Sam Giancana
Chicago Outfit boss with alleged CIA and political ties.
Salvatore "Mooney" Giancana (born Gilormo Giangana) was the boss of the Chicago Outfit from 1957 to 1966. He was born in Chicago’s Patch neighborhood to Sicilian immigrants. As a teen, he joined the 42 Gang, a street crew tied to political boss Joseph Esposito. Giancana earned a reputation as a skilled getaway driver, a top earner, and a violent enforcer. After Esposito was murdered—an act Giancana may have been involved in—the 42 Gang became an arm of the Chicago Outfit, led by men like Frank Nitti, Paul Ricca, and Tony Accardo. His first arrest came in 1925 for auto theft. By age 20, he was the prime suspect in three murder cases but never tried. In 1929, he was convicted of burglary and larceny and served nearly four years in Joliet Correctional Center.
In the late 1930s, Giancana became the first 42 Gang member to join the Chicago Outfit. From the early 1940s through the 1950s, he ran illegal gambling, liquor distribution, and political rackets in Louisiana through his friend H. A. Killian, who had ties to New Orleans crime boss Carlos Marcello. In 1939, Giancana was convicted of bootlegging and spent four years in federal prison. After his release in 1942, he pushed Accardo to let him take over Chicago’s black lottery payout system for the Outfit. Giancana’s crew forced Eddie Jones out of the country and murdered gambling boss Theodore Roe in 1952 after Roe killed a Giancana associate. Another Outfit member, Jackie Cerone, scared “Big Jim” Martin to Mexico with two nonfatal gunshots. The takeover brought in millions yearly and helped make Giancana the Outfit’s new boss in 1957. Still, Accardo and Ricca kept real power, and Giancana had to consult them on major decisions.
Giancana attended the 1957 Apalachin meeting in New York. When police raided it, he stayed inside the house and avoided arrest. He later claimed on a wiretap that Chicago was the safest place for a mob meeting because he had police chiefs on his payroll. Associate Hyman Larner helped expand Outfit gambling and smuggling to Panama and Iran, working with the CIA. By 1966, this partnership included arms smuggling for Israeli Mossad via Panama. Corrupt ex-cop Richard Cain served as Giancana’s courier and financial adviser, making frequent trips to Mexico.
Some sources say Giancana and the Mafia helped John F. Kennedy win the 1960 presidential election. In the 1960s, the CIA recruited him to plot the assassination of Fidel Castro. In 1965, he was convicted of contempt of court and served a year in prison. After release, he fled to Cuernavaca, Mexico, but was deported in 1974 and returned to Chicago. On June 19, 1975, Giancana was murdered at his home in Oak Park, Illinois, just before he was to testify before the Church Committee.
- born
- May 24, 1908, Chicago, Illinois
- died
- June 19, 1975, Oak Park, Illinois
- field
- Organized crime
- nationality
- American
- known_for
- Boss of the Chicago Outfit; alleged involvement in 1960 election and CIA Castro
Verified Timeline
Lore & Background
Giancana was born Gilormo Giangana on May 24, 1908, in The Patch neighborhood of Chicago to Antonio Giangana and Antonia DeSimmona, Italian immigrants from Castelvetrano, Sicily. He joined the 42 Gang, a juvenile street crew working for political boss Joseph Esposito. Giancana soon developed a reputation as an excellent getaway driver, a high earner, and a vicious killer. He was first arrested in 1925 for auto theft. By the age of 20 he had been the prime subject of three murder investigations but never tried for any of them. In 1929, Giancana was convicted of burglary and larceny, and sentenced to one to five years in the Joliet Correctional Center. He was released in 1932 after serving three years and nine months. During the late 1930s, Giancana became the first 42er to join the Chicago Outfit. In 1939, Giancana was convicted of bootlegging and sentenced to four years in Leavenworth Prison and Terre Haute Federal Correctional Complex. After his release in 1942, he convinced Accardo, then the Outfit's underboss, to stage a takeover of Chicago's African American "policy" (lottery) payout system. Giancana's crew was responsible for the August 4, 1952, murder of African American gambling boss Theodore Roe. When the lottery money started rolling in, the amount produced for the Outfit was in the millions of dollars a year, bringing Giancana further notice. He was present at the Mafia's 1957 Apalachin meeting; he avoided arrest by staying inside the meeting house. Giancana claimed the Chicago area was "the safest place in the world" for a major underworld meeting because he had several police chiefs on his payroll.
