Bugsy Siegel Read online

  BUGSY SIEGEL

  Bugsy Siegel

  The Dark Side of the American Dream

  MICHAEL SHNAYERSON

  Frontispiece: Benjamin “Bugsy” Siegel, mug shot, 1928. NYPD/Science Source.

  Jewish Lives® is a registered trademark of the Leon D. Black Foundation.

  Copyright © 2021 by Michael Shnayerson.

  All rights reserved.

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  Library of Congress Control Number: 2020938991

  ISBN 978-0-300-22619-5 (hardcover : alk. paper)

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  For Gayfryd

  Don’t worry, don’t worry. Look at the Astors and Vanderbilts, all those big society people. They were the worst thieves—and now look at them. It’s just a matter of time.

  —Meyer Lansky

  CONTENTS

  Prologue

  1. The Lure of the Streets

  2. Marriage and Murder

  3. Sportsman in Paradise

  4. The Masterminds of Murder Inc.

  5. Going After Big Greenie

  6. The Flamingo

  7. The Start of an Ill-Starred Romance

  8. Bugsy Takes Charge

  9. His Every Red Cent at Risk

  10. The Flamingo’s First Flight

  11. Time Runs Out

  Epilogue

  Notes

  Selected Bibliography

  Acknowledgments

  Index

  PROLOGUE

  OF THE NEARLY fifty biographies that so far have constituted the Jewish Lives series, all are of admirable figures. There are no bootleggers among them, no racketeers, gamblers, or murderers.

  Until now.

  Benjamin “Bugsy” Siegel has the dubious distinction of representing all four categories. Through the 1920s, 1930s, and most of the 1940s, he and his longtime partner in crime Meyer Lansky engaged in innumerable acts of violence. By his own account, Siegel himself killed roughly a dozen men; according to one gangster, he oversaw the contract killings of far more. Yet his brute force and reckless ambition were not just focused on crime. As World War II came to an end, Siegel saw the potential for a huge, elegant casino resort in the sands of Las Vegas, a mecca for homecoming GIs and high rollers alike. Everything was converging: cars making the drive from Los Angeles in shorter time, and with air-conditioning; planes making direct flights from thousands of miles away; a war-weary generation eager for fun, the naughtier the better. And no one knew better how to profit from the booze that coursed through casinos like blood.

  In a town of cowboy-style casinos with wagon wheels on the walls and sawdust on the floors, Siegel dared to imagine a palace more suitable to Monaco than Nevada. The Flamingo, he called it, and he imported live pink flamingoes to tone up the place. The flamingoes died, and so, not long after, did Benjamin Siegel, murdered at age forty-one in the spring of 1947. Yet a legacy remains, not only in the cornucopia of other Vegas casinos that followed, but also in the impact of gambling and entertainment on American cultural and economic life. For better or worse, the story of the Flamingo, and the criminals who built it, is a Jewish-American story, starting with a Jew who wielded influence, unlike any of the subjects covered so far in Jewish Lives, at the barrel end of a gun.

  Siegel’s story is compelling on its own. But it laces through a larger one, a generational story of eastern European Jewish immigrants in the early to mid-twentieth century who found the doors of their new world closed and so, as gangsters, pursued their own dark version of the American dream. In so doing, they created a murderously effective business model—gangster capitalism, as one expert on the period defines it—that made them as powerful as the Italian mafia with which they allied, over all the channels of organized crime that seeped through and affected American society.

  New York’s Lower East Side was, of course, where this story began: the Jewish capital of America at the turn of the century. The immigrants we associate with it were entertainers: George and Ira Gershwin, Irving Berlin, Eddie Cantor, George Burns, Yip Harburg, Zero Mostel, and so many more. Vaudeville and the Yiddish theater welcomed them, and they went on to be stars.

