Bugsy-SiegelBenjamin “Bugsy” Siegel (February 28, 1906 – June 20, 1947) was an American mobster with the Genovese crime family.

Siegel was often ruthless with associates and was known as one of the most “infamous and feared gangsters of his day”.

Described as handsome and charismatic, he became one of the first front-page-celebrity gangsters. He was also a driving force behind the development of the Las Vegas Strip.

Warren Beatty played Siegel in “Bugsy” (1991) a semi-fictional biography, which earned several Oscar nominations – including a Best Actor nod, for Beatty himself.

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That’s the Hollywood “fact-ion”.

Here’s some historical fact:

Bugsy’s Early Life

Benjamin Siegel was born in 1906 in Williamsburg, Brooklyn, possibly to a poor Jewish family from Letychiv, Podolia Governorate of the Russian Empire, in modern Ukraine. Other sources state that his family came from Austria.

His parents, Max and Jennie, constantly worked for meager wages. Siegel, the second of five children, vowed that he would rise above that life.

As a boy, Siegel dropped out of school and joined a gang on Lafayette Street on the Lower East Side of Manhattan. He stuck to petty theft, until he met Moe Sedway.

With Sedway, Siegel developed a protection racket where pushcart merchants were forced to pay him a dollar – or he would incinerate their merchandise.

The Bugs and Meyer Mob

During adolescence, Siegel befriended Meyer Lansky, who had formed a small mob whose activities expanded to gambling and car theft.

Lansky, who had already had a run-in with Salvatore “Lucky Luciano” Lucania, saw a need for the Jewish boys of his Brooklyn neighborhood to organize in the same manner as the Italians and Irish. The first person he recruited for this purpose was Ben Siegel.

Siegel became a bootlegger, and was involved in bootlegging within several major East Coast cities. He also worked as the mob’s hitman, whom Lansky would hire out to other crime families.

The two formed the Bugs 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.

The gang often hijacked the booze cargoes of rival outfits.

The Bugs and Meyer mob was also known to be responsible for the killing and removal of several rival gangland figures.

Siegel’s gang mates included Abner “Longie” Zwillman, Louis “Lepke” Buchalter, and Lansky’s brother, Jake.

“Doc” Stacher, another member of the Bugs and Meyer Mob, recalled to Lansky’s biographers that Siegel was fearless and saved his friends’ lives as the mob moved into bootlegging:

“ 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 to Al Capone; when there was a warrant for Capone’s arrest on a murder charge, Siegel allowed him to hide out with an aunt.

First Marriage

On January 28, 1929, Siegel married Esta Krakower, his childhood sweetheart and sister of contract killer Whitey Krakower. They had two daughters.

Siegel had a reputation as a womanizer, and the marriage ended in 1946.

A Hired Gun

By the late 1920s, Lansky and Siegel had ties to Charles “Lucky” Luciano and Frank Costello, future bosses of the Genovese crime family.

Siegel, along with Albert Anastasia, Vito Genovese, and Joe Adonis, were allegedly the four gunmen who shot New York mob boss Joe Masseria to death on Luciano’s orders on April 15, 1931. This formally ended the Castellammarese War.

On September 10 of that year, Luciano hired four trigger men from the Lansky-Siegel gang (some sources identify Siegel as one of them) to murder Salvatore Maranzano, establishing Luciano’s rise to the top of the U.S. Mafia and marking the beginning of modern American organized crime.

Murder, Inc.

In 1931, following Maranzano’s death, Luciano and Lansky formed the National Syndicate, an organization of crime families.

The Commission was established, for dividing Mafia territories and preventing future wars.

With his associates, Siegel formed Murder, Incorporated, the “enforcement” arm of the Commission.

After Siegel and Lansky moved on, control over Murder, Inc. was ceded to Lepke Buchalter and Albert “Mad Hatter” Anastasia.

Siegel continued working as a hitman. His only conviction was in Miami, where, on February 28, 1932, he was arrested for gambling and vagrancy. From a roll of bills, he paid a $100 fine.

The Fabrizzo Killings

During this period, Siegel had a disagreement with the Fabrizzo brothers, associates of Waxey Gordon.

