Sam Giancana Biography

Sam Giancana, an American organized-crime boss of Sicilian descent, was a prominent figure in the Chicago underworld during the 1950s. Known for his ties with influential politicians like the Kennedys, Giancana’s rise to power began in his youth when he joined the notorious ’42 Gang’ and engaged in various criminal activities. His involvement with the ‘Chicago Outfit’ as a getaway driver propelled him to higher ranks within the underworld due to his ruthless and vicious nature. Giancana’s influence extended to Chicago’s lottery rackets, which he took over by eliminating his rivals in cold blood. However, his association with the mob and alleged involvement in helping Kennedy win the presidential elections would later lead to his downfall when Kennedy’s brother pursued the mafia. Giancana’s connection with the ‘Central Intelligence Agency’ (CIA) in planning Fidel Castro’s assassination, which ultimately failed, further complicated his situation. Eventually, Giancana was ousted from his position within the ‘Outfit’ and sought refuge in Mexico before returning to his Illinois home, where he met his tragic end. Married to Angelina and father to three daughters, Giancana’s life was marked by a tumultuous journey through the criminal underworld.

Quick Facts

  • Also Known As: Gilormo Giangana, Salvatore Mooney Giancana
  • Died At Age: 67
  • Family: Spouse/Ex-: Angelina DeTolve
  • Born Country: United States
  • Gangsters
  • American Men
  • Died on: June 19, 1975
  • Place of death: Oak Park, Illinois, United States

Childhood & Early Life

Giancana was born on May 24, 1908, in the West side of Chicago, to Sicilian immigrant parents. However, according to his preference, his birthdate was often mentioned as June 15. He grew up in a part of Chicago known as ‘The Patch,’ which was mostly inhabited by immigrants who had moved from ‘Little Sicily’ on Sedgwick Street.

Giancana’s mother died when he was young. His father, Antonino Giangana, had a pushcart and later owned a shop selling Italian ice. His father would often get tough while managing his son, as Sam was an uncontrollable youngster. The harsh punishments of childhood were probably responsible for Giancana’s ruthless nature.

Giancana went to ‘Reese Elementary School’ but was expelled at 10. He was then sent to ‘St. Charles Reformatory.’ However, this did not help change his behavior. He had a sister named Lena. He also had half-siblings, from his father’s other marriage.

Criminal Activities

In 1921, he became a part of the ‘42 Gang,’ or the ‘42s,’ a youth gang infamous for violence. The ‘42s’ were involved in robbing wealthy people, stealing car parts, and bootlegging. The gang worked for Joseph Esposito, the politician known for extortion, prostitution, and bootlegging. Thus they soon became part of the ‘Chicago Outfit.’

Giancana became the wheelman for the ‘Outfit’s top bosses, including Al Capone, Paul Ricca, and Tony Accardo. He was an expert getaway driver and a ruthless killer. He was first arrested at 17 (1925) for car theft. Later, he became the triggerman, or a vicious killer, of the ‘Outfit.’ By the time he turned 20, the police suspected that he was involved in three murders. However, he was not convicted.

In 1926, Giancana was charged with murder, but a key witness of the case suddenly died or was murdered. Thus, the case against him was dropped. During World War II, he was declared unfit for military service, as the ‘Selective Service’ psychologist reported him as a “constitutional psychopath.” Giancana took advantage of the war situation by manufacturing fake ration stamps and selling them at a high price.

During the late 1930s, Giancana moved away from the ‘42s’ and into the ‘Chicago Outfit.’ In 1945, he was put in the ‘Federal Correctional Complex’ in Indiana, where he learnt about Chicago’s illegal lottery rackets from a fellow inmate named Eddie Jones. After his release, he took Tony Accardo’s help to capture Chicago’s lottery rackets, also known as the ‘Policy Rackets.’ He used ruthless means and did not hesitate to murder his rivals. He abducted Eddie Jones, who had taught him about the lottery business. Following this, he eliminated Teddy Roe, another big boss of the ‘Policy’ racket.

Giancana was involved in many illicit businesses, including illegal gambling and liquor distribution. He was also in touch with several politicians. His various rackets, especially the lottery pay system, brought in a lot of money for the ‘Outfit.’ Thus, when one of the top bosses, Tony Accardo, retired from the ‘Outfit’ in 1957, Giancana took his place as the new boss.

Connections with the Kennedys and CIA

In 1957, Giancana attended the national summit of organized crime groups in Apalachin, New York, on behalf of the ‘Outfit.’ Joseph Kennedy (father of John F. Kennedy) was known to Giancana, as he was also believed to be involved in bootlegging. Reportedly, Giancana was asked to help in J.F. Kennedy’s 1960 presidential campaign, which he did successfully.

Later, President Kennedy appointed his brother, Robert Kennedy, as an attorney general, who began taking action against the mobsters, especially the ‘Outfit.’ Around this time, the ‘CIA’ reportedly contacted Giancana and some other mobsters in connection with a plan to assassinate the Cuban prime minister, Fidel Castro.

During this period, Giancana had a girlfriend named Judith Exner, who was also a mistress of J.F. Kennedy. Allegedly, there were other popular personalities, such as singer Phyllis McGuire and actor Marilyn Monroe, who were known to both the politician and the mobster. Exner often carried secret communications between the two, which were supposed to be about the plan to assassinate Castro. Reportedly, she was Kennedy’s connection with the organized crime arena.

Giancana was offered a huge amount by the ‘CIA’ to assassinate Castro. However, he and his other associates, such as Roselli and Trafficante, refused to accept the money, stating that they would do the job as their patriotic duty. The three planned and made repeated attempts to assassinate Castro but failed each time.

Decline and Assassination

In 1963, J.F. Kennedy was assassinated, and many suspected the involvement of the ‘Outfit.’ However, nothing was proved. It was assumed that Robert Kennedy’s action against the mob was the reason behind the ‘Outfit’s involvement in the assassination.

The ‘Chicago Outfit’ was not very happy with Giancana, especially because of the ‘FBI’ attention he was attracting (with his involvement with the ‘CIA’s plans). Similarly, he did not share the profits he earned from his casinos in Iran and Central America. This caused immense displeasure in the ‘Outfit.’

In 1965, Giancana was called to testify (about organized crime) before the grand jury. As he was told not to speak, he maintained the silence characteristic of the mafia and refused to testify. Thus, he had to serve a 1-year term. During this period, he was replaced as the ‘Outfit’s boss. After his prison term, he moved to Mexico (Cuernavaca). Reportedly, the Mexican government deported him back to the U.S., and he returned in July 1974.

The ‘U.S. Senate’ select committee (the ‘Church Committee’) called him and Roselli for a hearing on the role of the ‘CIA’ and the underworld in the attempted assassination of Castro. However, before he could testify, on June 19, 1975, Giancana was shot from behind in the basement kitchen of his Oak Park house in Illinois. The case remained unsolved.

Family & Personal Life

On September 23, 1933, Giancana married Angelina DeTolve. Angelina’s parents were Italian immigrants. The couple had three daughters, Bonnie, Francine, and Antoinette. His wife died in 1954, after which he reportedly had several affairs.

Giancana played a major role in the 1965 movie ‘Peep Show.’ He was also depicted in several movies and TV series. A book on his life, ‘Double Cross: The Explosive, Inside Story of the Mobster Who Controlled America,’ was published by his half-brother and nephew.

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