  Most immigrant families in this rough new milieu were forced to find other escapes from abject poverty. Jacob Riis, a crusading journalist of the period, captured a sense of the odds they were up against. “The story of inhuman packing of human swarms, of bitter poverty, of landlord greed, of sweatshop slavery, of darkness and squalor and misery, which these tenements have to tell, is equaled, I suppose, nowhere else in the civilized world.”1

  Ben Siegel was born into this environment in 1906. Like many of his peers, he left school in the seventh or eighth grade. Weeks before his violent death, he would tell his two daughters, by then teenagers, that he had had no choice: his parents needed him to help support the family.

  Children could work in a factory, as Ben’s father did, but the work was backbreaking, and dangerous, even deadly. On March 25, 1911, at the Triangle Shirtwaist factory, fire killed 146 mostly young Jewish women, trapped behind locked doors when the flames began to spread. Ben was five years old at the time, old enough to remember the horrifying news. The streets of the Lower East Side offered easier and more lucrative ways to make a living. A boy just had to be tough enough to take the risks.

  Nice Jewish boys were studious, obedient, and incapable of raising their fists. “Tough Jews,” as popular historian Rich Cohen calls the proto-gangsters in his elegiac book by that title, were scrappy, daring, and all but defined by how well they fought. And for that, they had teachers of their own.

  Youth gangs had proliferated since the early days of the immigrant story in the 1880s. They guarded their turf, repelled rivals, and instilled gang loyalty, an exhilarating bond. They also engaged in petty crime and pushed away their parents’ Jewish customs, language, and religion. “There was scarcely a Jewish home on the East Side that was free from the friction between parents and children,” noted Morris Raphael Cohen, author of Law and Order (1933) and A Dreamer’s Journey (1949). “This explosive tension made it possible for the same family to produce saints and sinners, philosophers and gunmen.”2

  Siegel and Lansky established their own gang and became friends for life. Lansky was short, homely, and cautious. Siegel was nearly five-foot-ten and dashingly handsome, with deep blue eyes, a garrulous grin, and a strong profile. He had a terrifying temper that made his face glow, and a lust for violence that alarmed even his new friend Meyer.

  To those who witnessed his fits of rage, Siegel seemed possibly mad, and so earned the nickname he loathed. Being perfectly equipped to fight on a moment’s notice may rather have been utterly sane. “If you’re in the world he grew up in, and you are characterized by muscle, then you have to play your part,” suggests writer and mob historian Nick Pileggi. “There were three jobs: muscle, brains, or the well-connected guy to politicians.” Siegel was suited to the first: “Large, tough, and unbelievably headstrong.”3 Albert Fried in The Rise and Fall of the Jewish Gangster in America gives Siegel more credit than that. “Both men were exceedingly smart and exceedingly ruthless,” Fried notes. “Their qualities o
f mind and character, not the superficialities of style and manner, accounted for the astonishing success of their joint enterprise.”4

  Soon Siegel and Lansky were consorting with an older group of gangsters. These were Jews who had graduated from petty crime to more lucrative undertakings, like racketeering. That the merchants they squeezed were fellow Jews bothered them not at all, nor that their victims spoke Yiddish as they did. The Lower East Side had winners and losers; which you were was up to you.

  Some years ago, Malcolm Gladwell in the New Yorker wrote one of his signature pieces on why immigrants turned to crime, and what happened after they did. His source was The Crooked Ladder, by sociologist James O’Kane. “The Jewish gangsters of the early twentieth century couldn’t hope for the rewards of hard work; they couldn’t conform when no one would let them try,” Gladwell related. “Yet they revered America and all it stood for.” Barred from most professions by antisemitism, they climbed, instead, the crooked ladder of social mobility. “Crime was the means by which a group of immigrants could transcend their humble origins,” Gladwell wrote, channeling O’Kane. “Criminal activity, under those circumstances, was not rebellion. It wasn’t a rejection of legitimate society. It was an attempt to join in.”5

  A brand-new way up the crooked ladder came a century ago at midnight on January 17, 1920, with the start of Prohibition.

