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Who Was Sam Giancana?
Sam Giancana, originally named Gilormo Giancana, rose from humble beginnings to become a prominent figure in Chicago’s organized crime scene. His early career began as a wheelman for the infamous Al Capone, and he ultimately ascended to control the city’s illegal gambling operations. Giancana’s extensive connections with influential politicians, including members of the Kennedy family, positioned him as a significant player in both the underworld and political arenas. Notably, he was called to testify about Mafia involvement in a CIA plot to assassinate Fidel Castro, but he was murdered before he could provide his testimony.
Early Life
Sam Giancana was born on June 15, 1908 (though some sources cite May 24), in Chicago, Illinois. Baptized as Momo Salvatore Giancana, he was raised in a challenging environment on the West Side of Chicago, as the son of Sicilian immigrants. In his teenage years, Giancana led a street gang known as “The 42s,” performing minor tasks for the powerful Chicago Mafia of the 1920s, which was dominated by the notorious gangster Al Capone. He began his criminal career as a “wheelman” or driver for Capone’s organization and faced his first arrest in 1925 for auto theft. Giancana quickly progressed to the role of “triggerman” and, by the age of 20, had become a key figure in three murder investigations, though he was never tried.
Family Life
In 1933, Giancana married Angeline DeTolve, and the couple welcomed three daughters. Their daughter Antoinette later published a memoir titled Mafia Princess in 1984, shedding light on her father’s life and the family’s experiences. Throughout the 1930s, Giancana continued to rise within the ranks of organized crime, especially after the incarceration of Al Capone in 1931 (who would die in 1947). Giancana’s criminal activities led him to serve his first prison sentence in 1939 for illegal whiskey manufacturing. Following his release in the early 1940s, he set out to dominate Chicago’s illegal lottery gambling operations, particularly in the city’s predominantly African-American neighborhoods. Through a campaign of violence that included beatings, kidnappings, and murder, Giancana and his associates seized control of the numbers racket, significantly increasing the Chicago Mob’s annual income by millions of dollars.
Giancana: The Mob Boss
A psychologist who evaluated Sam Giancana during his Selective Service physical examination in World War II classified him as a “constitutional psychopath” exhibiting “strong antisocial trends.” Consequently, Giancana received a 4-F status, disqualifying him from military service. While others served, he capitalized on wartime opportunities by amassing wealth through the production of counterfeit ration stamps. By the war’s end, the Giancana family had relocated from the city to an affluent residence in Oak Park, a suburb of Chicago.
In the mid-1950s, following Anthony “Tough Tony” Accardo’s retirement as the head of the Chicago Outfit—the city’s Mafia organization—Giancana ascended to leadership. By 1955, he had gained control over gambling, prostitution, narcotics trafficking, and other illegal enterprises in Chicago. Under his command, the Chicago Mafia transitioned from a small-scale operation to a significant criminal entity. Giancana later boasted to an FBI agent that he had influence not only over Chicago but also Miami and Los Angeles.
In 1959, FBI agents installed a listening device in the Armory Lounge, Giancana’s base of operations in Forest Park. For the next six years, they monitored the Mafia’s inner workings, gaining insights into various criminal activities throughout Chicago and beyond. Although Giancana’s dominance as Chicago’s leading crime figure was waning by the late 1950s, his trajectory intersected with two of America’s most influential political figures: Robert and John F. Kennedy.
Relationship with the Kennedys
Following the death of his partner Angeline in 1954, Giancana became infamous for his extravagant social life and numerous romantic entanglements. He befriended Frank Sinatra, reportedly leveraging this relationship to engage with Attorney General Robert F. Kennedy. However, these efforts proved ineffective, as Robert Kennedy persuaded FBI Director J. Edgar Hoover to place Giancana’s Oak Park home under 24-hour surveillance in 1963.
Among Giancana’s notable liaisons were Phyllis McGuire of the McGuire Sisters and Judith Campbell Exner, an actress who would further link him to President John F. Kennedy. Speculation surrounding Giancana’s connections to JFK has persisted over the years. Many historians assert that the election’s outcome in 1960 was influenced by ballot manipulation in Chicago, under the control of the veteran Democratic Mayor Richard Daley. Giancana allegedly claimed involvement in orchestrating vote fraud in Cook County, pivotal to Kennedy’s success. Conversely, rumors of Mafia connections to JFK’s assassination in 1963 circulate, seen by some as retaliation for perceived betrayal, particularly due to Robert Kennedy’s aggressive stance against organized crime.
Regardless of the precise nature of Giancana’s relationship with JFK, both men shared a mutual adversary in Fidel Castro. Giancana and other Mafia leaders detested Castro for his takeover of Cuba, which disrupted their gambling interests. The Kennedy Administration viewed Castro’s regime as a national security threat, as highlighted by the Bay of Pigs invasion in April 1961. Speculation regarding the ties between Giancana and the Kennedys intensified when revelations emerged about potential collaboration between the Mafia and the CIA to assassinate Castro.
Imprisonment and Death
In 1965, Giancana faced trial for refusing to testify before a Chicago grand jury investigating organized crime, resulting in a one-year jail sentence. Upon his release, he fled to Mexico, where he remained in self-imposed exile until 1974. That year, Mexican authorities extradited him to testify before another grand jury. Although granted immunity from federal prosecution, his testimony yielded little valuable information.
Giancana was later summoned to testify before a U.S. Senate committee probing Mafia involvement in a failed CIA plot to kill Castro. However, prior to his scheduled appearance, he underwent gallbladder surgery in Houston, Texas. He returned to his Oak Park residence on June 17, 1975. Two days later, Giancana was shot in the back of the head and multiple times in the chin with a .22-caliber pistol while cooking in his basement. Numerous theories regarding his assassination emerged—rival mobsters, CIA agents concerned about his testimony, or one of his former lovers—but no arrests were made.
Cinematic Depictions of Sam Giancana
Giancana’s life and legacy have inspired various films, including Sugartime (1995), featuring John Turturro as the mobster, and Power and Beauty (2002). The thriller King Kennedy (2012) also showcases archival footage of Giancana, illustrating his enduring influence in popular culture.