In his new book, Bugsy Siegel: The Dark Side of the American Dream, author Michael Beahan Shnayerson presents a splendid history about, arguably, the most famous Jewish gangster in history, who is indeed worth “our attention.”
In his new book, Bugsy Siegel: The Dark Side of the American Dream, author Michael Beahan Shnayerson presents a splendid history about, arguably, the most famous Jewish gangster in history, who is indeed worth “our attention.”

Bugsy Siegel: The Dark Side of the American Dream is a story of early 20th-century Jewish immigrant life in America; of bootlegging and the “Roaring Twenties;” and of dreams in Hollywood and Las Vegas.

Benjamin “Bugsy” Seigel was not a good Jewish boy. Siegel led the life of a “bootlegger, racketeer, gambler and murderer.” To paraphrase journalist James Traub, he “does not deserve our admiration; but like some other figures who have yoked their lives to deplorable causes, he nevertheless deserves our attention.” 

Mike Smith
Mike Smith
Alene and Graham Landau Archivist Chair

In his new book, Bugsy Siegel: The Dark Side of the American Dream, author Michael Beahan Shnayerson presents a splendid history about, arguably, the most famous Jewish gangster in history, who is indeed worth “our attention.” It is a story of early 20th-century Jewish immigrant life in America; of bootlegging and the “Roaring Twenties;” and of dreams in Hollywood and Las Vegas. Siegel is a fascinating product of all the above.  

Shnayerson is an American journalist and contributing editor for Vanity Fair magazine. The author of eight books and more than 75 Vanity Fair stories, his book about Siegel is published under Yale University Press’ prestigious Jewish Lives series. As Shnayerson notes, those biographies “are all of admirable figures … Until now.”

Siegel was the son of Jewish immigrants from Galicia. Max and Jennie arrived in America in 1900 amidst a wave of 1 million Jewish immigrants. Like thousands of their compatriots, they settled in New York City’s impoverished lower east side. Benjamin was born there in 1906.

Michael Beahan Shnayerson
Michael Beahan Shnayerson

Shnayerson relates Siegel’s life in three overarching eras. During the first phase, Siegel became a petty crook by age 14. Hot-tempered and fearless, he was the “toughest kid on the street;” hence, the nickname “Bugsy.” As a teenager, Siegel also became a lifelong friend and accomplice of another highly successful Jewish gangster, Meyer Lansky.

Siegel hated the nickname “Bugsy.” Only the most foolish or incredibly brave called him “Bugsy” to his face. Siegel preferred “Ben.”

A “gangster capitalist,” Siegel chose an alternative career path to rise above poverty. He made a fortune as a young bootlegger during Prohibition, quickly achieving a dream that he shared with other Jewish immigrants — prosperity and material well-being. Siegel’s ultimate goal was the attainment of “class.” He declared: “That’s the only thing that counts in life … without class and style, a man’s a bum.” 

The end of Prohibition signaled the next phase of Siegel’s career. Lansky and Siegel became partners with Jewish, Italian, Irish and other gangsters to form a national crime organization: the Syndicate.  

To expand the Syndicate’s operations, Siegel was sent to California, where he became enamored of Hollywood. Calling himself a “sportsman,” Siegel spent much of his time at local racing tracks and entertaining Hollywood’s leading actors and actresses at his mansion. For a brief time, he even fancied a career as an actor — all while doing his best to control as many illegal enterprises in California as possible. 

Although married for many years with two children — his wife and family were always well-provided for — Siegel was a womanizer. He eventually developed a long and tumultuous relationship with Virginia Hill. For a few years, Siegel was a celebrity … until he was prosecuted in a well-publicized murder trial. Eventually cleared of the crime (in which he likely participated), his glory days among the Hollywood set were over.

Siegel’s final phase was an obsession. He envisioned building a new, Monte Carlo-style luxury casino among the small “sawdust-on-the-floor” gambling houses of sleepy 1940s Las Vegas. His Flamingo Casino eventually became the first such casino in modern Las Vegas. The 1981 movie, Bugsy, visually captures this era, as well as Siegel’s California days.

Siegel did not live to see its final success. Cost overruns, chaotic project management and, worst of all, rumors that he was skimming money — a sin of high magnitude among his gangster financial supporters — led to his demise. Siegel was assassinated on June 20, 1947. The case remains unsolved, but Shnayerson provides his best guess as to the culprit.

Shnayerson has written an excellent biography, the best on Siegel to date. His research includes the extensive literature about Seigel, as well as new sources such as FBI files and his personal interviews with Siegel’s living family and acquaintances. Most important, Shnayerson thoughtfully explores the historical, cultural and Jewish context of the era that produced Benjamin Siegel. The result is a well-written, insightful narrative. It is a bona fide page-turner.  

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