  Within weeks, Siegel and Lansky were making midnight booze runs for Arnold “The Brain” Rothstein, grand panjandrum of gambling and fixer extraordinaire. There were no social barriers to this new criminal life of bootlegging, no minimum age. Siegel was fourteen, Lansky not quite twenty. It was a golden opportunity, a great, collective, inconceivable dream come true.

  Fortunes were made overnight, but there were costs, as rivals ambushed one another’s booze-filled trucks on late-night country roads. Most of the shoot-outs occurred along ethnic lines. By the late twenties, the gangsters began trying to end the mayhem. The turning point came in 1931, when Lansky and Siegel, along with Lucky Luciano, brought Irish, Italian, and Jewish bootleggers together to establish order in their underworld. The Syndicate, as it became known, would be American in the truest sense: an amalgam of immigrants making their way in the New World. A business in which money, not murder and revenge, would be the modus operandi. The gangsters were gangster capitalists now, engaged in the business of making a profit for all.

  With the end of Prohibition in 1933, the Syndicate, flush with bootlegged millions, slid into gambling: legal and illegal, East Coast and West. Lansky moved to Miami and focused on building a gold coast of gambling joints. Siegel went to Los Angeles to muscle in on the local lords of vice. Soon he was prospering in the lurid L.A. of Chinatown. He owned pieces of nightclubs and restaurants, dog and horse tracks, an offshore gambling ship. There was a whole other fortune to be made by the race wire: illegal off-track horse betting by telegraph. Siegel was working on that, too.

  Drawn to the ultimate trappings of wealth, Siegel built a mansion in Holmby Hills, north of Sunset Boulevard. With his movie star good looks and seemingly limitless bankroll, he entertained Jimmy Stewart, Clark Gable, Cary Grant, Charles Boyer, Fred Astaire, Marlene Dietrich, and more. The stars were dazzled, as only gangsters could dazzle them. They studied his mannerisms and thrilled to his stories. He was a gangster capitalist and a gangster celebrity: Gatsby with a penchant to kill.

  Siegel hated almost everything about the state that spanned California’s eastern border, starting with its desert heat. But by the mid-1930s he came to see the promise of Nevada as his next big act. It had legalized gambling in 1931—the only state to do so—and thousands of workers on the new Hoover Dam had flocked to Las Vegas on Friday nights, eager to blow their paychecks on games of chance. Up in Reno, gambling was held by a handful of Christian families—no Jews welcome—but Las Vegas was wide open, and just five hours by car from L.A., close enough to draw a swanky crowd. “Siegel shared his idea with Lansky, and Lansky liked it,” relates Stephen Birmingham in The Rest of Us.6 “There was no reason why they couldn’t have the southern part of the state to themselves.”

  Siegel wanted more than a few modest, moneymaking joints. He sensed the potential for a “carpet casino” more suited to Europe than the desert sands of Nevada. Others tried. But as Fried says, Siegel was the one with vision. “None of them, not even Lansky, had his audacity, his sense of the grandiose, his courage (or foolhardiness) to attempt the really big move. None had his genius.”7 And so was built the Flamingo, after its first visionary, an L.A. entrepreneur named Billy Wilkerson, took in Siegel and Lansky as investors, only to be pushed out.

  Siegel had hoped the Flamingo would let him go legit, the hope of every Jewish-American gangster. He told his backers not to worry that costs had soared, from $1 million to $6 million. He saw the fortunes about to be made. He knew what to do; they were lucky to have him. His backers weren’t used to being talked to that way. For some months after the Flamingo’s disastrous opening in December 1946, Siegel’s friendship with Lansky kept him safe—until it didn’t.

  Despite Siegel’s murder on the night of June 20, 1947, or perhaps because of it, the Flamingo took flight at last, redolent with gangster mystique. Along with twenty-four-hour gambling, it offered famous entertainers, a trend other casinos embraced. Families could stay the night in its richly appointed rooms, then play golf or ride horses by day. This was the business model: a grand destination that would grow, in time, to be the new Las Vegas and affect gambling world round. Ultimately, its ill-gotten gains would be fully absorbed by a casino industry in which the underworld and big business merged. Siegel had all but driven the Flamingo into bankruptcy. Yet his death gave it new life, luring crowds with its ambiance of anything goes: casino noir.

