, March 29, 1947; note this article refers to him as James White, but subsequent ones refer to him as John. 52. James Doherty, “Race News Foes of Ragen Quit; Lose a Million,” Tribune, June 16, 1947; this article also notes the suspicious coincidence that the Syndicate backed Trans-America Company, a news service founded a year earlier in a failed bid to compete with Ragen’s Continental News Service, announced it was folding up shop. 53. George Wright, “Police Station File on Ragen ‘Witness’ Gone,” Tribune, October 11, 1947. 54. “Seeds of Drury Tragedy Found in Ragen Case,” Tribune, September 27, 1950. 55. Carl Wiegman, “Democrats Air Dirty Linen in Ragen Inquiry,” Tribune, August 22, 1947 and “Secret Police Methods Told at Ragen Quiz,” Tribune, August 26, 1947. 56. “Ambush Syndicate Foe; 2 Gunmen Kill Lawyer,” Tribune, September 26, 1950. 57. See Miami Daily News from March 2, 1950, to March 13, 1950, for Drury’s complete series. 58. “Ambush Syndicate Fore; 2 Gunmen Kill Lawyer,” Tribune, September 26, 1950. 59. Ibid. and “Ex-Chicago Cop Slain on Eve of U.S. Crime Quiz,” Long Beach, CA Independent, September 26, 1950. 60. “Why Drury Was Killed,” Tribune, September 28, 1950.

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61. Patrick FBI file, reports dated September 3, 1959, p. 4; and July 8, 1971, p. 42. 62. Johnson, History of Violence, 199. 63. “Obituary: Thomas E. Connelly,” Tribune, March 23, 1978. 64. Longtime FBI agent Bill Roemer tells the story that Patrick once came to him in tears. According to Roemer, the Chicago field office and the mob had a series of unwritten rules that included a hands-off policy for families. A young agent, unfamiliar with the protocol, tried to squeeze Patrick for information. To do so, he went to the family of Patrick’s daughter’s fiancé—“a society guy, a first-class legit family,” Patrick said—and told them their son was about to marry into the family of the man who’d murdered James Ragen. Roemer apologized, but there was no way to repair the engagement (Man against the Mob, 57–58)

Notes to Chapter 9 1. See Eghigian, After Capone, 216. 2. “Gunman is Shot Down By Police,” Sheboygan, WI Press, December 19, 1932. 3. Eghigian, After Capone, 219–20. 4. Ibid., 221–26. 5. When Newberry was murdered, police found Arvey’s telephone number in Newberry’s personal phone book (“Police Decipher Phone Code of ‘Ted’ Newberry,” Tribune, January 13, 1933). 6. See Lyle, Dry, Lawless Years, 254–68. For the Connelly-Drury comment, see Egighian, After Capone, 249–51. See also Lombardo, Organized Crime, 97–98. 7. Roger, Crusading Liberal, 44. 8. See Dick Simpson, Rogues, Rebels, and Rubber Stamps: The Politics of the Chicago City Council from 1863 to the Present (Boulder, CO: Westview Press, 2011), 99–100. 9. See Lombardo, Organized Crime, 98–99, for an analysis of the way payoffs shifted in the course of the Kelly administration. 10. Russo, Outfit, 2. See also James Doherty, “Accardo Called Capone Gang’s Chicago Boss,” Tribune, October 1, 1950. 11. See Robert Schultz, Soured on the System: Disaffected Men in Twentieth-Century American Film (Jefferson, NC: McFarland, 2012), 37–43, for a discussion of the film as a vehicle for negotiating the loss of individual identity in post-war corporate America. See also pages 71–75 for Schultz’s link between the corporate straitjacket of The Man in the Gray Flannel Suit and the rising sense of gangster influence across the country as expressed in the earlier film Force of Evil. 12. See Rachel Rubin’s Jewish Gangsters of Modern Literature (Urbana: University of Illinois Press, 2000) for a sustained look at some of the ways in which authors of the interwar period used the figure of the Jewish gangster in particular to critique the role of the individual in the capitalist context. 13. For one example, William Drury published an exposé shortly before his murder outlining the politics of the national crime cartel; he named Capone cousin Charlie Fischetti as the top man in Chicago, an estimate few historians share (William J. Drury and Don Petit, “Sinister Mafia Spreads Rackets Realm,” Miami Daily News, March 2, 1950). In similar fashion, the Tribune’s James Doherty, the paper’s leading organized-crime reporter in that era, asserted that Jack Guzik had taken over the reins of the gang from Frank Nitti around 1940 (James Doherty, “Al Capone Gang Broken, Gaming Ends: Courtney,” Tribune, October 4, 1942). Those are only two examples of a phenomenon legion across the history of the Syndicate/Outfit: the claim by outsiders to know the structure of the mob. It’s difficult enough to determine that structure in retrospect, and even then such charts rarely take into account the fluid nature of the organization behind crime. 14. See Roemer, Accardo, 95; and Eghigian, After Capone, 414, for two examples of the claim. 15. “2 Gangster Aids Step Into Case From Politics,” Tribune, September 27, 1947; and “National Crime and National Politics,” Tribune, October 1, 1947. 16. See Organized Crime in Chicago—1990 (Chicago: Chicago Crime Commission, 1990), 4.

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17. William Roemer, The Enforcer: Spilotro—The Mob’s Man over Las Vegas (New York: Donald I. Fine, 1994), 47. See also Roemer, Man against the Mob, 168. 18. Roemer, Man against the Mob, 29 and 306; and Roemer, Accardo, 182–83. 19. Alex testimony, 938–40. 20. Roemer, Man against the Mob, 29. 21. See Russo, Outfit, 99–102; and Touhy and Brennan, Stolen Years. 22. “Mob’s Murray Humphreys Dies,” Tribune, November 24, 1965. 23. “Report Mob Promotes Alex,” Tribune, November 26, 1965. 24. “Girls’ Charges Convict Inn Owners,” Tribune, February 17, 1922; see also Bergreen, Capone, 90; and Schoenberg, Mr. Capone, 88–89. 25. “Torrio ‘Drag’ Frees Two White-Slavers,” Tribune, September 27, 1923. 26. “Harry Guzik, Gang Figure in Dry Era, Dies in Miami at 73,” Tribune, January 24, 1949. 27. See Wooddy, Frank L. Smith, for an extended consideration of that political moment. 28. See Kobler, Capone, 121–22 and Bergreen, Capone, 89–90; both give the year of the event as 1924, but I am convinced that they are in error and that the original Tribune dates are correct. 29. “Raid Bares Vice and Rum Super-Trust,” Tribune, April 7, 1925; Kobler, Capone, 121–22. 30. See “How the Tribune Obtained Profit Sheets of Gang,” Tribune, October 30, 1941, for the fullest version of the story about the ledgers in the oven. 31. Gilbert would subsequently be identified as one of the most corrupt police officials in the country. The Tribune’s Ron Grossman wrote an overview of his career on February 25, 2016, “Dan Gilbert: ‘The World’s Richest Cop.’” See also Russo, Outfit, 257–58. 32. “Bookie Scorns Gambling Probe; Gets Jail Term,” Tribune, November 28, 1941. 33. “Jack Guzik Now Is No. 1 Man of Gang Overlords,” Tribune, October 25, 1941. 34. “Syndicate Gangster Slain,” Tribune, March 22, 1950. 35. “Gang Chief Guzik Dies,” Tribune, February 22, 1956. 36. Bergreen, Capone, 90–91. 37. Lindberg, Gangland Chicago, 57–59. 38. “Start New War on Vice Trust,” Tribune, August 31, 1912. 39. For the 1st Ward ball, see Lindberg, Chicago by Gaslight, 130–34; and Wendt and Kogan, Lords of the Levee, 268–81. For Bloom’s march of the prostitutes, see Wendt and Kogan, Lords of the Levee, 82. 40. See Bergreen, Capone, 80–81; and Schoenberg, Mr. Capone, 44–49. 41. Schoenberg, Mr. Capone, 64–65; and Bergreen, Capone, 82–85. 42. Bergreen, Capone, 92. 43. For one example, see Schoenberg quoting old-time Syndicate hanger-on George Meyer. “I used to hate that man with a passion,” Meyer said of Guzik. “Everything he ate for a week you could see on his vest. And the B.O.!,” (Mr. Capone, 102). See also a 1944 news story casually editorializing that he entered court “Fat, 58, and flashily dressed,” Frank Cipriani, “Guzik Reported Kidnapped by Gang,” Tribune, April 14, 1944. 44. Bergreen, Capone, 154. 45. “Molly Picon Returning in Yiddish Play,” Tribune, April 12, 1942. 46. Kobler, Capone, 122. 47. Ibid. The quote, which has become central to the standard telling of Capone’s life, gets recorded slightly differently in the other major biographies of Capone. Schoenberg gives it as “G’wan back to your whores, you Dago pimp,” (Mr. Capone, 102), while Bergreen gives “Listen, you Dago pimp, why don’t you run along and take care of your broads,” (Capone, 112). 48. “‘Four Deuces’ Owner Heads Mystery Feud,” Tribune, May 9, 1924. 49. Bergreen, Capone, 358–60. 50. Schoenberg, Mr. Capone, 352–53. 51. In fact, Guzik served as an occasional adversary to the heroes of The Untouchables TV series that ran from 1959–1963. Portrayed by actor Nehemiah Persoff, he appeared in at least three episodes.

