Bugsy Siegel

• 1. Introduction

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  Benjamin Siegel, the American mobster the world remembers as Bugsy, despised that name. It came from slang for crazy, and he told people to call him Ben or Mr. Siegel. During his murder trial in 1941, some reporters wrote that his eyes were brown. Siegel answered, "You can see for yourself that they're not brown." They were blue. He lived from 1906 to 1947, and in those forty-one years he became one of the first gangsters to be a front-page celebrity. Newspapers called him handsome and charismatic. How did a poor boy from Brooklyn end up dining with film stars and earning credit as a driving force behind the Las Vegas Strip? What did the criminal organizations around him need from him? And why did one unfinished hotel in the Nevada desert matter so much to the men who held his fate in their hands?

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• 2. Brooklyn Beginnings

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  Williamsburg, a neighborhood of Brooklyn, is where Benjamin Siegel was born on the 28th of February 1906. He was the second of five children in a poor Jewish family. His parents, Jennie and Max Siegel, had emigrated from Galicia, which then belonged to Austria-Hungary. Both worked constantly for meager wages. Siegel dropped out of school as a boy and joined a gang on Lafayette Street, on Manhattan's Lower East Side. Theft was his main activity until he met Moe Sedway. Together they ran a protection racket, threatening to burn pushcart owners' goods unless each owner handed over a dollar. By his teenage years Siegel had a long criminal record that included armed robbery, rape and murder.

  Meyer Lansky entered his life during adolescence. Lansky had a brilliant mind and had already had a run-in with Charles "Lucky" Luciano. He felt the Jewish boys of his Brooklyn neighborhood should organize the way Italian and Irish youths had. Siegel was the first person he recruited. Their crew, the Bugs and Meyer Mob, grew from illegal gambling and car theft into bootlegging in several major East Coast cities. Lansky also rented Siegel out as a hitman to other crime families. The mob handled killings for bootleg gangs in New York and New Jersey, almost a decade before Murder, Inc. existed. Its members included Abner "Longie" Zwillman, Louis "Lepke" Buchalter and Lansky's brother Jake.

  Joseph "Doc" Stacher, another member, later described Siegel to Lansky's biographers. "Bugsy never hesitated when danger threatened," Stacher told Uri Dan. "While we tried to figure out what the best move was, Bugsy was already shooting. When it came to action there was no one better. I've never known a man who had more guts." Siegel was also a boyhood friend of Al Capone. When Capone faced an arrest warrant on a murder charge, Siegel let him hide out with an aunt.

  Money arrived quickly. Siegel smoked opium in his youth and took part in the drug trade. By the age of 21 he could afford an apartment at the Waldorf Astoria Hotel and a Tudor home in Scarsdale, New York. He wore flashy clothes and threw himself into the city's night life.

  On the 28th of January 1929, he married his childhood sweetheart, Esta Krakower. They had two daughters, Millicent and Barbara. Siegel had a reputation as a womanizer, and the marriage ended in 1946. His affairs included Ketti Gallian, Marie "The Body" MacDonald, Wendy Barrie from 1942 to 1943, and Virginia Hill from 1945 to 1947.

  From the 13th to the 16th of May 1929, Lansky and Siegel represented their mob at a conference in Atlantic City, New Jersey. Luciano and the former Chicago leader Johnny Torrio hosted it at the Ritz-Carlton Hotel. Siegel declared that Jewish and Italian gangsters would stop fighting one another. Two killings in New York, two years later, would test that promise.

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• 3. Syndicate Enforcer

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  The 15th of April 1931 was the day New York mob boss Joe Masseria was shot dead on Luciano's orders. Siegel, Albert Anastasia, Vito Genovese and Joe Adonis allegedly were the four gunmen. The killing ended the Castellammarese War. On the 10th of September that year, Luciano hired four gunmen from the Bugs and Meyer Mob to kill Salvatore Maranzano in his New York office. Some sources name Siegel as one of the four. Maranzano's death secured Luciano's rise to the top of the Mafia, and it marked the start of modern American organized crime.