Gordon had hired the Fabrizzo brothers from prison after Lansky and Siegel gave the IRS information about Gordon’s tax evasion. It led to Gordon’s imprisonment in 1933.

Siegel hunted down the Fabrizzos, killing them after their failed assassination attempt on Lansky and Siegel.

After the deaths of his two brothers, Tony Fabrizzo began writing a memoir and gave it to an attorney. One of the longest chapters was to be a section on the nationwide kill-for-hire squad led by Siegel.

The mob discovered Fabrizzo’s plans before he could execute it.

In 1932, Siegel checked into a hospital, and later that night sneaked out. Siegel and two accomplices approached Fabrizzo’s house and, posing as detectives to lure him outside, gunned him down.

According to hospital records, Siegel’s alibi for that night was that he had checked into the hospital.


Siegel had learned from his associates that he was in danger. His hospital alibi had become questionable, and his enemies wanted him dead.

In the late 1930s, the East Coast mob sent Siegel to California.

Since 1933, Siegel had traveled to the West Coast several times, and in California, his mission was to develop syndicate gambling rackets with Los Angeles crime family boss, Jack Dragna.

Once in Los Angeles, Siegel recruited gang boss (and personal Dragna rival) Mickey Cohen, as his chief lieutenant.

Knowing Siegel’s reputation for violence (and that he was backed by Lansky and Luciano who, from prison, sent word to Dragna that it was in his best interest to cooperate), Dragna accepted a subordinate role.

Siegel moved Esta and their daughters, Millicent and Barbara, to California.

On tax returns he claimed to earn his living through legal gambling at Santa Anita Park, near Los Angeles.

In Los Angeles, Siegel used money from the syndicate to set up a numbers racket; this helped the East Coast mob consolidate their profits. He helped establish the syndicate’s drug trade route from the U.S.A. to Mexico, and organized circuits with the Chicago Outfit’s Trans-America Wire service.

By 1942, $500,000 a day was coming from the syndicate’s bookmaking wire operations.

However, in 1947, because of problems with Siegel, the Chicago Outfit took over the Continental Press and gave the percentage of the racing wire to Jack Dragna. This infuriated Siegel.

Despite his complications with the wire services, Siegel controlled several offshore casinos and a major prostitution ring. He also maintained relationships with politicians, businessmen, attorneys, accountants, and lobbyists who fronted for him.


In Hollywood, Siegel was welcomed in the highest circles, and befriended by stars. He was known to associate with George Raft, Clark Gable, Gary Cooper and Cary Grant, as well as studio executives Louis B. Mayer and Jack Warner. Actress Jean Harlow was a friend of Siegel’s, and godmother to his daughter Millicent.

Siegel led an extravagant life; he bought real estate, and threw lavish parties at his Beverly Hills home. He gained the admiration of young celebrities, including Tony Curtis, Phil Silvers, and Frank Sinatra.

Siegel had several extra-marital relationships with actresses, including socialite Dorothy DiFrasso, the wife of an Italian count.

The alliance with the countess took Siegel to Italy in 1938, where he met Benito Mussolini (to whom Siegel was trying to sell weapons), and German Nazi leaders, Hermann Göring and Joseph Goebbels. Siegel took an instant dislike to the Nazis, and offered to kill them. He relented only because of the countess’ anxious pleas.

In Hollywood, Siegel worked with the crime syndicate to form illegal rackets.

He devised a plan to extort the movie studios. Siegel would take over local unions (the Screen Extras Guild and the Los Angeles Teamsters), and stage strikes to force studios to pay him off, so that the unions would start working again.

He borrowed money from celebrities and didn’t pay them back – knowing that they would never ask him for the money. During his first year in Hollywood, Siegel received more than $400,000 in loans from movie stars.

The Greenberg Killing

On November 22, 1939, Siegel, Whitey Krakower, Frankie Carbo, and Albert Tannenbaum killed Harry “Big Greenie” Greenberg. Greenberg had threatened to become a police informant, and Lepke Buchalter, boss of Murder, Inc., ordered his killing.