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52. William J. Drury and Don Petit, “Ragen Slain By Mobsters,” Miami Daily News, March 9, 1950. 53. William J. Drury and Don Petit, “Mob Cartel Menace Calls for Action By Federal Forces,” Miami Daily News, March 13, 1950. 54. “Gang Chief Guzik Dies,” Tribune, February 22, 1956. 55. Roemer, Man against the Mob, 52.

Notes to Chapter 10 1. Interview with Chris Gair. 2. “Cuban Official: Kennedy’s Assassination Part of Plot,” Palm Beach Post, November 28, 1993; the article spells “Cain” as “Gaines,” but most conspiracy theorist supporters seem to read it as “Cain,” and Richard Cain was a major Syndicate torpedo of the era. 3. Jack Shadoian, Dreams and Dead Ends: The American Gangster Film (New York: Oxford University Press, 2003), 4. Shadoian’s reading of the gangster as a figure representing the contradictions of a materialistic culture—on enticing us with wealth and possibility but also asserting that greed is sinful, has its roots most clearly in the pioneering cultural studies work of Robert Warshow, particularly his “The Gangster as Tragic Hero,” (Robert Warshow, The Immediate Experience: Movies, Comics, Theatre and Other Aspects of Popular Culture [Garden City, NY: Doubleday, 1962], 127–34). 4. Warren Commission Report, 5:200. 5. Ibid., 5:204. 6. Ibid., 14:410. 7. The testimony makes clear elsewhere (see Report of the House Select Committee on Assassinations, 9:945) that the reference is to Benny Zuckerman, the “Zukie the Bookie” who was killed around the same time as Willie Tarsch. 8. Ibid., 9:951; for the record, there seem to be no ties between Jack Ruby and Benny Zuckerman. 9. Ibid., 9:950. 10. Ibid., 9:957. 11. Ibid., 9:959. 12. In answer to the more direct inquiry about whether Ruby ever called him, Patrick said no, that he and Ruby had had no dealings for years, but he did suggest that Ruby might have called Yaras. You can almost see the interviewer perk up at the response. “You are saying that Yaris [sic] knew Ruby?” he followed up. Patrick then explained that Yaras and Ruby had sometimes gone to the fights together, that they were also old acquaintances from Lawndale, and there wasn’t much more to it than that. Ruby’s sister told the Warren Commission that Yaras’s brother Sam had visited Ruby in Dallas in the early 1950s, but that too was a thin thread (Warren Commission Report, 14:444; as part of her testimony, Eva Grant declared, “I knew of more than he knew,” suggesting that she was more aware of the reputations of Chicago gangsters than Ruby was). Yaras had already denied having any relationship with Ruby (Yaras FBI file, report dated January 21, 1965, p. 48). In his interview with the FBI on December 5, 1964, Yaras did acknowledge that his brother Sam had lived in Dallas for a time—leaving open the possibility that he’d visited Ruby—but he did not imply they were connected either, and with Yaras dead five years before, there was no way to follow up. The implication was that Ruby was friends with Yaras just as he was friends with Barney Ross. Ruby was the sort who looked up to charismatic and powerful others. In the same way that he famously befriended the Dallas police officers who, because of such familiarity, let him get close to Oswald, he sought out people he wanted to be like. 13. Ruby was involved for a time with a scrap metal union where he acted as hired muscle for president Leon Cooke. Cooke was murdered in 1939, and his local came under the control of Paul “Red” Dorfman (William Moore, “Probers Hear of Dorfman’s Link to Hoffa,” Tribune,