  Afterward, Luciano and Lansky formed the National Crime Syndicate. This loose organization of crime families from different ethnic backgrounds was meant to bring order to the underworld. The Commission, the Italian Mafia's governing body, divided territories among the families and aimed to prevent new gang wars. With his associates, Siegel formed the syndicate's enforcement wing, Murder, Inc. Once he and Lansky moved on, Buchalter and Anastasia took over its control, although Siegel kept working as a hitman. His only conviction came in Miami on the 28th of February 1932, when he was arrested for gambling and vagrancy. He paid a $100 fine out of a roll of bills.

  Waxey Gordon was an enemy with a long memory. Lansky and Siegel had given the IRS information about Gordon's tax evasion, and Gordon went to prison in 1933. From his cell, Gordon hired the Fabrizzo brothers, who broke into Siegel's heavily fortified Waldorf Astoria suite with a bomb and tried to assassinate him and Lansky. Siegel hunted the brothers down and killed them.

  Tony Fabrizzo then began writing a memoir and gave it to an attorney. One of its longest chapters was to describe the nationwide kill-for-hire squad that Siegel led. The mob learned of the plan before Tony could carry it out. Siegel checked into a hospital to build an alibi, then slipped out. With two accomplices he approached Tony's house, posed as a detective to lure him outside, and shot him.

  In 1935, Siegel helped Luciano ally with Dutch Schultz. He also killed the loan shark brothers Louis "Pretty" Amberg and Joseph Amberg. The hospital alibi, however, was starting to look questionable, and that left Siegel exposed.

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• 4. California and Hollywood

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  By 1936, Siegel's associates had warned him that his alibi was shaky and his enemies wanted him dead. He left New York for California. The Mafia assigned him to build syndicate-approved gambling rackets with Los Angeles boss Jack Dragna. Siegel recruited the gangster Mickey Cohen as his chief lieutenant. Dragna knew Siegel's reputation for violence and knew Lansky and Luciano stood behind him. Luciano, from prison, sent word that cooperating was in Dragna's best interest, and Dragna accepted a subordinate role.

  On his tax returns, Siegel claimed he earned his living from legal gambling at Santa Anita Park. In reality he took over the city's numbers racket. He used syndicate money to help set up a drug trade route from Mexico. He also organized circuits with the Chicago Outfit's wire services. By 1942, bookmaking wire operations were bringing in $500,000 a day. Four years later the Outfit took over Continental Press because of problems with Siegel. It gave its share of the racing wire to Dragna, which infuriated him. Siegel still controlled several offshore casinos and a major prostitution ring. Politicians, businessmen, attorneys, accountants and lobbyists fronted for him.

  In Hollywood, doors opened at the highest level. Siegel associated with George Raft, Clark Gable, Gary Cooper and Cary Grant, and with studio executives Louis B. Mayer and Jack L. Warner. The actress Jean Harlow was his friend and the godmother of his daughter Millicent. He bought real estate and held lavish parties at his Beverly Hills home. Young stars such as Tony Curtis, Phil Silvers and Frank Sinatra admired him.

  He also ran rackets against the studios. His plan was to take over local trade unions and stage strikes, so that studios would pay him off to get the unions back to work. He borrowed from celebrities and never repaid them, certain that none would dare ask. In his first year in Hollywood, movie stars lent him more than $400,000. He opened an illegal casino at Castillo del Lago.

  Countess Dorothy di Frasso, a socialite, was one of several prominent women in his life. Her alliance with Siegel took him to Italy in 1938. There he met the Fascist dictator Benito Mussolini and tried to sell him weapons. He also met the Nazi leaders Hermann Göring and Joseph Goebbels, whom he disliked at once. He later offered to kill them, and he held back only because the countess begged him to.

