Bugsy Siegel: Daring Murder of a Gambling Kingpin

As the old Monty Python skit goes, now for something completely different. This week’s blog features mobster Bugsy Siegel. Siegel, a stone cold killer who was largely responsible for modern Las Vegas, met a mobster’s end himself.

Bugsy Siegel, Mobster

Benjamin “Bugsy” Siegel was a product of the Williamsburg section of Brooklyn, New York. As was typical, his immigrant parents worked long. hard hours for low wages. Young Ben had an early predilection for lawbreaking. Boyhood friends included Al Capone and Meyer Lansky. His early criminal activities consisted mostly of thefts. That is, until he teamed with Moe Sedway. Siegel and Sedway set up a protection racket. They threatened to burn pushcart vendors’ merchandise unless the vendor paid them a dollar for “protection.” It didn’t take Ben long to rack up a lengthy police record.

Benjamin "Bugsy" Siegel in an April 1928 mugshot.
Benjamin “Bugsy” Siegel in an April 1928 mugshot.

Siegel founded and helped run Murder, Inc. (with Meyer Lansky) and was one of its hitmen. He also took a turn as a bootlegger but turned to gambling after prohibition ended. As a hitman, he was known for his cool nerve and skill with a gun. He also acquired the nickname “Bugsy,” which he hated. It referred to the term “bugs,” which meant “crazy” and supposedly described his often-erratic behavior.

In the late 1930s, Siegel showed up in California, partly to escape legal troubles back east. Another reason, though, was to merge the syndicate’s gambling rackets with those of local L.A. boss Jack Dragna. From prison, syndicate boss Charles “Lucky” Luciano sent word that it would be “in [Dragna’s] best interest to cooperate.” Dragna got the message.

Benjamin "Bugsy" Siege (L) with actor George Raft (R)
Benjamin “Bugsy” Siege (L) with actor George Raft (R)

While in California, Bugsy managed to make influential friends in Hollywood. He hung out with some big box-office names and became something of a celebrity himself.

Siegel’s Las Vegas Dream

In the 1940s, Las Vegas was a dusty town in the middle of a desert that happened to benefit from Nevada’s legalized gambling. In 1945, William “Billy” Wilkerson, founder of The Hollywood Reporter, had a project underway: a hotel/casino in Las Vegas. Unfortunately for Wilkerson, he ran out of money. Bugsy Siegel was there to help. Sort of.

In May 1940, Siegel decided that his “partnership” with Wilkerson needed an adjustment. The adjustment coerced Wilkerson into selling his interest to Siegel and led to Wilkerson fleeing to Paris in fear for his life. Siegel was now in the driver’s seat. He named the project after his girlfriend, Virginia Hill (nicknamed “The Flamingo” for her flaming red hair and long legs).

Bugsy envisioned a luxurious hotel/casino that would attract high rollers. But in 1946, construction materials were still difficult to obtain after World War II and costs skyrocketed. Siegel’s checks began to bounce. By 1947, the Flamingo’s costs were over $6 million (almost $73 million in 2021). And it was the mob’s money.

The Flamingo Flops

The Flamingo was finally ready to open—mostly—on December 28, 1948. Singer/comedian Jimmy Durante headlined the entertainment and Cuban bandleader Xavier Cugat provided the music. Some of Bugsy’s Hollywood friends showed up, including actors George Raft June Haver, and Sonny Tufts. But the grand opening was not a success. Bad weather kept most of the invited celebrity guests away. The casino, lounge, theater, and restaurant were ready, but the hotel was still under construction. While there was gambling in the casino, the luxury rooms that would entice people to stay and gamble were not there. And on top of that, the air conditioning broke down regularly.

The Flamingo didn't look so glamorous when it opened on December 28, 1948.
The Flamingo didn’t look so glamorous when it opened on December 28, 1948.

In its first weekend, the Flamingo lost $300,000 ($3.25 million in 2021). After two weeks, the casino’s tables were still down $275,000. The entire venture closed by the end of January 1947.

The Flamingo in the 1950s
The Flamingo in the 1950s

Called on the carpet, Siegel asked for—and got—a second chance. The Flamingo reopened on March 1, 1947, and soon began turning a profit. But the profits were too small for Siegel’s mob bosses. His time had run out.

The End of Bugsy Siegel

On the evening of June 20, 1947, Siegel sat in girlfriend Virginia Hill’s Beverly Hills home reading the Los Angeles Times. Hill had flounced off to Paris after a fight several days earlier. An associate, Allen Smiley, was with Bugsy when an unknown assailant fired a .30 caliber M1 carbine nine times through a window. Hit several times, including twice in the head, Siegel died instantly.

Benjamin "Bugsy" Siegel in the L.A. morgue
Benjamin “Bugsy” Siegel in the L.A. morgue

Who killed Bugsy Siegel? The murder is still officially unsolved. One theory has it that the syndicate “Board of Directors,” including Luciano and Lansky, authorized a contract on Siegel’s life due to his reckless spending and possible theft of mob money. Another is that Moe Sedway orchestrated a preemptive hit because Siegel had been threatening him.

The day after the murder, David Berman walked into the Flamingo with mob associates Sedway and Gus Greenbaum. There the three proceeded to take over operation of the hotel and the casino.

The Morris “Moe” Greene character in The Godfather is based on Bugsy Siegel.

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