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209

January 30, 1959), father of Allen, who would be one of Patrick’s shakedown victims in the early 1970s. The bottom line of that experience seems to be that Ruby, in his one foray into organized crime, ‘backed the wrong horse.’ With Cooke’s murder, he had no organization left to be loyal to, and he moved to Dallas not long thereafter. 14. Patrick FBI file, report dated September 30, 1958, p. 14–15; see also Patrick FBI file, report dated December 2, 1958, p. 11, for FBI concerns that the source did not come forward again. 15. Interview with Chris Gair. 16. Lacey, Little Man 252–59; for Yaras’s link to Lansky through Vincent Alo, see Yaras FBI file, report dated May 7, 1965, 26–27. 17. Patrick FBI file, report dated September 30, 1958, p. 12. 18. Ibid., report dated September 30, 1966, p. 3; and July 8, 1971, p. 71. 19. Ibid., report dated August 1, 1958, p. 5–6. 20. Ibid., report dated July 22, 1969, cover page B. 21. Yaras FBI file, report dated July 28, 1964, p. 43. 22. William Moore, “Seeks Ruling on ‘Capricious’ Probe Dodgers,” Tribune, December 18, 1957. 23. Yaras FBI file, report dated January 21, 1965, pp. 38 and 40. 24. Ibid., p. 45. 25. William Moore, “Seeks Ruling on ‘Capricious’ Probe Dodgers,” Tribune, December 18, 1957. 26. Yaras FBI file, memo dated April 28, 1967. 27. Bill Moeser, “Mario Slugged; Who He?,” Miami Daily News, February 8, 1959. 28. Yaras FBI file, report dated July 28, 1964, p. 43. 29. Patrick FBI file, report dated July 8, 1971, p. 43. 30. Ibid., p. 51. 31. Ibid., report dated March 22, 1974, cover page B. 32. Yaras FBI file, report dated January 21, 1965, p. 8. 33. Milt Sosin, “U.S. Excludes Gambler Tossed Out By Cuba,” Miami Daily News, March 1, 1953. 34. Milt Sosin and William Tucker, “Racketeer is Shot Dead Here,” Miami Daily News, October 31, 1967. 35. Patrick FBI file, report dated March 22, 1974, cover page B. 36. Dick Holland, “Mobster’s Son Slain in Home,” Miami Daily News, April 19, 1974. 37. “Ex-Police Chief Charged in Murder,” St. Petersburg, FL Tampa Bay Times, December 15, 1977; and “Jury Deadlocked Over Murder Trial,” Palm Beach Post, April 2, 1978. 38. Yaras FBI file, report dated September 2, 1965, p. 1. 39. Pileggi, Casino, 24. 40. Julie Weitz, “Finding Lefty,” New Voices [American Jewish Life Magazine] (January 2004). 41. Pileggi, Casino, 25. 42. Ibid., 48–50. 43. William Moore, “Oregon Player Tells of $10,000 Bribe Offer,” Tribune, September 9, 1961; and Pileggi, Casino, 64–67. 44. Robert Wiedrich, “Chicago Hoodlums Prefer Florida Heat,” Tribune, January 21, 1966. 45. Patrick FBI file, report dated January 29, 1969, cover page. 46. Roemer, Enforcer, 159–60; and Pileggi, Casino, 316–17. 47. Robert Macy, “Former Mobster’s Slaying Is the Talk of Las Vegas,” Reno Gazette-Journal, January 10, 1997. 48. “Murder of Chicago Hood Foretells Power Grab by the Los Angeles Mob,” Illinois Police and Sheriffs News, June 4, 1997. 49. “Blitzstein Always ‘Second Fiddle’ to Spilotro,” Las Vegas Sun, January 8, 1997. 50. John O’Brien, “Spilotro Associate Shot to Death in Las Vegas,” Tribune, January 9, 1997.

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51. “Murder of Chicago Hood Foretells Power Grab by the Los Angeles Mob,” Illinois Police and Sheriffs News, June 4, 1997. 52. “Blitzstein Always ‘Second Fiddle’ to Spilotro,” Las Vegas Sun, January 8, 1997.

Notes to Chapter 11 1. Schoenberg, Mr. Capone, 216. 2. Ibid., 219–20; Bergreen, Capone, 315. 3. Final report of the Permanent Subcommittee on Investigations’ examination into organized crime and narcotics, 1969, quoted in John L. McClellan and G. Robert Blakey, “The Organized Crime Act (S. 30) or Its Critics: Which Threatens Civil Liberties,” Scholarly Works, Paper 171, 1970, p. 60. 4. Frank Spiering, The Man Who Got Capone (Indianapolis, IN: Bobbs-Merrill, 1976). 5. The 1932 Scarface film makes light of that practice when it has Camonte’s lawyer, “Epstein,” explain how the process works and then later has Camonte invoke it in an accent suggesting he barely understands the principle he’s claiming in his own defense. 6. McClellan and Blakey, “Organized Crime Act,” 141. 7. Tom Wicker, “In the Nation: The Crime Fighters’ Folly,” New York Times, June 11, 1970; “Against the Law,” New York Times, June 22, 1970; Jeff Gerth, “U.S. Expanding Use of ’70 Crime Statute,” New York Times, December 8, 1978; and William Safire, “The End of RICO,” New York Times, January 30, 1989, for a handful of examples. 8. Arnold H. Lubasch, “Immunity Part of ’70 Crime Act Ruled Invalid By Federal Judge,” New York Times, January 30, 1971. 9. Patrick FBI file, report dated December 31, 1970, cover page D. 10. Richard Stengel, “The Passionate Prosecutor, U.S.,” Time, June 24, 2001. 11. Roemer, Enforcer, 183. The two turncoat witnesses from before 1985 that he refers to are Joe Valachi of New York and Jimmy Fratianno of Los Angeles. 12. John O’Brien and George Bliss, “Mob Generation Gap Endangers Tony Accardo Pals,” Tribune, May 1, 1977. 13. Ibid. 14. John O’Brien and Ronald Koziol, “New Generation of Mob Leaders Rises in Chicago,” Tribune, March 30, 1986. 15. For the completists, north-suburban bookmaker Michael Posner, regularly listed as a soldier or associate in the Outfit of the l990s, was the son of bookmaker Bernard “Pipi” Posner, reputedly a longtime lieutenant of Syndicate boss Ralph Pierce. See “Accuse 3 Seized with Unopened Safe in Chase,” Tribune, July 3, 1951; “Seek Gaming Collector for Murder Quiz,” Tribune, May 8, 1963; Lee Strobel, “Two Indicted in Probe of Mob, Adult Bookstores,” Tribune, July 29, 1976; Bob Sector and Phillip J. O’Connor, “Porno Landlord Blames Plight on the Crosstown,” Tribune, July 7, 1977. 16. Patrick testimony in Gus Alex trial, 989. 17. Ibid., 1026. 18. Ibid., 996 and 1220. 19. Art Petacque, “Lawyers, CPAs Waiting to Inherit Chicago Mob,” Sun-Times, July 12, 1987. 20. Johnson, History of Violence, 275–76. 21. “Two Indicted in Bomb Plot,” Tribune, February 17, 1978. 22. Patrick testimony in Gus Alex trial, 947. 23. Ibid., 991. 24. Ibid., 989. 25. Ibid., 990. 26. Rosalind Rossi, “Extortion No Easy Job, Con Tells Jury,” Sun-Times, September 15, 1992. 27. Constanza Montana, “Slain Man, 73, May Be Linked to Mob,” Tribune, November 23, 1988, John O’Brien and Ronald Koziol, “Ex-Bookie’s Killing May Be ‘Message,’” Tribune,

NOTES TO C H A P TE R 1 2

211

November 24, 1988, and Ronald Koziol, “Dinner Reservations Become Another Puzzling Part of Slaying,” Tribune, December 29, 1988. 28. William Recktenwald, “City’s Violent Summer Continues,” Tribune, July 2, 1990; and William Recktenwald and John O’Brien, “Officials Probe Records of Slain Bookmaker,” Tribune, July 3, 1990. 29. Patrick testimony in Gus Alex trial, 1660. 30. Ibid., 1635. 31. Ibid., 983–86. 32. Patrick FBI file, report dated March 15, 1972, p. 3. 33. Roemer, Man against the Mob, 35–36 and 302. 34. The clearest sign of the Outfit’s continued capacity for corruption in Chicago at a high level came in 1992 when Operation Gambat targeted, among others, longtime 1st Ward Syndicate figure Pat Marcy, former state senator John D’Arco, and 1st Ward alderman Fred Roti, in a case that proved they’d fixed the 1977 trial of noted torpedo Harry Aleman. See Robert Cooley and Hillel Levin, When Corruption was King: How I Helped the Mob Rule Chicago, Then Brought the Outfit Down (New York: Carroll and Graf, 2004), for the most sustained account. 35. Patrick testimony in Gus Alex trial, 1604–11. 36. Ibid., 1610. Chris Gair recounts that LaValley, a large and violent man, was simply too successful at intimidation. A number of his victims panicked after he threatened them and, against the presumed code of the quasi-legal businessperson, turned to the FBI for help. That evidence helped prosecutors “turn” LaValley, who went on to become a consequential witness against Gus Alex and Sam Carlisi alongside Patrick. 37. John Kass, “Outfit Enforcer Stays Mum, Takes Any Secrets Back to Cell,” Tribune, September 18, 2014. 38. From interview with Chris Gair. 39. Patrick testimony in Gus Alex trial, 1082. 40. Ibid., 1083 (for Marcello), and 1104–5 (for Marcy). 41. Ibid., 1099. Patrick’s elision of “for” and “from” would become a pivotal point during the subsequent trial (see Tribune, October 2, 1992), but Patrick referred to it as “a little error,” and the original transcript does record him saying both, intimating that the “from” was a correction while he was still talking to Alex. 42. See Patrick testimony in Gus Alex trial, 982, for a description of Zappas’s role as union head. 43. Ibid., 1143–49. 44. Matt O’Connor, “Reputed Mob ‘Street Crew’ Chief, Accardo Buddy Face U.S. Charges,” Tribune, December 19, 1991.

