Boardwalk Empire Season 5: The Real Bugsy Siegel

Take a look at the story of the real Benny "Bugsy" Siegel, and see how it lines up with Boardwalk Empire season 5.

This historical Boardwalk Empire article may contain season 5 spoilers.

Hollywood always had a love-hate relationship with “Bugsy” Siegel. On the one hand, he made them a lot of money, he was a great character and he gave them a not-too-nearby playground, Las Vegas. On the other hand, Siegel went to Hollywood with the intention of shaking them down. Siegel was introduced around Tinseltown by George Raft, one of the great movie tough guys, who, according to everything I’ve ever read about him from his fellow actors, was probably the nicest guy in movies. Maybe on stage too. He saved James Cagney’s life, game Humphrey Bogart a career and introduced Hollywood to “Bugsy” Siegel.

Benny “Bugsy” Siegel is another minor character, for now, on HBO’s Boardwalk EmpireFirst Spoiler: He’ll make it to the end of the series, unless they jump ahead twenty years at a time. Siegel won’t die until June 20, 1947 and Boardwalk Empire looks to be a product of the twenties and possibly early thirties. Though (Spoiler)  Enoch Johnson, who Nucky Thompson is based on, won’t die until 1968. One thing Boardwalk Empire hasn’t mentioned about Siegel and Al Capone: The two were friends since they were kids. Capone hid out at Siegel’s aunt house when he was ducking a murder rap. On the HBO show, Siegel is played by Michael Zegen. Capone is played by Stephen Graham and Steve Buscemi stars as Nucky Thompson.

Benjamin Siegel was an associate with the Luciano family, which became the Genovese family after Charlie Lucky got deported. He was a good-looking guy with a good sense of humor. “Bugsy” was one of the guys who started Murder, Incorporated. He hated the nickname “Bugsy” and was known to go off on people if they called him that to his face. He was a celebrity, made friends with celebrities and almost married a celebrity. He would have married Virginia Hill if he could have gotten his divorce earlier, a problem Raft knew well. Siegel smoked dope and dealt it. He invented Las Vegas. He was the mob’s face on the left coast until they messed up that face by shooting out one of his eyes (a Moe Greene special), an old Sicilian message or a very lucky shot.

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Siegel was born in 1906.  He was from Williamsburg, Brooklyn but made his bones on the Lower East Side. He was a thief until he got pushcart peddlers to pony up protection money. They paid to be protected from him, otherwise he’d burn down their carts. He split that take with Moe Sedway. Siegel and Meyer Lansky met when they were teenagers and together they got the tough Jews aligned the same way the Sicilians were. They called themselves the Bugs and Meyer Gang and they included Jake Buchalter and his brother and Louis, better known as “Lepke,” probably the toughest of the tough Jews and the only mob boss ever to be fried in the electric chair. Lansky is played by Anatol Yusef on Boardwalk Empire.

Word on the street is that Bugs and Meyer met Charles “Lucky” Luciano, Lucania, whatever, when Bugsy had a problem with one of Lucky’s whores. Whatever happened, they formed an understanding and went into bootlegging. Bugsy also did the occasional hit. They hits got less occasional and he and Lepke would branch out later into that as a specialty. Siegel did wet work for Dutch Shultz and others. Later on during the early days of World War II, Siegel would offer his services to personally put a bullet in the head of Nazi brass Hermann Göring and Joseph Goebbels. For free if necessary. The only thing that stopped him was the pleas of another man’s wife, Countess Dorothy DiFrasso.(Spoiler) Siegel was one of the shooters of Joe Masseria, along with Vito Genovese, Joe Adonis and the “Lord High Executioner” Albert Anastasia to close out the Castellammarese War. Siegel was also on the crew that Meyer Lansky assembled to hit Salvatore Maranzano, along with Bo Weinberg (played by Bruce Willis in Billy Bathgate) and Red Levine (who wouldn’t kill on the Sabbath, accoridng to Tough Jews author Rich Cohen). This freed Lucky and Lansky to mold the National Syndicate from Johnny Torrio’s blueprint. On Boardwalk Empire, Vincent Piazza plays Lucky Luciano, Greg Antonacci plays Johnny Torrio and Ivo Nandi plays Joe Masseria.

