This article is taken from the July 2021 issue of The Critic. To get the full magazine why not subscribe? Right now we’re offering five issue for just £10.

---

In a letter to the United States’ Draft Board in 1944, “Bugsy” Siegel described himself as “an investment broker” with an annual income of $50,000. “I consider various propositions concerning investments in enterprises, and if satisfactory, enter in to such deals … I usually obtain an interest in return for my work. I’m required to make trips to appraise and investigate all matters connected with enterprises, and to negotiate terms.”

He may have sounded like a banker, but Siegel was one of America’s most notorious gangsters. Yale University’s highly regarded “Jewish Lives” series of short biographies includes such varied subjects as Karl Marx and Irving Berlin, but this is the first title devoted to a murderous scoundrel.

There is no doubt that Nick Berish Bennie “Bugsy” Siegel was also handsome, charming, intelligent, and glamorous, but quite apart from being a fascinating biographical subject, he is able to stand proxy for a strain of Jewish American life that, for a period, gloried in gangsterism.

Poor Jewish boys from New York, with little prospect of becoming nice doctors or dentists, let alone investment bankers, found a niche they could understand in the booze and gambling rackets. At the same time, Siegel’s younger brother, Maurice, his education subsidised by Siegel’s illicit earnings, would become a Beverly Hills doctor.

Siegel made his first fortune as a teenage bootlegger alongside his friend Meyer Lansky by allying with Italian mobsters. Schnayerson, whose prose crackles with energy, reminds us that F. Scott Fitzgerald made Gatsby a bootlegger. Similarly, Schnayerson writes, Siegel “was a gangster capitalist and a gangster celebrity: Gatsby with a penchant to kill.”

He was also a dandy and later wore a chinstrap at night to preserve his looks. In the late 1930s, Siegel and Lansky professionalised killing by forming Murder, Inc., the Syndicate’s enforcement arm. A professional killer would be recruited from out-of-state to dispatch a Syndicate enemy; the next day he would vanish like a wisp of smoke, leaving the cops baffled.

Yet for all the brilliance of this concept, Siegel was a loose cannon. As one assassin, Allie “Tick Tock” Tannenbaum, revealed in court testimony in 1941, Siegel was “what is known in gangster parlance as a cowboy, which is the way the boys have of describing a man who is not satisfied to frame a murder, but actually has to be in on the kill in person”. He was convicted of a single killing. Siegel was fearless, a chaye (beast). He had an explosive temper and exhibited no remorse. He was also said to puncture a victim’s body to let internal gases escape before dumping it.

If one were to compile a c.v. for Siegel’s business career, it would focus on four elements: Prohibition, Murder, Inc., the race wire service which reported the results of horse races and Las Vegas. Hollywood was a sideshow for Siegel. George Raft, another childhood friend, gladly smoothed his path, Jean Harlow became godmother to his daughters, Frank Sinatra and Phil Silvers fawned over him, whereas Jimmy Stewart shunned him.

Schnayerson, whose prose crackles with energy, reminds us that F. Scott Fitzgerald made Gatsby a bootlegger

In Las Vegas, he saw the opportunity for the Syndicate to invest in a fledgling resort city based on legal gambling and celebrity. As he became consumed by his grandiose vision for his casino-hotel, the Flamingo, Siegel’s behaviour was increasingly erratic, his violence more pronounced.

Was he just an out-of-control spendthrift or was he embezzling from his gangster friends? Either way, the Syndicate gave the order for him to be rubbed out, with his buddy Meyer Lansky acquiescing.

On June 20, 1947, Siegel was sitting on a sofa in the living room of his girlfriend Virginia Hill’s house with his back to the window when two high-velocity rifle bullets smashed into his neck and skull. He died instantaneously as one of his eyeballs was propelled across the room. The Syndicate looked after his family.

At the heart of this book is the dance between danger and an immigrant’s yearning for respectability. Given Siegel’s moral shortcomings, Schnayerson characterises as “downright bizarre” his scrawled 1946 memo to his wife about their teenage daughter Millicent’s “misdeeds”: dyeing her hair, smoking too much, and staying out too late (the framed letter is mounted on the wall of a Las Vegas casino to this day).

One of Siegel’s two daughters ran away while the other married a Syndicate figure. Her wedding at New York’s Waldorf Astoria was paid for by Meyer Lansky. Schnayerson describes a photo of the bride thus: “Behind her walks a ghostlike Meyer Lansky. From his pained expression one can easily imagine that he had something to do with the death of his childhood friend and is trying to atone by marching that friend’s daughter up the aisle.”