Notes to Chapter 12 1. There was, in fact, a slew of comedies with that premise in the late 1980s and early 1990s. See Zev Chafets’s 1991 novel, Inherit the Mob (New York: Random House), where a journalist learns he has inherited his Meyer-Lansky-like uncle’s share of the national crime syndicate; The Marrying Man (1991), where Bugsy Siegel requires a young man to marry his mistress as punishment for sleeping with her; Miller’s Crossing (1990) where Jewish gangster Bernie Bernbaum double-crosses everyone he meets; and Pulp Fiction (1994), where apparently Jewish Winston Wolfe is the archetypal older gangster whom the younger ones turn to in a crisis. 2. Matt O’Connor, “Alex Lawyer Rips Key U.S. Witness,” Tribune, September 10, 1992. 3. “Old Pals Facing Off in Mob Case,” Tribune, September 8, 1992. 4. See photograph accompanying Tribune story, “Extortion Viction Recounts Terror,” September 11, 1992. 5. Tribune reporter Robert Blau captured that anomalous sense in a story he wrote about a visit with a group of older Jewish men at a north-side community center. The alte kockers were

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all in with Patrick, whom they saw as “a 78-year-old man who was nice to people his whole life.” One complained, “Guys like that they go after?” Another, sighing “oy vay,” came out with a sarcastic, “God bless America.” Among themselves, they were serious, sharing—as the article reminds us—their youth in the Jewish ghettos, but it was also clear that the paper was presenting them as exotics, as unlikely characters for the rest of us to be amused by (“To Old Pals, Lenny Just a Gentle Man,” Tribune, December 22, 1991). 6. Alex testimony, 928. 7. Ibid., 941. 8. Ibid., 942. 9. Ibid., 943. 10. Ibid., 944. 11. Ibid., 945. 12. David Mendell, “Julius Lucius ‘Lucky’ Echeles, 83, High-Rolling Defense Lawyer,” Tribune, September 6, 1998. 13. From interview with Chris Gair. 14. Alex testimony, 937–38. 15. Ibid., 1056. 16. Ibid., 946. 17. Ibid., 952. 18. Ibid., 952–55. 19. Ibid., 958. 20. Ibid., 959–60. 21. Gotti was finally convicted in April 1992, roughly five months before the Alex trial and Patrick’s first time on the witness stand. 22. Alex testimony, 1047. 23. Ibid., 1162. 24. Ibid., 1168–69. 25. Ibid., 1172. 26. Ibid., 1224. 27. Ibid., 1173–76. 28. “Reputed Mobster Gets 16 Years Prison,” Woodstock, IL Northwest Herald, February 21, 1993). 29. John O’Brien, “Imprisoned Mobster Sam Carlisi, 75,” Tribune, January 4, 1997. 30. Matt O’Connor, “Reputed Mobster Chief is Sentenced to 12 Years,” Tribune, March 9, 1996. 31. John O’Brien, “Imprisoned Mobster Sam Carlisi, 75,” Tribune, January 4, 1997. 32. One of Gair’s New York colleagues, James Comey, himself a onetime assistant US attorney bringing cases against organized-crime figures, offers the same assessment about the state of post-RICO organized crime. “There are still people who call themselves Italian Mafia, but it is a motley collection of criminals that would embarrass Lucky Luciano,” James Comey, A Higher Loyalty: Truth, Lies, and Leadership (New York: Flat Iron Books, 2018), 28. 33. Rosalind Rossi, “Prosecutors Say Patrick Lied as Mob Informant,” Sun-Times, April 15, 1993. 34. Sharon Cotliar, “Mobster with Alzheimer’s Found Unfit for Murder Trial,” Sun-Times, November 27, 1996.

Notes to Afterward 1. Binder, Beer Wars, 109–10. 2. “Miller’s ‘Joints’ Shut Once More,” Chicago Daily News, June 2, 1928.

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INDEX

A Abrahams, Fannie, 82 Abrahams, Manny, 7, 50, 68, 77–78, 78–82, 90, 104, 170, 199n10; as alderman, 78–79, 81; campaign for Cook County Commissioner, 79; as clerk for courts, 79–80; criminal vs. citizen, 79–80; death of, 82; gambling, 81; as saloon owner, 79; as state representative, 80; violence and, 81; vote for Republican Lorimer, 80; work for peddlers, 81 Abrahams, Morris, 82, 104 Accardo, Tony, 5, 10, 38, 40, 45, 47, 64, 75, 119, 126–27, 150, 173 Acher, John “Doc”: murder of, 73–74 Adam, Sam, 163–64 African Americans, 27, 84, 87, 149 After Capone (Eghigian), 11 Aiello, Joe, 172, 173 Aiuppa, Joey “Doves,” 38, 40, 127, 140, 150 Albany Park (neighborhood), 8, 142 Al Capone’s Beer Wars (Binder), 169 Alcock, Thomas, 19 Alderisio, Felix “Milwaukee Phil,” 46, 116, 117, 118, 127, 205n34 Alesia, James, 163 Alex, Gus, 5–6, 38, 40, 41, 43, 44, 45–46, 47, 98, 108, 119, 127, 128, 132, 148, 150, 152, 153, 154, 173; trial to bring down “Outfit,” 157–67; wire on, 155–56 Angelini, Donald, 142, 149 Anixter, Julius “Lovin’ Putty,” 4, 5, 7, 13, 25, 52, 53, 58, 59, 61–66, 62, 72, 78, 93, 173; connections with police, 61; connections with politicians, 62; creating networks, 61; gambling, 62–65; roots in Maxwell Street, 62; story of name, 61–62, 196n119 Anixter, William “Irish,” 63 Annenberg, Moses, 119, 173, 205n41 Arvey, Jacob, 7, 14, 18, 25, 53, 60, 65, 69–70, 75, 78, 79, 90–98, 106, 120, 125,

171, 173; as alderman, 91; balancing crime and reform, 90–98, 95, 97–98; connection with organized crime, 94–95; connection with politicians, 90; family background, 91; military service, 94; as a Republican, 92–93; ward workers, 71 Asbury, Herbert, 188n26

