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Review: Michael Shnayerson’s “Bugsy Siegel”

Jewish Lives

“It is a short and gripping panorama of life in 1920s-1940s America, that defining epoch of struggle and stardom, hardship and grandeur, fortune and bankruptcy—and Bugsy Siegel experienced it all.”

Peering out over the Mojave Desert, Benjamin “Bugsy” Siegel supposedly dreamt of building “the god damnedest biggest hotel and casino you ever saw.” That is the story we are familiar with, indoctrinated into us from mob romanticism and Hollywood. Siegel, the suave and womanizing Jewish gangster who killed, plundered, and stole to the height of power, prestige, and the American Dream is remembered as the mobster who built Las Vegas.

Michael Shnayerson, writing as part of Yale’s “Jewish Lives” series, is tasked with producing a biography of one of the most iconic, villainous, and seductive characters in American lore on the eve of the coming of the American Century. Shnayerson begins his book, which was released last month, by noting that “of the nearly fifty biographies that so far have constituted the Jewish Lives series, all are admirable figures. There are no bootleggers among them, no racketeers, gamblers, or murderers. Until now.” Siegel may not be an admirable figure, but he is certainly a romantic, seductive, and enticing character: a man from a bygone era, a man who seems to encapsulate the worst of the American experience but also the hope of opportunity, legitimacy, and power.

Perhaps one of the reasons we find such figures like Bugsy Siegel captivating is because he stands out. In the midst of the dull, mechanical, and rote, Siegel is a “larger-than-life figure” who embodied “excitement, sensuality, and fear.” In our current malaise against the exotic, the exciting, and the fearful, such men like Siegel still drag us to him because he was a sublime individual.

How—and why—did this poor Jewish immigrant boy become one of the enduring faces of the American mafia and its romanticization? Shnayerson, echoing Malcolm Gladwell, argues that the poverty Siegel experienced drove him to supersede his parents and his origins. Barred from a legitimate society dominated by wealthy Anglo-Saxon Protestants, Siegel and other poor immigrant children turned to crime to attain what was denied to them by the barriers of the de facto aristocracy in America.

Shnayerson does not hide the fact that Siegel was a murderer, adulterer, and womanizer. He was all those things. But, as Shnayerson writes, “Bootleggers were glamorous, with the alluring hint of a dark side. Not by chance did F. Scott Fitzgerald make Jay Gatsby a bootlegger. Nor, by chance, did he have Gatsby meet up at a speakeasy with Meyer Wolfsheim, himself a bootlegger. Wolfsheim was based on Arnold ‘The Brain’ Rothstein, to judge by Gatsby’s aside to Nick Carraway that Wolfsheim fixed the 1919 World Series. But he could just as easily have been Ben Seigel.” The comparison is apt.

American culture has long had a fascination with the dark, the sinister, and the violent. So Shnayerson takes us on a whirlwind tour of Siegel’s life, from his entry to America and early childhood in the Bronx to his marriage with Esta Siegel to an escapade through Europe with Countess Dorothy di Frasso, where he had the opportunity—so the story goes—to assassinate Hermann Göring, to his life in the mob and role in bringing it to its mature form, intoxication by Los Angeles’s Hollywood scene, and a troubled romance with Virginia Hill. Siegel’s life was glamorous and violent, and perhaps that is why we cannot help but feel a certain attraction to him.

But the story of Siegel as the mafia visionary who created Las Vegas is a story too glamorous to be true. While Hollywood may like to continue peddling the myth of Siegel and Las Vegas, Shnayerson drags the Siegel creation story back down to earth. Yet Shnayerson’s demythologization of Siegel does not abrogate the romantic misty haze that surrounds him; his story remains as glamorous and violent as Hollywood’s romanticization of it.

While it is true that Siegel eventually took control of the burgeoning Las Vegas gambling environment and oversaw the expensive construction of the infamous Flamingo Hotel and Casino, the prominence of Siegel in the ur-myth of Las Vegas is imaginatively overstated. Shnayerson does not suggest that Siegel had no hand in the creation of modern Las Vegas. On the contrary, Siegel is an essential piece of the puzzle that Las Vegas long sought to suppress. However, the Hollywood mythologization of Siegel as the sole (or partnered) visionary—often with Meyer Lansky or Moe Sedway—is a figment of our own romantic imagination.

