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Organized crime boss, Sam Giancana climbed to the top of Chicago's underworld and became a player on the national stage through shadowy ties to the Kennedys.
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In 1959, FBI agents planted a microphone in a room at the Armory Lounge in the suburb of Forest Park, which served as Giancana's headquarters. For the next six years, they were able to eavesdrop on the workings of the Mafia and gain knowledge of many criminal activities in Chicago and around the country. Though Giancana's reign as Chicago's preeminent crime boss was already heading towards its end by the close of the 1950s,
his path in the 1960s would cross with two of America's most powerful men: Robert and John F. Kennedy.
After Angeline's death in 1954, Giancana became notorious for his flamboyant social life and frequent womanizing. He was a friend of the singer and actor Frank Sinatra, and reportedly used Sinatra as a mediator with Attorney General Robert F. Kennedy, who was alienating the Mafia with his relentless campaign against organized crime in America. (The mediation was apparently unsuccessful, as Robert Kennedy persuaded FBI Director J. Edgar Hoover to place Giancana's home in Oak Park under 24-hour surveillance in 1963.)
Giancana's numerous lovers included Phyllis McGuire, of the McGuire Sisters singing group, and Judith Campbell Exner, an actress who would link Giancana to an even more powerful man: President John F. Kennedy, with whom Exner became involved when she was still seeing Giancana.
Giancana's various ties to JFK have long been the subject of speculation. Many historians believe that ballot stuffing in Chicago (then under the control of old-school Democrat Mayor Richard Daley) helped ensure Kennedy's election in 1960. Giancana himself reportedly claimed that he had helped run a vote-stealing scam in Cook County, Illinois, a district that had been the deciding factor in Kennedy's victory. On the other hand, there are also persistent rumors of Mafia involvement in JFK's 1963 assassination, perhaps as revenge for what they saw as the ingratitude of the Kennedys in the form of RFK's crusade against organized crime.
Whatever Giancana's specific link to JFK was, the two men had a nemesis in common: Fidel Castro, whom Mob leaders hated because he had taken over Cuba, with its extensive gambling rackets. The Kennedy Administration, obviously, viewed Castro's Communist regime as a threat to national security, as evidenced by the infamous Bay of Pigs invasion in April 1961. The tie between Giancana and Kennedy would again be the subject of speculation when information later surfaced that the Mafia and the Central Intelligence Agency (CIA) had joined forces sometime in the 1960s to plot Castro's assassination.
In 1965, Giancana was put on trial for refusing to testify before a Chicago grand jury investigating organized crime. He was sentenced to one year in jail. Upon his release, Giancana traveled to Mexico, where he lived in self-imposed exile until 1974. He was extradited that year by the Mexican authorities to testify before another grand jury. He was granted immunity from federal prosecution and appeared before that jury four times, but provided little information of use.
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