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Bugsy Siegel — the gangster straight out of a Hollywood movie

27 March 2021

9:00 AM

27 March 2021

9:00 AM

Bugsy Siegel: The Dark Side of the American Dream Michael Shnayerson

Yale, pp.248, 18.79

Benjamin ‘Bugsy’ Siegel was about as meta-gangsterish as a real life gangster could get. Born in the slums of Manhattan’s Lower East Side in 1906, he was still a teenager when he teamed up with Meyer Lansky to become a successful bootlegger and mob enforcer. But when Mayor La Guardia came along in the early 1930s to clean up New York’s underworld, Siegel moved to California, and began dressing the way film adaptations of gangsters were supposed to. He befriended actors who played characters like him, and even filmed a couple of test scenes of himself playing a gangster who was based on a gangster like him. (The studios feared him too much to hire him. After all, who was going to shout ‘Cut!’ at Bugsy Siegel?) As if that didn’t get ontologically confusing enough, his life was eventually adapted into the great Warren Beatty vehicle Bugsy (1991), in which a gangster watches himself play a gangster while getting gunned down by gangsters..

This latest, punchiest and most compact biography of Siegel arrives in the Yale ‘Jewish Lives’ series, written by Michael Shnayerson, a longtime contributor to Vanity Fair. It is also, says the author, the first book in the series to deal with a figure who is much less than admirable. Like many young immigrants who grew up on the Lower East Side during the Depression (his father was a pants-presser in a factory), Siegel was prepared to do anything to get out and stay out — and at the time that usually meant becoming either a gangster or a night club entertainer. Bugsy Siegel didn’t sing like his fellow locals Eddie Cantor or Al Jolson, and he didn’t dance as well as his friend George Raft. So he killed people — and organised their killings. He got his notorious nickname as the result of his eye-popping tantrums — so those who knew him learnt not to call him Bugsy, or he might direct that violent temper at them.

As Malcolm Gladwell argues (through Shnayerson), men such as Bugsy weren’t ‘rebelling’ against society but rather using the only talents at their disposal in ‘an attempt to join in’; and join in Bugsy definitely did. After moving to Beverly Hills in the mid-1930s, he befriended movie stars such as Cary Grant and Phil Silvers, consorted with aspiring starlets (while keeping his wife and daughters stored away in Scarsdale), spent his days grooming at the barber’s and proudly displayed himselfpeacock-like on the sun-struck Beverly Hills boulevards in $200 suits and $25 silk shirts. He was an exercise freak, who developed the build of a gymnast, and a health nut who didn’t smoke, drank moderately and made sure to moisturise and fasten his sag-alleviating chinstrap every night before going to bed.


Meanwhile, he kept the East Coast mobsters happy by running an organisation informally known as Murder Inc., which specialised in assassinating gangsters who betrayed (or might betray) their colleagues. He was said to have murdered many victims himself (such as Dutch Schultz and Harry ‘Big Greenie’ Greenberg), but he was never convicted (partly because at least one potential witness fell out of a fifth storey window while being ‘protected’ by the cops). In the late 1930s, Murder Inc. was estimated to have killed between 600 and 1,000 people. Yet Bugsy still found time to spend a good part of every day betting on horses at Santa Anita.

As one of his colleagues noted, Bugsy was ‘what is known in gangster parlance as a cowboy — a man who is not satisfied to frame a murder but actually has to be in on the kill in person’. Which was probably the same as saying (as George Raft advised James Stewart): ‘If Benny wants you to be his friend, you be his friend.’ Good advice.

But everything changed when Bugsy met Virginia Hill, a gangster-loving girl from rural Alabama who spent her life finding her own ways to ‘join in’ with the good life. At 15, she reportedly married a wealthy young man, agreed with his family to a quick annulment and went off with the settlement to find her way into the arms of a series of criminals and their accountants. (After the first of these liaisons, she returned home with armfuls of gifts for her family in a LaSalle convertible.) Her favourite writer was Thackeray and her favourite character Becky Sharp. (‘I think I could be a good woman if I had five thousand a year.’) Several liaisons later, in the company of ‘Joe Adonis’ Doto, she met Bugsy in a club, and they remained together until his murder in 1947.

When Bugsy decided to leave his mark on the world by building the first luxury Las Vegas hotel casino, he named it the Flamingo, allegedly in honour of Virginia’s long legs. She helped him design the rooms and common spaces and stood by him through some difficult and exhilarating years. It seems that Bugsy loved his project so much that he couldn’t stop selling shares in it to his mob friends. Eventually he sold more shares (a lot more in fact) than were mathematically possible.

The Flamingo didn’t open with a bang so much as a bust; and the mobsters back home started seeing red (in more ways than one). When Bugsy was shot down in Beverly Hills after a long day of self-grooming and partying, it was hard to tell which of his many enemies had cashed in on the payback. But by this point Virginia Hill was conveniently out of town, taking her first trip to Europe. It was rumoured that her younger brother might have been the trigger man.

Shnayerson’s brief life of Bugsy is a fun, absorbing read that helps make sense of an emotionally complex gangster. And it’s just long enough to fill one of those transatlantic flights many of us are waiting to take again.

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