If not Ben Siegel, who? A now-forgotten nightclub owner and partner of Siegel’s, Billy Wilkerson, was the actual man on the ground who first saw the potential of Las Vegas as a destination for the vices of returning veterans and Americans hoping to strike it rich. Wilkerson was the man with the real vision. And this vision stretched back decades as he tried, and failed, to emulate the Los Angeles environment of nightclubs, restaurants, and hot spots for high-class clients. In the deserts of the Mojave—long before Siegel, Lansky, or any other mob associate—Wilkerson got the ball rolling.

Only after Billy Wilkerson had established the groundworks for transforming this patch of the Mojave into an American equivalent of Monte Carlo did Siegel and the mafia force their way into Wilkerson’s vision. In debt, Wilkerson acquiesced to their dreams as well. It made financial sense. Plus, Wilkerson needed the help to transform Las Vegas into his dream of that American Monte Carlo.

Thus began a short and contentious partnership that quickly saw tempers flare and Siegel “take charge” and force Wilkerson out. Since Wilkerson lacked the same background story as Siegel, Wilkerson has all but been written out of the picture of Las Vegas’s creation. But Shnayerson’s book enlightens us to the real facts of Las Vegas’s origins. Siegel may have taken charge, but an unknown dreamer, debtor, and failed gambler named Billy Wilkerson really set the stage for Vegas to become Vegas.

The final years of Siegel’s life are dominated by his “ill-fated romance” with Virginia Hill and his overseeing the construction of the Flamingo and its sprawling debts. When the Flamingo launched, it was hardly the romantic castle it would become. The hotel and casino were not even finished. Due to weather, many of the high rollers Siegel begged to attend its impromptu opening were unable to make it. Debt, debt, and more debt defined the project much to the annoyance of the mafia backers, who were greatly worried about the lack of progress and continual financial losses.

Siegel’s demise, so we have been told, was a combination of mafia impatience and skimming off the top. Siegel and Virginia were supposedly stealing the mob’s money. Except, again, there is little evidence of this, even though the story is often retold in the public imagination.

Siegel’s ill-fated romance with Virginia Hill, Shnayerson suggests, was the real cause of his downfall. The two were star-crossed lovers. She was intemperate but sexy, a hothead but undeniably seductive. He was the man with a vision, the man who could not be told no, and the man who would take whatever he wanted in order to have the only thing that mattered: “class” (whether stolen or earned, it mattered not to Siegel). Their relationship often boiled over into violence. Virginia wounded Bugsy. Bugsy injured Virginia and her brother. The two were constantly at odds with each other but could not break apart from each other’s grip. Virginia even tried to commit suicide but was saved by Bugsy.

Siegel’s grisly murder has only added to his allure. We do not know who killed Bugsy Siegel. But Shnayerson has his theory, shared also by Nicholas Pileggi. Virginia Hill’s brother, Chick Hill, aggrieved and emasculated by Siegel, took revenge. Can we know for sure? No. But Shnayerson lays out a compelling case for its plausibility.

Michael Shnayerson set out to write a book to keep the memory of Bugsy Siegel alive, filled with all the horror, evil, glam, and vision that has defined Bugsy Siegel ever since his death in 1947. Bugsy Siegel is much more than a book just about Bugsy. It is a short and gripping panorama of life in 1920s-1940s America, that defining epoch of struggle and stardom, hardship and grandeur, fortune and bankruptcy—and Bugsy Siegel experienced it all. Moreover, Shnayerson helps demystify the mythology around Siegel while not making the story any less sublime than what it was. In fact, Shnayerson’s biography of Bugsy makes him even more compelling and fascinating.

Paul Krause is a teacher, writer, and classicist. He is the author of the forthcoming book The Odyssey of Love and contributed to The College Lecture Today and the forthcoming book Diseases, Disasters, and Political Theory.

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