B Backstage Lounge, 40 Barr, Lena, 62 Barrett, George, 66 Barry, Dave, 54 Battaglia, Sam “Teets,” 46, 127 Beaux Arts Cafe, 56 Belcastro, James the “Mad Bomber,” 95 Bell, Daniel, 9 Bergreen, Laurence, 6, 131 Biles, Roger, 190n31 Binder, John, 29, 169 Black Angus restaurant, 44 Bliss, George, 38 Blitzstein, “Fat” Herbie, 142–44, 173 Block, Alan, 4, 24 Block, Harry, 49, 173 Block, William, 95–96, 119–20, 121, 174 Bloom, Ike, 174 Bollotin, Henry, 63 bootlegging, 5, 16, 28, 82; distribution of alcohol, 24; under Miller, 49 boxing, 49, 54, 61, 193n48, 193n52, 201–2n1 Brin, Sam, 86 Buccieri, Fiore “Fifi,” 46, 118 Byrne, Jane, 43

C Cagney, James, 145 Cagnina, Sam, 141 Caifano, Marshall, 38, 127 Cain, Richard, 135, 208n2 Campagna, Tony, 95 Capone, Al, 6, 7, 128, 145–46, 174; friendship

218

with Guzik, 131–32; income tax laws, 123, 132; murder of Howard, 131–32; quote, 207n47; as scarface, 23, 145; sports and, 74; Yiddish culture and, 131 Capone, Frank, 17 Capone, Matt, 171 Capone gang, 17, 64, 72, 85. See also organized crime in Chicago Carlisi, Sam, 5–6, 10, 127, 135, 148, 155, 174; trial to bring down “Outfit,” 157–67 Carroll, John, 14 Carroll, William, 14, 15 Casino, 16, 127, 143 Castro, Fidel, 138 Caverly, John, 56 Central-West Beer Distributors, 13 Cermak, Anton, 7, 52, 53, 56, 90, 94, 124, 174; 1st, 79; assassination, 56, 194n75; control of organized crime, 123; fusion of crime, politics, community, 52–53; lack of corrupt support, 123; neighborhood organizations, 123 Cerone, Jackie, 118, 150 Charles, Ezzard, 54 Chicago American, 82 Chicago Confidential, 121 Chicago Crime Commission, 70, 96, 121–22, 171, 203n36 Chicago Herald American, 121 Chicago Jews: demographics, 4; forgetting legacy, 170; neighborhoods, 4, 13–15, 23–35; neighborhood shifts, 8, 10, 32–34 Chicago police department, 37, 38, 55–56; graft in, 56–57; “Hoodlum Squad,” 56, 123; public-enemies list, 114; raids, 39–40, 63, 64, 65–66. See also law enforcement Chicago politicians: connections with organized crime, 7, 52–53, 62, 79, 90, 93; distancing from organized crime, 94, 97–98; gangster/politician hybrid, 125. See also Jewish politicians Chicago Sun, 71 Chicago Sun-Times, 18, 150 Chicago Tribune, 28, 32, 38, 39, 40, 45, 62, 70, 79, 80, 90, 91, 120, 129, 132, 150 Cicero, Illinois, 17 Clarendon Beach, 50 Clark, James, 83 Clinnin, John V., 84

I NDE X

Cochran, Johnnie: trial as performance, 159 Cohn, Art, 185n1, 195n103 Collier’s magazine, 52, 53 Collins, Max Allan, 55 Colosimo, “Big” Jim, 10, 24, 130, 131, 174 Comey, James, 212n32 Cominskey Park, 54 Connection Guys, 127–33, 132 Connelly, Capt. Thomas, 120–21, 124, 132, 174 Continental Press, 119 Cooke, Leon, 208–9n13 Cooney, Dennis, 66 Coppola, Mike “Trigger,” 142 Corsino, Louis, 11 Cosmopolitan Laundry, 41 Costello, Tom, 62 Coughlin, “Bathhouse” John, 7, 125 Cowan, Arthur “Boodie,” 47, 117, 161 Cowan, Mike, 161 Cuba, 138 Cutler, Irving, 3, 8, 9, 27

D Daily News, 54 Daley, Richard J., 68, 97, 190n31 D’Andrea, Phil, 95 Dann, Louis, 18, 23n34, 65, 94, 174 D’Arco, John, 125, 211n34 Davidian, Abraham, 118 Davis, Sam, 28 Day Book, 62 Defender, 87 Demaris, Ovid, 20 Democratic machine, 5, 7, 11, 42, 53, 60, 65, 68, 69, 74, 90–94, 93–94, 121; discipline in machine politics, 90–91; distancing from organized crime, 94; fusion of crime, politics, community, 52–53; links to gangsters, 74–75; patronage, 42; saloons and politics, 79. See also Chicago politicians Dempsey, Jack, 4, 54 Deneen, Charles, 87 DeNiro, Robert, 16 Detroit, Michigan, 138 Deutsch, Sidney, 93 Dever, Michael, 91 Dever, William, 17, 128 DiFronzo, John, 149 discipline in machine politics, 90–91 Disco Demolition, 149

I NDE X

Dorfman, Allen, 44, 174, 190n37 Dorfman, Paul “Red,” 44, 208n13 Dorman, Louis, 118 Douglas, Paul, 90, 202n4 Douglas Park, 8, 51, 59 Drucci, Vincent “Schemer,” 30, 82, 83 Druggan, Terry, 82 Drury, Lt. William, 110, 120–21, 124, 129, 132, 159, 160, 174 Duffy, John, 195n101

E East Side-West Side: Organizing Crime in New York, 1930–1950 (Block), 4 Echeles, Julius, 160 Edelstein, Sam, 193–94n59 Edmille gym, 193n48 Egan, Dennis, 57 Eghigian, Mars, 11 Ehrlich, Barney, 63 Eisen, Max, 55, 59, 72, 85, 170, 174 Eller, Emanuel, 78, 83, 84, 175, 200n43 Eller, Morris, 4, 7, 50, 53, 54, 58, 68, 78, 82–86, 92, 105, 169, 170, 175; bootlegging, 82; campaigns workers, 85–86; family background, 82; as “gobetween” rival gangs, 85; influence with courts, 86; influence with police, 86; murder of Granady, 86, 93, 95; patronage, 84; political offices, 84; relation with Zuckerman, 85; as a Republican, 84; stories about, 82–83; violence in campaigns, 86–87, 93; ward committeeman, 84, 86–87 Ellroy, James, 121 Elrod, Arthur X., 7, 14, 20, 25, 75, 106, 120, 164, 175, 203n36; connections with organized crime, 94–97; death of, 98; murder of Zuckerman, 10 El Rukins gang, 149 English, Butch, 127 Epstein, Albert, 50 Epstein, Samuel, 93 Ettelson, Samuel, 95, 203n37 extortion, 43–45, 151, 154, 161

F Factor, Jake “the Barber,” 94, 175 Family Secrets trial, 166 faro, 188n26

219

FBI. See law enforcement Feinerman, David, 86 Fischetti, Rocco, 116, 121 Fitzel, Mike, 115 Fitzmorris, Charles, 57 Flack, Joseph, 31 Foster, Frank, 85 Foucault, Michel, 91 Fratto, Rudy “the Chin,” 154 freedom of assembly, 147 Fried, Albert, 4 Friedman, Sailor, 55, 59