In September 1941, Siegel was tried for the Greenberg murder. Whitey Krakower was killed before he could face trial.

The trial gained notoriety because of the preferential treatment Siegel received in jail; he refused to eat prison food, and was allowed female visitors. He was also granted leave for dental visits.

Siegel hired attorney Jerry Giesler to defend him.

In 1942, Siegel and Carbo were acquitted, due to insufficient evidence and the deaths of two state witnesses, but his reputation was damaged.

During the trial, newspapers revealed Siegel’s past and referred to him as “Bugsy”. He hated the nickname (said to be based on the slang term “bugs”, or “bughouse”, meaning “crazy”, used to describe his erratic behavior), preferring to be called “Ben” or “Mr. Siegel”.

Las Vegas

Siegel wanted to be a legitimate businessman, and in 1946, he saw an opportunity, with William R. Wilkerson’s Flamingo Hotel.

Popular folklore has it that the project was named after Virginia Hill (August 26, 1916 – March 24, 1966), a Chicago Outfit courier who was Siegel’s girlfriend at the time. Nicknamed The Flamingo, she was also the former lover of Genovese family (then the Frank Costello crime family) member Joe Adonis.
Las Vegas gave Siegel his second opportunity to reinvent himself.

In the 1930s, Siegel had traveled to Southern Nevada with Meyer Lansky’s lieutenant Moe Sedway on Lansky’s orders, to explore expanding operations. There were opportunities in providing illicit services to crews constructing Hoover Dam.

Lansky had turned the desert over to Siegel. But Siegel had turned it over to Moe Sedway, and left for Hollywood.

Lansky now asked Siegel to watch over Wilkerson’s desert development. Siegel (who knew Wilkerson and lived near him in Beverly Hills) was the obvious choice as a liaison, but Siegel wanted no part in the operation that would take him back to Nevada. It meant leaving Beverly Hills and his playboy life.

But at Lansky’s insistence, Siegel consented.

In the mid-1940s then, Siegel was lining things up in Las Vegas, while his lieutenants worked on a business policy to secure all gambling in Los Angeles.

The Flamingo Hotel

Throughout the spring of 1946, Siegel proved useful. He obtained black market building materials.

At first Siegel seemed content to do things Wilkerson’s way. Under Wilkerson’s tutelage, Siegel learned the mechanics of building an enterprise.

However, Siegel began to feel intimidated and paranoid. He grew resentful of Wilkerson’s vision for the desert.

Siegel began making decisions without Wilkerson’s authority. Informing work crews that Wilkerson had put him in charge, Siegel ordered changes which conflicted with the blueprints.

The problem came to a head when Siegel demanded more involvement in the project. To keep the project moving, Wilkerson agreed that Siegel could supervise the hotel, while Wilkerson retained control of everything else.

In May 1946, Siegel decided the agreement had to be altered, to give him full control of the Flamingo.

With the Flamingo, Siegel (in his own mind) would supply the gambling, the best liquor and food, and the biggest entertainers, at reasonable prices. He believed these attractions would lure not only the high rollers, but thousands of vacationers willing to lose $50 or $100.

Siegel offered to buy out Wilkerson’s creative participation with corporate stock – an additional 5 percent ownership in the operation (Siegel later reneged).

On June 20, 1946, Siegel formed the Nevada Project Corporation of California, naming himself president. He was also the largest principal stockholder in the operation – which defined everyone else merely as shareholders.

William Wilkerson was eventually coerced into selling all stakes in the Flamingo, under the threat of death, and went into hiding in Paris for a time.

From this point the Flamingo became syndicate-run.

Trouble in the Desert

Siegel began a spending spree. He demanded the finest building that money could buy, at a time of postwar shortages.

Each bathroom in the 93-room hotel had its own sewer system (cost: $1,150,000); more toilets were ordered than needed (cost: $50,000). Because of the plumbing alterations, the boiler room was enlarged (cost: $113,000), and Siegel ordered a larger kitchen (cost: $29,000).

Adding to the budgetary over-runs were problems with dishonest contractors and disgruntled, unpaid builders.

By day, trucks delivered black-market goods. By night, the same materials were smuggled back and resold to Siegel a few days later.

