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Benjamin “Bugsy” Siegel

(1905-1947)
Syndicate Leader and Victim

Benjamin “Bugsy” Siegel

In superlatives about members of organized crime Benjamin “Bugsy” Siegel certainly stands out in the most precocious category. When he was 14 years old he was running his own criminal gang and soon became a power on the Lower East Side. He teamed up with Meyer Lansky and the two formed the Bug and Meyer Mob, which handled contracts for the various bootleg gangs operating in New York and New Jersey – doing so almost a decade before Murder, Inc., was formed to handle such matters. The Bug and Meyers also kept themselves busy hijacking the booze cargoes of rival outfits. While Lansky clearly was the brains of the operation, Siegel was no flunky and stood on equal footing with him. Siegel frequently bowed to Lansky’s wishes out of a genuine affection and high regard in which he held Lansky.

Meyer Lansky

Charles “Lucky” Luciano

By the time Siegel was 21 it would have been hard for him to mention any heinous crimes he had not committed. He was guilty of hijacking, mayhem, bootlegging, narcotics trafficking, white slavery, rape, burglary, bookmaking, robbery, numbers racket, extortion and numerous murders.

Frank Costello

Joe Adonis


Gaetano “Tommy” Lucchese

Giuseppe “Joe the Boss” Masseria

Along with Lansky he hooked up with some rising Italian mobsters – Lucky Luciano, Frank Costello, Joe Adonis, Albert Anastasia, Tommy Lucchese, Vito Genovese and others – and with them would become one of the founding members of the national crime syndicate. Along the way, Siegel carried out a number of murders for the new combination to bring it to fruition. (Siegel was one of the gunmen who cut down Joe “the Boss” Masseria in a Coney Island restaurant in 1931.)

Siegel was always a man of the gun, feeling that a few homicides could clear up most any problem. And he was a “cowboy.” Years later a deputy district attorney in California explained why Siegel almost always had to lend a hand personally in mob murders: “In gangster parlance Siegel is what is known as a ‘cowboy.’ This 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.”

In the 1930s, Siegel was sent from New York to California to run the syndicate’s West Coast operations, including the lucrative racing wire to service bookmakers. The Los Angeles Mafia was bossed by Jack Dragna. Siegel soon made it clear who was in charge. Considering Siegel’s reputation for violence and the fact that he had the backing of Lansky and Luciano who, from prison, sent word to Dragna that he had best cooperate, Dragna had to accept a second fiddle role.

Jack Ignatius Dragna

Just because Siegel was a bit of a psychopath didn’t mean he wasn’t a charmer. As the saying went, he charmed the pants – and panties – off Hollywood, while at the same time he functioned as a mob killer. He was so enthused about killing, he was called “Bugsy,” but not in his presence. Face to face, he was just plain Ben. A suave, entertaining sort, Siegel hobnobbed with Hollywood celebrities, including Jean Harlow, George Raft, Clark Gable, Gary Cooper, Cary Grant, Wendy Barrie (who once announced her engagement to Bugsy and never gave up hoping) and many others, some of whom put money into his enterprises. Siegel could be at a party with his “high class friends” and then slip away for a quick murder mission with a longtime murder mate of his, Frankie Carbo (who later became the underworld’s boss of boxing). Siegel played his cowboy role in 1939 when he knocked off an errant mobster named Harry Greenberg on orders from New York.

While a busy man about Hollywood, running the mob rackets and committing murder, Siegel still had time for some truly bizarre stunts. There was the time he and one of his mistresses, Countess Dorothy diFrasso, traveled to Italy to peddle a revolutionary explosive device to Benito Mussolini. While staying on the diFrasso estate, Siegel, the wild little Jew from New York’s Lower East Side, met top Nazis Hermann Goering and Joseph Goebbels. Underworld legend has it that the Bug took an instant dislike to the pair, for personal rather than political reasons, and planned to bump them off. He only relented because of the countess’s anxious pleas. The explosive device proved a failure and Bugs and his lady returned to Hollywood where he took on the added mob chore of setting up a narcotics smuggling operation out of Mexico.

Virginia Hill

In the early 1940s Lansky had Siegel scout out Las Vegas as the possible site for a lavish gambling casino and plush hotel. At first Siegel thought the idea was loony, regarding Las Vegas as little more than a comfort station in the desert for passing travelers. However, the more Siegel looked at the possibilities the more he liked the idea, and he became the enthusiastic booster for a legal gambling paradise. He talked the syndicate into putting up a couple of million dollars to build a place, and the figure soon escalated to $6 million.

Siegel dubbed the place the Flamingo, the nickname of another Siegel mistress, Virginia Hill. At one brief time after the Flamingo opened Siegel had four of his favorite women lodged in separate plush suites. They were Virginia Hill, Countess diFrasso, and actresses Wendy Barrie and Marie McDonald. Whenever she saw Wendy, Virginia went wild and once at the Flamingo punched the English actress, nearly dislocating her jaw.

1940s Flamingo Hotel

However, woman trouble was not Bugsy’s main worry. The syndicate was upset about its $6 million. When the Flamingo first opened, it proved a financial disaster. Reportedly, the mobs from around the country demanded their money back. What really upset them was the accurate suspicion that Bugsy had been skimming off the construction funds, as well as some of the gambling revenues, and having Hill park it in Switzerland for him.

The syndicate passed the death sentence on Siegel at the famous Havana conference in December 1946. Despite his later denials, the key vote was cast by Meyer Lansky and affirmed by Luciano. Siegel knew he was in deep trouble but got what he thought was an extension of time to turn the Flamingo around. By May 1947, it was making a profit and Bugsy started to relax.

“Bugsy” Siegel Death Scene

On June 20, Bugsy was sitting in the living room of Virginia Hill’s $500,000 mansion in Beverly Hills. Virginia was in Europe at the time. Siegel was reading the Los Angeles Times when two steel-jacketed slugs from an army carbine tore through a window and smashed into his face. One crashed the bridge of his nose and drove into his left eye. The other entered his right cheek and went through the back of his neck, shattering a vertebra. Authorities later found his right eye on the dining room floor some 15 feet away from the body.

Some thought Jack Dragna, nursing his longtime hatred for Bugsy, had carried out the hit personally, but this was almost certainly not true. The most informed guess was that Frankie Carbo handled the chore on direct orders from Lansky, who doubtless grieved that such an old and dear friend had to go.

In the grim months before Siegel’s murder, construction tycoon Del Webb had expressed nervousness about his personal safety with so many menacing types around the Flamingo. In a philosophical mood, Bugsy told him not to worry. He noted he himself had carried out 12 murders, all of which had been strictly for business reasons. Webb, Bugsy said, had nothing to fear because “we only kill each other.”

That was certainly true in the Bug’s case.