G Gair, Chris, 148, 151, 155, 189n12, 211n36; trials of Alex and Carlisi, 157–67 Gallico, Paul, 54, 58 gambling, 186n1 legalized gambling, 42; state lottery, 42; taxation and, 42 New York Jets Super Bowl, 161 New York Mets World Series, 161 organized (illegal) gambling, 5, 13, 19, 27; Abrahams and, 81; Anixter and, 62–65; approval under Thompson, 89; Beaux Arts Cafe, 56; bookmaking operations, 43, 130; changes over the years, 158; distribution of gambling concessions, 24; expenses for protection, 129–30; gambling centers, 40; Miller and, 49–50; Patrick and, 39–40, 42, 43, 158; sports and, 74; Zuckerman and, 69–70, 89, 115–16 stuss, 28, 188n26 Gang, The (Thrasher), 186n11, 192n37 Gangland Chicago (Lindberg), 11 gangster loophole, 146, 147 Garcia, Ismael, 141 Garfield Park, 8, 51 Giancana, Sam, 38, 116, 120, 126–27, 175 Gilbert, Daniel “Tubbo,” 129 Gio, Nicholas, 151, 154–56 Gioe, Charles, 95 Giuliani, Rudy, 148 Glazier, Benjamin, 14, 61, 65, 73, 95, 116, 175 Gleason, James, 63 Glick, Herman, 113, 114, 160, 164, 175 Glickman, Milton, 160 Godfather, The (films), 148, 149 Goodman, Manny, 55 Goodman, Philip, 152

220

Gotti, John, 149, 162 Granady, Octavius, 86–87, 175; murder of, 87, 93, 95, 113 Green, Harry G., 63, 196n127 Green Mill bar, 172 Griffin, Burt W., 136 Gross, Charles, 117, 160 Grossman, Leonard, 69, 71 Grossman, Ron, 68 Gusenberg, Frank, 83 Guzik, Alma, 128, 130, 175 Guzik, Harry, 66, 112, 128, 130–31, 175 Guzik, Jack, 7, 64, 75, 103, 116, 119, 120, 149, 155, 169, 175, 207n43, 207n51; as Connection Guy, 128–33; connections with police, 129; death of, 133; family background, 130; friendship with Capone, 131–32; as schlub, 133 Guzik, Joseph, 130 Guzik, Max, 130 Guzik, Sam, 130

H Hadesman, Charles “Chick,” 55, 59, 175 Haidelovich, Adam, 29 Harrison, Carter, Jr., 81, 82, 90, 125, 130, 176 Hayes, Howard, 128 Healy, Charles, 62, 63 Hecht, Ben, 23, 24, 25, 26, 57 Hennesy, William “Spike,” 56 Herald and Examiner, 63, 64 Herald Examiner, 33, 59 Herman Sales, 41 History of the Jews (Meites), 3, 77–78 Hochstein, Harry, 85 Hoffa, Jimmy, 44 Hoffman, Peter, 82 “Hoodlum Squad,” 56, 123 Hoover, J. Edgar, 37, 122 House Select Committee on Assassinations, 135 Howard, Joe, 131 Hughes, Michael, 30, 65 Humboldt Park (neighborhood), 50 Humphreys, Murray, 46, 64, 75, 94, 119, 127, 128, 129, 132, 133, 176 Hyde Park (neighborhood), 8, 172

I Illinois Crime Survey, 25, 186n11 immigrant experience, 33, 67

I NDE X

income tax laws, 123, 146 Infelise, Rocco, 127, 166 Insull, Samuel, 91; graft, 91–92 Irey, Elmer, 146, 159

J Jacobs, Ben, 85 Jacobson, Joey, 115 Jazz Singer, The, 33 Jewish Daily Courier, 52 Jewish gangsters, 188n26; alliances with politicians, 7; forgetting legacy, 170; histories of in Chicago, 3; Jewish Prohibition gangsters, 6; lack of control, 10; lack of multigenerational organization, 9; North side vs. Lawndale, 59; relationship with neighborhood, 8–9, 10; stuss, 188n26; threads of a single story, 6–7, 10–11; “20th Ward Group,” 54, 85, 169, 201n51; violence in campaigns, 86–87, 93 Jewish organized crime (confederation model), 5, 7, 23–35; as subcontractors, 13, 16–18 Jewish organized crime (corporate model), 7, 10, 16–17, 26 Jewish organized crime (independent model), 7, 10, 23–35 Jewish politicians, 7, 10, 25, 50, 52–53, 90; fusion of crime, politics, community, 52–53; protectors of mob, 27 Jewish Record, 27 Jews of Chicago, The (Cutler), 3 Johnson, Wayne, 122, 151 Johnson, William, 61, 64 Joker Is Wild, The (Cohn), 3, 185n1, 195n103 Jones, Edward P., 118

K Kaplan, Bill, 142 Kaplan, Sam, 29, 85, 201n48 Kaufman, Julius, 85, 201n54 Keane, Thomas, 43 Keefe, Rose, 11 Kefauver, Estes, 37 Kefauver Commission, 122 Kelley, Edward, 120, 124, 125 Kenna, Mike “Hinky-Dink,” 7, 68, 79, 125, 131, 176; 1st, 79 Kennedy assassination, 5, 135–38, 208n2,

I NDE X

208n12 Klass, Abe, 85 Klass, Martin, 85 Klass, Nathan, 85 Klein, Louis, 63 Klenha, Joseph, 17 Kobler, John, 131 Kolven, Hershey, 160 Korshak, Marshall, 67 Korshak, Sidney, 67, 176 Kosher Capones, The (Kraus): sources, 181–83 Kostner, Joseph, 57 Krotish, Harry, 117, 160, 165, 176

L L. A. Confidential, 121 Lait, Jack, 121 Lake, Frankie, 82 Lakeview (neighborhood), 98 Landesco, John, 25, 55, 182, 186n11, 187n12 Lang, Harry, 56, 123; shooting of Nitti, 124 Lansky, Meyer, 138 Larman, Frank, 28, 176 Larman’s (gambling), 28, 63 Lasky, Morris “Mushie,” 39 Las Vegas, 44, 127, 142–44, 150 LaValley, James, 151–52, 154–55, 164, 176, 211n36 law enforcement, 10; conspiracy, 147–56; FBI, 37–38, 117–18, 122, 127, 135, 137, 138–44, 150, 154–56; freedom of assembly, 147; gangster loophole, 146, 147; raids on Patrick, 37–38; RICO (Racketeer Influenced and Corrupt Organizations), 11, 43, 47, 147–56, 158–57 passim; trial as performance, 159. See also Chicago police department Lawndale, 4, 7, 8, 13–14, 49–66, 170–71, 192n29; collapse of independent gangsters, 13–21; criminality versus community, 53–58; Polish gangs, 51–52; shift from Maxwell, 49–53, 58–61, 93, 130 Lazarus, Victor, 152 Levee, The, 27, 28, 82, 130, 131 Levin, Hymie “Loud Mouth,” 66, 116, 119, 176, 181 Levine, Ira “Sonny,” 169–70 Levine, Jerry, 169–70 Lewis, Ben, 117 Lewis, Joe E., 3, 172

221

Lindberg, Rich, 11 Little Big Dollar stores, 41 Little Caesar, 145, 147 Loesch, Frank, 124 Lombardo, Gus, 24 Lombardo, Joey “the Clown,” 151 Lombardo, Robert, 11 Loren-Matese, Betty, 17 Lorimer, William, 63, 80 Los Angeles, California, 139 Luciano, Charles “Lucky,” 176 Lufman, Eugene “Yudie,” 41, 43, 46, 148, 176 Luxor steam baths, 38 Lyle, John H., 24–25, 124