  According to Siegel's own accounts, atomite was a new explosive that detonated without sound or flash. Mussolini and the Axis powers took an interest in buying it. Mussolini advanced $40,000 so that atomite could be produced on a larger scale. In 1939, Siegel gave a demonstration for Mussolini and Nazi leaders including Göring and Goebbels. The explosive failed to detonate, and Mussolini demanded his money back.

  That same year, a very different kind of demonstration was about to put Siegel in a courtroom.

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• 5. The Greenberg Trial

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  Outside his Hollywood Hills apartment on the 22nd of November 1939, Harry "Big Greenie" Greenberg was shot dead. The killers were Siegel, Whitey Krakow, Frankie Carbo and Albert Tannenbaum. Greenberg had threatened to become a police informant, and Buchalter ordered his death. Tannenbaum later confessed and agreed to testify against Siegel, who was put on trial in September 1941.

  The proceedings became notorious for the treatment Siegel received in jail. He refused prison food, he was allowed female visitors, and he was granted leave for dental visits. Siegel loudly protested what he called stories of his privileged incarceration, insisting they were untrue or grossly exaggerated. Some reporters wrote that he had a valet in prison and that he broke down in tears on the stand.

  Press coverage also dug up his past. Newspapers began calling him "Bugsy," a name that would stay attached to him long after he was dead. Florabel Muir, a Hollywood reporter who knew him well, covered the trial, and Siegel allegedly threatened her. He warned that he had people outside who would "break your legs or drop you in a hole if I say the word."

  His lawyer was Jerry Giesler. Two state witnesses died, and no additional witnesses stepped forward. Tannenbaum's testimony was dismissed. In 1942, Siegel was acquitted for lack of evidence, although his reputation was damaged. On the 25th of May 1944, he was arrested for bookmaking. George Raft and Mack Gray testified on his behalf, and he was acquitted again in late 1944. By then his attention was shifting to the Nevada desert.

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• 6. The Flamingo

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  Southern Nevada had interested Siegel since the 1930s, when he and Sedway traveled there to look for ways to expand. They found opportunities in supplying illicit services to the crews building Boulder Dam. Lansky handed his Nevada operations to Siegel, who passed them to Sedway and went back to Hollywood.

  In California, meanwhile, Siegel was refusing to report his business to the Outfit. He announced that he was running the California syndicate himself and would repay his loans in his "own good time." The mob bosses stayed patient at first, since he had proven valuable. In 1946, Siegel saw a chance to reinvent his image and move into legitimate business through William R. Wilkerson's Flamingo Hotel. In May of that year, he decided his partnership agreement with Wilkerson had to change so that he held control.

  Siegel's plan was to supply gambling, the best liquor and food, and the biggest entertainers at reasonable prices. He believed this would draw thousands of vacationers willing to wager $50 or $100, along with high rollers. Wilkerson was coerced into selling all his stakes under threat of death, and he hid in Paris for a time. From then on, the syndicate ran the Flamingo. By October 1946 its costs had passed $4 million. Mob partners came to believe that about $1 million of the overrun had been skimmed by Siegel, by Virginia Hill, or by both.

  Local observers later said Siegel's "maniacal chest-puffing" set the pattern for generations of casino moguls. One day he boasted that he had personally killed some men. Seeing panic on the face of head contractor Del Webb, he reassured him, "Del, don't worry, we only kill each other." Others described a different side of him. He donated to the Damon Runyon Cancer Fund. His Las Vegas attorney, Lou Weiner Jr., called him "very well liked" and said he was "good to people."

  The Flamingo opened on the 26th of December 1946, even though it was unfinished. Locals came, along with film figures including Raft, June Haver, Vivian Blaine, Sonny Tufts, Brian Donlevy and Charles Coburn. Construction noise greeted them, and the lobby was draped in drop cloths. During the evening, word reached Siegel that the casino was losing money. He turned verbally abusive and threw out at least one family.

  After two weeks, the gaming tables were $275,000 in the red, and the casino briefly shut down. Siegel pushed construction forward and hired Hank Greenspun as a publicist. The Flamingo reopened on the 1st of March 1947 and began turning a profit. By then, his superiors in the Outfit had run out of patience.