Reader's Guide
Giancana's significance lies in his leadership of the Chicago Outfit during a period of expansion and national attention. According to some sources, he and the Mafia were involved in John F. Kennedy's victory in the 1960 presidential election. Giancana's mistress Judith Exner stated that Giancana used his connections to persuade unions to support Kennedy. However, it is alleged that Giancana came to regret aiding Kennedy get elected due to the fact that attorney general Robert F. Kennedy made significant efforts to crack down on organized crime. During the 1960s, the CIA recruited Giancana and other mobsters to assassinate Fidel Castro. Giancana reportedly said that the CIA and Cosa Nostra were "different sides of the same coin." CIA documents released in 2007 confirmed that in September 1960, the CIA recruited ex-FBI agent Robert Maheu to meet with Johnny Roselli. Maheu offered $150,000 to have Castro killed, but Roselli refused any pay. Roselli introduced Maheu to "Sam Gold" (Giancana) and "Joe" (Santo Trafficante Jr.). Giancana suggested using poison pills to dose Castro's food and drink. The CIA gave these pills to Giancana's nominee, Juan Orta. In 1965, Giancana was convicted of contempt of court, serving one year in prison. After his release, he fled to Cuernavaca, Mexico. In 1974, he was deported to the United States, returning to Chicago. Giancana was murdered on June 19, 1975, at his home in Oak Park, Illinois, shortly before he was scheduled to appear before the Church Committee.
Did You Know?
- Giancana was born Gilormo Giangana on May 24, 1908, in The Patch neighborhood of Chicago.
- He was first arrested in 1925 for auto theft and by age 20 had been the prime subject of three murder investigations but never tried for any of them.
- Giancana was present at the Mafia's 1957 Apalachin meeting and avoided arrest by staying inside the meeting house.
- In 1959, Giancana appeared before the Select Committee on Improper Activities in Labor and Management, where Chief Counsel Bobby Kennedy chided him, saying 'I thought only little girls giggled, Mr. Giancana.'
- Giancana was murdered on June 19, 1975, at his home in Oak Park, Illinois, shortly before he was scheduled to appear before the Church Committee.
Frequently Asked Questions
Who is Sam Giancana?
Salvatore 'Mooney' Giancana was a Chicago-born mobster of Italian immigrant descent who led the Chicago Outfit from 1957 through 1966. He built his criminal empire through illegal gambling, bootleg liquor distribution, and political corruption.
What was Sam Giancana's role in organized crime?
Giancana served as the top boss of the Chicago Outfit, one of the most powerful criminal syndicates in the United States. Under his leadership, the organization dominated rackets in gambling, liquor, and political influence across the Midwest.
What is Sam Giancana's alleged connection to the CIA and Fidel Castro?
Giancana is frequently cited in conspiracy discussions for supposedly participating in a CIA-backed plot to assassinate Fidel Castro in the early 1960s. He is also linked to allegations of meddling in the 1960 U.S. presidential election.
How did Sam Giancana's life end?
Giancana died on June 19, 1975, in Oak Park, Illinois, at the age of 67. He had been living in relative obscurity following his early-1960s conviction for income tax evasion.
Why is Sam Giancana significant in crime history?
He is one of the most recognizable figures in American organized crime because of his long tenure as Chicago Outfit boss and his alleged entanglements with federal intelligence agencies. His name remains central to discussions of mob, politics, and CIA overlaps during the Cold War era.
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