M “machine,” 90–91 Mackenberg, Meyer, 85, 113 Maimi, Florida, 138 Mangano, “Dago” Lawrence, 16, 66, 75, 116, 158, 176 Man in the Gray Flannel Suit, The, 126, 206n11 Man Who Got Away, The (Keefe), 11 Marcello, James, 155, 161, 165, 176 Marcy, Pat, 125, 155, 166, 211n34 Marigold Gardens, 172 Marovitz, Abraham, 61, 106, 196n14 Martin, Jim, 155 Maxwell Street, 4, 7, 8, 23–35, 111, 170; bootlegging, 28; changes from 19th century to closing of Levee, 27, 84; evidence of confederation, 27; gambling, 27, 28; prostitution, 27; shift to Lawndale, 49–53, 58–61, 93, 130 McClellan, John, 37 McClellan Commission, 122, 142, 147 McDonald, Mike Cassius, 7, 177 McErlane, Frank, 29 McGee, Geri, 143 McGeoghegan, Danny, 114 McGurn, Jack, 172 McInerney, Philip, 72 McLaughlin, John “Bathhouse,” 68 Meites, H. L., 3, 77–78, 82 Mejia, David, 156 M&E restaurant, 50, 61, 64, 192n26. See also R&K restaurant Messino, Willie “the Beast,” 154 Meyer, George, 207n43 Meyers, Yussie, 44, 161 Miami, Florida, 138–42

222

Miami Daily News, 121 Miller, Al, 7, 55, 177, 193–94n59 Miller, August, 62 Miller, Ben, 193–94n59 Miller, Davey, 4, 5, 7, 14, 25, 27, 49–61, 63, 64, 78, 85, 89, 93, 102, 123, 170, 171, 177, 195n103, 202n3; bootlegging, 49, 59; boxing interests, 49, 193n48, 193n52; as “connected,” 58–60; criminality versus citizenship, 53–58; demise of power, 61; Eller connection, 89; family background, 49, 54–58, 193– 94n59; gambling, 49–50, 58–61, 158; illegitimate business interests, 49–50, 58–61, 59, 158; legitimate business interests, 49; manipulation of news coverage, 59; murder attempt of at LaSalle Theater, 59–60; political connections, 50, 58; as protector of Jewish citizens, 50–52; race attitudes, 192n38; racketeering, 59; Republican party and, 53; rise in power through confederation, 58–61 Miller, Davey “Yiddles,” 177, 192n38 Miller, Esther, 193–94n59 Miller, Harry, 55–56, 123, 124, 177, 193–94n59, 194n71 Miller, Hirschie, 27, 49, 56–58, 85, 102, 169, 177, 193–94n59, 195n101; attempted murder of, 57–58; bar owner, 60; cleaners business, 57–58; innocent verdict, 57; jail time, 60; murder of police, 56–57; racketeering, 57–58 Miller, Jack, 193–94n59 Miller, Max, 3, 55, 59, 102, 177, 185n1, 193– 94n59, 195n103; murder attempt of at LaSalle Theater, 59–60, 185n1 Miller, Sarah, 193–94n59 Miller, Shelley, 45 Miller, Sylvia, 192n38 Mincer, Al, 163 Moran, George “Bugs,” 17, 19, 73, 83, 145, 177 Mortimer, Lee, 121 Morton, Paul, 85, 201n53 Morton, Samuel “Nails,” 4, 56, 57, 145, 169, 177, 183, 201n53 Mulcahy, James “Pluck,” 56 Multiple Sports News Service, 142 Muni, Paul, 145 Murder, Inc., 117 Murphy, Eddie, 116–17, 160, 177; murder of

I NDE X

Zuckerman, 15–16 myth of Mafia, 149, 212n32. See also Scarface (film)

N Nash, Pat, 125 Neighborhood Outfit, The (Corsino), 11 Neistein, Bernard, 67, 78, 177; political connections, 68; violent projection, 68–69 Nelli, Humbert, 24 Ness, Eliot, 146, 159 Newberry, Ted, 94, 124, 177 New York Confidential, 121 New York Murder, Inc., 117 Nicoletti, Charles, 117, 149, 205n34 Nitti, Frank, 56, 64, 123, 129, 177; shooting of, 124 North Lawndale, 51. See also Lawndale North Side Gang, 17, 19, 29, 56, 59–60, 64, 72, 73, 85, 124, 145

O O’Banion, Dean, 3, 17, 24, 56, 68, 170, 177–78; attempted murder of Millers, 59–60, 185n1; murder, 29–30 O’Brien, John, 39 O’Hara, Ronald, 47 O’Kane, James, 9, 199n72 Operation Gambat, 211n34 Organized Crime Control Act of 1970, 147–56 organized crime in Chicago, 7, 74, 187n6, 187n16; armistices, 24; bookmaking operations, 43, 130; class mobility and, 199n7; concessions, 5, 16, 24, 41, 61, 65, 70, 75, 85, 97, 114, 116, 124, 153, 171; confederation model, 7, 119, 125, 187n6 (see also Jewish organized crime [confederation model]); connection to Kennedy assassination, 135–38; corporatization of crime, 89, 94, 97–98, 125; creating networks, 24, 61; demise of, 166; extortion, 43–45, 151; fusion of crime, politics, community, 52–53, 94, 97–98; gangster/politician hybrid, 125; map of areas of control, 24; payoffs “clearinghouse,” 127 (see also Connection Guys); prostitution, 27,

I NDE X

130; relationship with neighborhood, 8–9, 52–53; “Scarface” version, 6, 23– 35; sports and, 74; structure, 206n13; tentacles to other locales, 127, 135–44; torpedos, 117–18, 138–44; violence and murders, 10–11, 13–21, 15–16, 19–21, 24, 28–29, 29–30, 31– 34, 56–60, 59–60, 71–74, 73–74, 86, 87, 93, 138–44, 151. See also Capone gang; North Side Gang Organized Crime in Chicago (Lombardo), 11 Oswald, Lee Harvey, 135 Our Gang: Jewish Crime and the New York Jewish Community, 1900–1940 (Weisman), 4 Outfit, The, 7, 123–33; roles parallel to corporation in, 126–27; significance of name, 125–26; trial to bring down, 157–67. See also organized crime in Chicago

P Panveno, Sam, 38 Patrick, Charles, 113 Patrick, Jack, 114 Patrick, Leonard, 5–6, 7, 26, 66, 89, 94, 95, 98, 100, 108, 113–22, 124, 135, 178; as adolescent, 28; bank robberies, 114; bribery, 164; connection to Kennedy assassination, 135–38; conviction, 47–48; cooperation with law enforcement, 45–48, 155–56; demise of, 37–48, 149–56; extortion, 43–45, 154, 161, 189n12; family background, 113, 204n15, 206n64; before federal grand jury, 40; gambling operations, 39–40, 42, 43, 47, 161; indictment, 120; influence with police, 40; influence with politicians, 40; jail time, 114–15; job at R&K restaurant, 115; juice loans, 163; last days of, 167; legitimate businesses, 41; loan sharking, 161; murder of Cowan, 117; murder of Drury, 121–22; murder of Glick, 113, 114, 160, 164; murder of Glickman, 117, 160; murder of Kolvin, 160; murder of Krotish, 117, 160; murder of Lewis, 117; murder of Mangano, 117, 158; murder of Murphy, 117, 160; murder of Ragen, 119–20, 158; mur-

