The Notorious Life and Legacy of Benjamin “Bugsy” Siegel

The Rise of a Brooklyn Street Kid

Benjamin Siegel, born on February 28, 1906, in the poverty-stricken Williamsburg neighborhood of Brooklyn, was the son of Ashkenazi Jewish immigrants from Austria-Hungary. His parents, Max and Jennie Siegel, worked tirelessly to provide for their family, but the harsh realities of their environment offered limited opportunities. From an early age, young Benjamin sought to escape the grind of poverty by turning to the streets.

As a teenager, Siegel teamed up with Meyer Lansky, a fellow street-smart youth with a sharp mind for organization. Together, they formed the Bugs and Meyer Mob, a gang that specialized in bootlegging during Prohibition and executing hits for rival crime families. Siegel’s fearlessness and unpredictability earned him the nickname “Bugsy,” a reference to being “crazy as a bedbug.” Though he despised the moniker, it became synonymous with his legend.

“Bugsy never hesitated when danger threatened,” recalled Joseph “Doc” Stacher. “When it came to action, there was no one better.”

Murder, Inc. and the National Crime Syndicate

During the late 1920s and early 1930s, Siegel became deeply entrenched in the burgeoning National Crime Syndicate under the leadership of Charles “Lucky” Luciano. This coalition of Italian, Jewish, and Irish mobsters streamlined organized crime operations across the United States. Siegel’s role as an enforcer for the Syndicate, and later as one of the founders of Murder, Inc., cemented his reputation as a ruthless killer.

Historians credit Siegel with participating in some of the Syndicate’s most infamous hits, including the murders of Joe Masseria and Salvatore Maranzano, which marked the end of the Castellammarese War. Whether Siegel personally pulled the trigger or not, his association with these pivotal events underscored his fearsome reputation.

West Coast Expansion: A New Frontier

In 1936, with his notoriety growing and heat from law enforcement intensifying in New York, Siegel moved to California. His mission: expand the Syndicate’s operations on the West Coast. Once in Los Angeles, Siegel quickly established himself as a dominant figure in the underworld, partnering with local mob boss Jack Dragna and recruiting Mickey Cohen as his right-hand man.

Siegel’s ventures included offshore gambling ships, narcotics trafficking, and control over the region’s bookmaking operations. His influence extended to Hollywood, where he mingled with stars like George Raft, Clark Gable, and Cary Grant. Siegel’s charm, good looks, and willingness to lend money—without expecting repayment—endeared him to the Hollywood elite.

“Bugsy was different from the rest of the gangsters,” observed one contemporary. “He was charming, good-looking, and loved the Hollywood scene.”

The Flamingo: A Vision for Las Vegas

By the mid-1940s, Siegel turned his attention to Las Vegas, a sleepy desert town with legalized gambling. He envisioned transforming it into a world-class destination. His opportunity came when developer William R. Wilkerson ran out of funds for the Flamingo Hotel project. Siegel took over, securing financing from the Syndicate.

The Flamingo’s construction quickly spiraled out of control, with costs ballooning from $1.2 million to over $6 million. Siegel’s hands-on management style and extravagant spending fueled tensions with his mob financiers. Despite these setbacks, the Flamingo opened on December 26, 1946. The unfinished resort struggled initially but eventually began turning a profit in 1947.

A Violent End

On June 20, 1947, Siegel’s tumultuous life came to a brutal end. While sitting in the Beverly Hills home of his girlfriend, Virginia Hill, an unknown assailant fired through the window, striking Siegel multiple times. One bullet destroyed his left eye, a grisly detail that became a media spectacle. The murder, widely believed to be a Syndicate-ordered hit, remains unsolved.

Minutes after Siegel’s death, mob associates took control of the Flamingo, ensuring its long-term success. Siegel’s vision for Las Vegas lived on, solidifying his place in history as a controversial architect of the modern Strip.

The Legacy of Bugsy Siegel

Benjamin “Bugsy” Siegel’s life is a study in contradictions. He was a ruthless killer and a visionary entrepreneur, a gangster who mingled with Hollywood stars and a dreamer who helped transform Las Vegas. Though his violent death underscores the perils of his chosen path, his legacy endures as a reminder of the ambition, charisma, and danger that defined the American underworld.

“Bugsy was a dreamer,” said one associate. “But in the end, dreams weren’t enough to save him.”