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• 7. Death in Beverly Hills

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  A little before 11:00 p.m. on the 20th of June 1947, Siegel sat on a sofa reading the Los Angeles Times. His associate Allen Smiley sat beside him in the living room at 810 North Linden Drive in Beverly Hills, a mansion Siegel had leased for Virginia Hill. Also in the house were Hill's brother Chick, Chick's girlfriend, Jerry Mason and the cook, Eung S. Lee.

  An unseen gunman fired through the window with a .30 caliber M1 carbine. He stood just fourteen feet away, resting the weapon on a trellis, and shrubbery hid him from the street. Nine rounds were fired and four hit Siegel. One struck the bridge of his nose and tore out his left eye, one entered his right cheek, and two hit his chest. Other shots smashed a white marble statue of Bacchus on a grand piano. Smiley's arm was grazed, but he was otherwise unhurt.

  Florabel Muir was among the first reporters at the scene. Clark Fogg, senior forensic specialist for the Beverly Hills Police Department, concluded that there were most likely two shooters. In his view one gunman could hardly have placed such precise shots in the face, because the first impact would have turned the head. No one was ever charged, and the murder remains officially unsolved. The death certificate lists homicide, with the immediate cause given as gunshot wounds of the head.

  Several theories compete. One points to a 1946 meeting of the syndicate's "board of directors" in Havana, arranged so that Luciano, then exiled in Sicily, could attend. A contract on Siegel's life was reportedly the result, and Stacher said Lansky agreed reluctantly. The aftermath suggested coordination. Within minutes of the shooting, Gus Greenbaum, Moe Sedway and David Berman walked into the Flamingo and announced new management. Moris Rosen, a mob associate and investor, helped organize the buyout of Siegel's remaining interest.

  Another theory names Mathew "Moose" Pandza, lover of Sedway's wife Bee. She had gone to him after learning Siegel was threatening to kill her husband, whose control over his finances he resented. Ralph Natale, a former Philadelphia boss, blamed Carbo, acting for Lansky. In 1987, Eddie Cannizzaro, a former gopher for Dragna, claimed he had killed Siegel under a contract from Lansky.

  The Los Angeles Herald-Express printed a morgue photograph of Siegel's bare foot with a toe tag the next day. Although he died in Beverly Hills, photographs of his body ran in papers across the country and pushed Las Vegas into the national spotlight.

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• 8. Afterlife in Memory

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  At the Bialystoker Synagogue on New York's Lower East Side, a Yahrtzeit plaque marks Siegel's death date so mourners can say Kaddish each year. It hangs below the plaque for his father, Max, who died two months before him. At the Flamingo Las Vegas, a memorial plaque to Siegel sits between the pool and a wedding chapel.

  Fiction has handled him loosely. Moe Greene in Mario Puzo's 1969 novel The Godfather, and in the 1972 film, is often assumed to be based on Siegel. His name, however, combines those of two Lansky associates who followed Siegel in Nevada, Moe Sedway and Gus Greenbaum. That suggests a blend of several Jewish mobsters of the American West.

  The 1991 film Bugsy, a highly fictionalized biography, starred Warren Beatty in the title role. That same year, Mobsters cast Richard Grieco as Siegel and Armand Assante played him in The Marrying Man. The novelist Tim Powers imagined him as a modern Fisher King in Last Call, published in 1992. Later screen versions include Michael Zegen in the HBO series Boardwalk Empire, Edward Burns in Mob City, and David Cade in the 2021 film Lansky.

  Siegel's shadow stretches into games and music. In Fallout: New Vegas, a charismatic character named Benny is visually based on him and helps develop the game's version of the Strip. On the album All Eyez On Me, Snoop Dogg raps about dreaming of owning a fly casino like Bugsy Siegel, and doing it all legal. Star Trek: Deep Space Nine had a character call him "The man who built Las Vegas."

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