Sam Giancana – JFK Ties, Mistresses, and the Outfit

Sam Giancana

While we remember dozens of notorious criminals from the
recent past, few gangsters left their mark on the 20th century like
Sam Giancana did. In his decade leading the Chicago Outfit,
Giancana did more than just run the mob’s lucrative rackets. He also formed
ties with key politicians, like the Kennedys, and allegedly worked with the CIA
to overthrow the Castro Regime. He was one of the highest profile gangsters of
the mid-20th century. In fact, many people believe that Giancana’s
near celebrity status is what eventually led to his bloody downfall.

Early Days – the 42 Gang and Climb Through the Outfit

Salvatore “Sam” Giancana was born in 1908 to Sicilian immigrants who had settled on the West Side of Chicago. Giancana’s criminal disposition became apparent at an early age. As a teen, he ran with the 42 Gang, a low-level street gang sanctioned by the Chicago Mob. He proved himself to be a competent criminal, graduating from petty theft and robbery to becoming a wheelman, or getaway driver for the mafia.  He developed a criminal record early on, having been arrested several times, and was suspected of committing murder prior to his 20th birthday as well, although he was never convicted.

Giancana’s competence as a criminal, combined with his ruthless ambition, helped him rapidly ascend through the ranks of the Chicago Outfit’s hierarchy. He took advantage of the arrest and conviction of Al Capone and his to continue establishing himself as a powerful mob figure in his own right. However, in 1939, the law finally caught up with him. He was arrested for running an illegal whiskey operation and spent the next three years in prison. He quipped to his daughters that he was going to college. After his release he made a name for himself by leading the Outfit’s takeover and consolidation of Chicago’s lucrative lottery rackets and continued his rise in Chicago.

The Golden Years

Giancana’s involvement with the lottery racket cemented his position as the preeminent figure in the Chicago Outfit, and by the mid-1950s he was running the show. Giancana expanded the Outfit’s reach far beyond the borders of Chicago, establishing casinos and hotels in far flung places like Cuba and Iran. As he expanded the mob’s business, he also established ties with many politicians to facilitate business, including Joseph Kennedy, the patriarch of the Kennedy Family. Giancana was later alleged to help Kennedy’s son, Senator John F. Kennedy, clinch the crucial Chicago vote that delivered him the presidency in 1960.

Following his wife’s death in 1954, Sam Giancana lived a very flamboyant social life as well. His social circle included celebrities like Frank Sinatra, and he was involved with a string of young, attractive women, including singer Dorothy McGuire. In the early 60s he was also involved with a woman named Judith Exner, who was allegedly President Kennedy’s mistress at the same time. Exner was alleged to pass information between the two men.

Giancana was allegedly one of the mafia men the CIA
recruited to assassinate Fidel Castro. The Mafia had lost millions they had
invested in Cuba after Castro’s revolution, and the CIA allegedly saw fellow
travelers in the Mob’s leadership. Giancana was one of the key Mob leaders the
CIA recruited to plan and execute the assassination. Although Giancana did have
some people with access to Castro, he ultimately failed to follow through with
the killing.

Decline and Death

Sam Giancana’s high profile, combined with his tendency to shut associates out of mob profits they felt they’d earned, finally proved too much for the Outfit. After he was jailed in 1965 for refusing to testify before a Congressional Committee, the Mob pushed him out of his leadership position.  After his release he moved to Mexico and established a string of successful casinos there. He ran afoul of the Outfit again however when he refused to share any of his profits with them.  Despite several meetings Giancana and his former associates were never able to resolve their differences.

Giancana returned to the United States in 1974 to testify at another Congressional Committee, this time investigating the CIA’s role in assassination attempts on Fidel Castro. On June 20, 1975, days before he was slated to provide Congressional testimony, Sam Giancana was shot to death in his Oak Park Chicago residence. One of the bullets had struck Giancana in the mouth, which police believed was a signal to other Mafiosi to refrain from providing testimony against the mob. Whether he was killed to prevent his Congressional testimony, or in retaliation for his failure to resolve his differences with the Chicago Outfit have never been determined.

A Gangster from the Golden Years of the Mob

Sam Giancana made a mark on the 20th Century. His
rise from a common street thug to the head of Chicago Outfit, and his
flirtation with the highest levels of American political power are truly
unique. However, when your power and infamy arise from being a violent
criminal, it is hard to outrun your fate. Despite his high profile and powerful
connections, Giancana nonetheless came to a violent end, shot to death in his
own home by someone he likely  knew and

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