Siegel was only convicted once. In Miami. On gambling and vagrancy charges, though I don’t know how he was supposed to be gambling if he was vagrant. I don’t know how the cops expected him to pay his $100 fine either, but he pulled that out of a pocket that had a lot of friends.

Siegel married his childhood sweetheart Esta Krakower on January 28, 1929. She was Whitey Krakower’s sister. Whitey was in Murder, Incorporated. Siegel should have thought that one out. They couple got divorced in 1946. Siegel died in 1947. I’m just saying.

Siegel ratted Waxey Gordon to the feds because he wasn’t paying his taxes. Waxey hired the Fabrizzo brothers from his jail cell to hit Siegel and Bugsy instead hunted them all down. Except Tony Fabrizzo, who wrote his memoirs and gave them to his mouthpiece with a long detailed account of Murder Incorporated. That didn’t stop Siegel from shooting him though. Not a good idea, as it turned out, because Siegel had to lam it out of New York. Waxey Gordon is played by Nick Sandow on Boardwalk Empire.

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[related article: 21 Real Life Gangsters Who Inspired Boardwalk Empire]

Siegel went west and made Mickey Cohen his number two. Together they got into LA crime family boss Jack Dragna’s gambling operations. Siegel then took over the numbers, set up his drug route and a bookmaking operation that netted half a million a day. Siegel took over the Screen Extras Guild and the Teamsters in LA and put the thumb on Hollywood. That didn’t stop Hollywood from partying with him. After Raft introduced him, Siegel hung out with all the big names: Clark Gable, Gary Cooper and Cary Grant. Louis B. Mayer and Jack Warner. Tony Curtis and Frank Sinatra, though the future chairman of the board probably made his own introduction. And, of course, Virginia Hill. Siegel borrowed money from actors. Then he didn’t pay them back. What were they gonna do? They were actors.

Siegel tried to sell weapons to Mussolini in 1938. In 1939, Lepke, who’d taken over Murder, Incorporated after Siegel got tan, asked Siegel to kill the rat Harry “Big Greenie” Greenberg. Siegel took his brother-in-law Whitey, as well as Frankie Carbo and Albert Tannenbaum, who confessed and fingered Siegel. Whitey was shot before the case went to trial, but Bugsy got locked up. He still ate well, got to see his personal dentist and guards brought him women. Two witnesses were killed before the Greenberg case went to trial and Siegel and Carbo were acquitted. In 1944, Siegel got busted for bookmaking, but George Raft testified on Siegel’s behalf, probably on a bet, and Siegel slid on that one too.

All that trouble from gambling gave Siegel the idea of going somewhere where he could do it legitimately. He went to the desert with his old pushcart extortion partner Moe Sedway and took over the Flamingo Hotel from William R. Wilkerson. They also got a cut from the construction of the Hoover Dam. Lansky turned the whole desert over to Siegel. At first Siegel didn’t want it. He was having too much fun in Hollywood. But Lansky could be very convincing. Siegel brought his movie friends to Vegas and supplied food, booze and gambling. He pushed out Wilkerson, all the way to Paris, and redesigned the Flamingo for the syndicate. He got burned by his own contractors, who probably learned their tricks from him, and the casino wound up costing so much that he was in a big hole by the time it opened. Most of the movie people didn’t show up for the opening, the day after Christmas in 1946. George Raft did. He couldn’t save Siegel, though. Luciano ordered Lansky to have him whacked, which he did at Virginia Hill’s house on June 20, 1947.

Benjamin Siegel wasn’t actually shot through the eye, by the way. He was shot in the head and his eye popped out of its socket. Also, Meyer Lansky’s daughter said the story about Siegel getting whacked on account of Las Vegas was just a myth. Sandi Meyer says Siegel committed a much worse offense. He told Lucky Luciano to go fuck himself. Siegel would never show up late with bagels again.

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