As costs soared, Siegel’s checks began bouncing.

By 1947, the Flamingo cost was over $6 million ($62,500,000 in today’s money).

The first indication of trouble came in November 1946, when the syndicate issued an ultimatum: provide accounting, or forfeit funding.

Producing a balance sheet was the last thing Siegel wanted to do.

Siegel staged a private fundraising campaign, by selling nonexistent stocks.

He doubled his work force, believing the project could be completed in half the time. Siegel paid overtime.

In some cases, bonuses tied to project deadlines were offered as a way to increase productivity.

By late November, the work was nearly finished.

Under pressure for the hotel to make money, Siegel moved the grand opening from Wilkerson’s original date of March 1, 1947 to December 26, 1946, in an attempt to generate enough money from the casino to complete the project and repay investors.

However, Siegel created confusion with the opening date.

On a whim, he decided a weekend would be more likely to entice celebrities away from home. Invitations were sent out for Saturday, December 28.

Siegel changed his mind again, and invitees were notified by phone that the opening had been changed back to the 26th.

The Last Straw

Problems with the Trans-America Wire service had cleared up in Nevada and Arizona, but in California, Siegel refused to report business. He later announced to his colleagues that he was running the California syndicate by himself, and that he would return the loans he had taken out in his “own good time”.

Despite his defiance to the mob bosses, they were patient with Siegel because he had always proven to be a valuable man.

The Flamingo opened on December 26, 1946. The casino, lounge, theater, and restaurant were finished.

Although locals attended the opening, few celebrities materialized. A handful drove in from Los Angeles despite bad weather. Among those present were June Haver, Vivian Blaine, George Raft, Sonny Tufts, Brian Donlevy, and Charles Coburn.

They were welcomed by construction noise, and a lobby draped with drop cloths. The desert’s first air conditioning system collapsed regularly.

While gambling tables were operating, the luxury rooms that would have served as the lure for people to stay and gamble, were not ready.

As word of the losses made their way to Siegel during the evening, he began to rant and rave, throwing out at least one family.

After two weeks, the Flamingo’s gaming tables were $275,000 in the red, and the entire operation shut down in late January 1947.

After being granted a second chance by the Commission, Siegel cracked down and did everything possible to turn the Flamingo into a success by making renovations and obtaining good press. He hired future newsman Hank Greenspun as a publicist.

The hotel reopened on March 1, 1947 – with Meyer Lansky present – and began turning a profit.

However, by the time profits began improving, the mob bosses above Siegel were tired of waiting.

The Death of Bugsy Siegel

On the night of June 20, 1947, as Siegel sat with his associate Allen Smiley in Virginia Hill’s Beverly Hills home reading the Los Angeles Times, an assailant fired at him through the window with a .30-caliber military M1 carbine, hitting him many times – including twice in the head.

No one was charged with the murder, and the crime remains officially unsolved.

A probable cause of Siegel’s death was his excessive spending (and possibly stealing) of money from the mob.

In 1946, a meeting was held with the “board of directors” of the syndicate in Havana, Cuba; a contract on Siegel’s life was the conclusion.

The day after Siegel’s death, the Los Angeles Herald-Express carried a photograph on its front page from the morgue, of Siegel’s bare right foot with a toe tag.

Although Siegel’s murder occurred in Beverly Hills, his death thrust Las Vegas into the national spotlight, as photographs of his lifeless body were published in newspapers throughout the country.

The day after Siegel’s murder, David Berman and his Las Vegas mob associates walked into the Flamingo and took over operation of the hotel and casino.

In the Bialystoker Synagogue on Manhattan’s Lower East Side, Siegel is memorialized by a Yahrtzeit (remembrance) plaque that marks his death date, so that mourners can say Kaddish for the anniversary. Siegel’s plaque is below Max Siegel’s, his father, who died two months before his son.

On the property at the Flamingo Las Vegas, between the pool and a wedding chapel, is a memorial plaque to Siegel.

Siegel is interred in the Hollywood Forever Cemetery in Hollywood, California.

And that’s the end – of this one.

See you, for our next story, I hope.

Till then.