223

der of Tarsch, 19–21, 158, 160, 164; murder of Zatz, 117, 160; murder of Zuckerman, 10–11, 15–16, 116, 158, 172; murder Tarsch, 116–17; RICO and, 148–56, 158–67; testimony at Alex and Carlisi trials, 157–67; as a torpedo, 117–18, 138–44; trial as performance, 159 Patrick, Mike, 45, 47, 161, 178 patronage, 42, 67, 81, 84 Pearson, Drew, 96 Pekin Inn, 56 Petacque, Art, 18, 150 Peterson, Virgie, 70 Pierce, Ralph, 127 Polish gangs, 51–52 Polsky, Norton, 19 Portugese, Alex, 72, 178 Portugese, Harry, 33–34, 178 Portugese, Jules, 4, 7, .26–31, 169, 178; independence of, 31, 34; jewelry thief, 31; murder of, 31–34; O’Banion’s murder, 28–29; during Prohibition, 30–31; shifting allegiances, 29 Posner, Michael, 210n15 Prio, Ross, 46, 127 Prohibition, 3, 7, 23, 30, 32, 58, 82, 83, 123; end of, 26 prostitution, 27, 130 Public Enemy, 145

R race riots of 1919, 192n38 racketeering, 5, 17, 57–58 Raft, George, 24 Ragen, James, 66, 94, 95, 109, 119–20, 129, 132, 142, 160, 178, 206n64; murder of, 140 Rainone, Mario, 151–52, 154–55, 155–56, 164, 178 Raymond, George, 151 Republican party, 53, 60 Ricca, Paul, 10, 46, 64, 75, 95, 116, 119, 126–27, 149, 178 Rise and Fall of the Jewish Gangster in America, The (Fried), 4 River Forest, Illinois, 38 R&K restaurant, 14, 19, 75, 96–97, 115, 158; gambling, 115–16. See also M&E restaurant Roemer, William, 38, 127, 133, 149, 206n64

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Rogers Park (neighborhood), 8, 41, 167, 172, 189n19 Roosevelt, Franklin D., 56, 69 Roselli, Johnny, 127 Rosenberg, Frank “Lefty,” 7, 16, 78, 178 Rosenberg, Louis, 58 Rosenberg, Michael, 7, 78, 91, 178; death, 92; graft, 91–92 Rosenberg, Moe, 7, 25, 69–70, 78, 91, 94, 178; death, 92; graft, 91–92; jail time, 92; tax evasion, 92 Rosengard, Julius, 39 Rosenthal, Lefty, 44, 142, 143, 150 Ross, Barney, 49, 61, 193n48, 208n12 Roti, Fred, 166, 211n34 Rottenberg, Norman, 41, 43 Rubin, Abe, 55, 59 Ruby, Earl, 136 Ruby, Jack, 61, 135–38, 136, 208–9n13, 208n12 Rumanian Steakhouse, 171 Runyon, Damon, 49; Guys and Dolls, 162 Russo, Gus, 6 Ruth, David, 23, 32, 187n4 Ryan, Frank, 116

S Saronoff, Peter, 72 Satter, Beryl, 53 Scarface (film), 23–25, 57, 145 Scarface (novel), 23 Schoenberg, Robert, 6, 56 Schuettler, Herman, 200n23 Schwartz, “Yankee,” 60, 178 Sex, Leon, 51 Shadoian, Jack, 136 Shakman decree, 42 Shepherd, William G., 54 Shoub, Harry, 51 shtarkers, 51, 65 Siben, Emilie, 41 Siegel, Bugsy, 44, 118 Silverman, Seymour, 39 Simon, Sam, 51 Simpson, O. J. (trial), 159 Skidmore, William, 61, 64, 65, 95, 179 Small, Len, 128 Snyder, Jimmy “The Greek,” 42 South Lawndale, 52, 192n29. See also Lawndale Spencer, Ray, 151 Spilotro, Tony, 44, 127, 142, 143, 150, 179 Stanton, Danny, 66, 118

I NDE X

Stein, Joe, 171 Stevenson, Adlai, 90 stuss, 28, 188n26 St. Valentine’s Day Massacre, 8, 17, 24, 25, 29, 60, 145 Syndicate, The. See organized crime in Chicago

T Tardasch, Nathan, 20 Tarsch, Willie, 14, 19–21, 65, 96–97, 160, 171, 179; death of, 97, 98; murder of, 116–17 tax evasion, 65–66 Taylor, Robert, 145 temperance, 123 Thompson, James, 42–43 Thompson, William “Big Bill,” 7, 53, 54–55, 69, 82, 93, 179; gambling approval, 89; graft, 58; organized crime and, 93 Thrasher, Frederick, 24, 50, 52, 186n11, 192n37 Time magazine, 148 Tocco, Albert, 127 Torrio, Johnny, 5, 7, 10, 23–24, 25, 58, 60, 128, 131, 179 Tosches, Nick, 6 Touhy, Roger, 94, 128, 179 Touhy Gang, 124 Tribune Sunday Magazine, 46 Truman, Harry S, 90 Tunney, Gene, 54 Turkus, Burton, 118

U University of Chicago: sociology study, 8–9, 84 Untouchables, The (television), 207n51 Uptown (neighborhood), 50

V Vogel, Eddie, 129, 179 Vogel, Mark, 157–67

W Wagner, Jim, 155 Walcott, Jersey Joe, 54 Waller, Irle, 195n81 ward committeemen, 67 wards in Chicago, 199n10; 1st, 68, 79, 116, 125, 130–31, 155, 166; 2nd, 27, 84; 12th,

I NDE X

52, 123; 20th, 50, 54, 58, 81, 84, 92, 169; 24th, 14, 70, 71, 75, 91, 92, 93, 95, 123, 171 Warren Commission, 136–38 Washington, Harold, 43 Weiner, Max, 29 Weisman, Jenna, 4 Weiss, Hymie, 24, 82, 179 Westbrook, Wesley, 82 West Ridge (neighborhood), 41 White, John, 120 Wickersham Commission, 201n51 Wiedrich, Bob, 39, 40, 46 Wooddy, Carroll H., 84

Y Yale, Frankie, 145 Yaras, David, 7, 44, 46, 95, 98, 107, 116, 118, 120, 130, 135, 160, 171, 179, 208n12; Multiple Sports News Service, 142; murder of Zuckerman, 10, 15–16; as a torpedo, 138–44 Yaras, Leonard, 44, 150–51, 179 Yaras, Ronald, 141, 179

Z Zangara, Giuseppe, 124 Zappas, Gus, 156 Zatz, David, 160 Zimmerman, Max, 152–53 Zion, Penny, 93 Zuckerman, Benjamin “Zukie the Bookie,” 5, 6, 7, 25, 53, 61, 65, 66, 78, 89, 96, 99, 160, 169, 171, 179; as adolescent, 28; businesses, 13, 16; decline of influence, 75–76; as Democrat, 69; gambling, 69–70, 89; as middle manager, 26; murder, 10–11, 13–21, 98, 101, 172; neighborhood where murdered, 14–15; police connections, 69–70; political connections, 70–71; as precinct captain, 14, 69; relation with Eller, 85; slugging, 69; as subcontractor, 13, 16–18; violence of, 69–70, 71–74 Zuta, Jack, 95, 180, 203n36

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