  Jewish gangsters built nearly all of the Vegas casinos that followed, but without Siegel’s swagger and pomp. And then, one by one, they disappeared. Settled as they now were in American society, a new generation of Jews did all they could to put their gangster days behind them. They enrolled their children in private schools and Ivy League colleges, pushing them to become lawyers and doctors. They lived in wealthy suburbs, often antisemitic ones: the push, as before, was to assimilate. “Most people have never heard of Jewish gangsters,” suggests Cohen in Tough Jews. “They do not believe they ever existed.”8

  Gone with those larger-than-life characters is a particularly vivid chapter of early-twentieth-century history in which crime and keen ambition pulled a generation up from poverty to glamour, riches, and power. The names of those upstarts echo dimly today, though Bugsy’s seems one of the most enduring, his story carried farthest from its time to the present. It resonates because Siegel was both beautiful and violent, a scintillating mix that goes through us in jolts of excitement, sensuality, and fear.

  This short biography is meant to keep Bugsy’s memory and importance alive, as a testament without judgment that a century ago, a small band of immigrant Jews did what they had to do to succeed in a harsh new world, assuring that their offspring would get to traverse the bright side of the American dream.

  1

  The Lure of the Streets

  THE STREETS WERE what struck any immigrant first—the teeming, poverty-steeped streets of New York’s Lower East Side. Max Siegel and Jennie Riechenthal, future parents of one of America’s most murderous gangsters, experienced that visceral onslaught on July 1, 1900, when they disembarked from the SS Etruria, along with the ship’s eight hundred other immigrants in steerage.1 Their time on the ocean from Liverpool, England, had been so horribly uncomfortable that they never discussed the passage with their family—not a word.2

  Max was twenty, his future wife nineteen. They came from Galicia, a poor region in the Austro-Hungarian empire, from which a steady, westward migration of desperate Jews was flowing.3 Later, family members would suggest both Max and Jennie came from the same town, not in Galicia but in Ukraine.4 Ukraine was a crown territory between Galicia and Russia, so both versions may have denoted the
same place.

  For that matter, so could Russia, the country Max Siegel identified as his homeland on the Etruria’s manifest. Many Ukrainians in the late nineteenth century identified themselves as “Little Russians,” rejecting Galicia and embracing the czarist empire. Max may have been making a political statement of solidarity, even as he recognized that America was his only hope for a new and better life. He may also have been induced to leave Galicia by recent shows of bigotry: in 1898, a priest’s antisemitic rants had led to massive damage inflicted on Jewish property, and mobs had gathered.5 On the Etruria’s manifest, Max noted that his father had paid for his passage, and that he was joining a relative on Division Street, which may or may not have been true. Basically, Max and Jennie were on their own. According to the Etruria’s manifest, Max had $15.

  Together if not yet married, Max and Jennie joined a next great wave of Jewish immigrants to America, less intent on religious reform than on escape from persecution and a chance for their children to rise. In the decade between 1900 and 1910, nearly one million immigrants a year came to America. The vast majority were from eastern Europe, and most of those were Jews.6 They made their way from the docks to the Lower East Side with their bundles of meager belongings, hoping for new lives in this American shtetl of more than one million people, four thousand residents per block, more tightly crammed than the population of Bombay, India.7

  Years later in a police interrogation, Siegel would say he was born in Brooklyn, “right around the bridge.”8 There was a case to be made for Brooklyn as the family’s first borough. Rents were even cheaper than the Lower East Side. The Williamsburg Bridge opened in 1903, making Brooklyn more accessible, especially for Orthodox Jews, who could walk on the Sabbath to and from their synagogues. Back in Galicia, Max had been a skilled tailor. In New York he got work as a presser in a pants factory, and felt lucky to have it. His salary was about $650, one census report noted, the equivalent of $17,000 today: abject poverty.9