Sam Giancana
Chicago Outfit boss tied to CIA and presidential politics.
Salvatore "Mooney" Giancana—born Gilormo Giangana on May 24, 1908, in Chicago—ran the Chicago Outfit from 1957 until 1966. His parents were Italian immigrants from Sicily. As a teen, he joined the 42 Gang, a street crew tied to political boss Joseph Esposito. The gang’s name came from Ali Baba and the 40 Thieves; they thought they were one better. Giancana quickly became known as a skilled getaway driver, a big earner, and a violent enforcer. After Esposito was murdered—Giancana was allegedly involved—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. He moved up to triggerman, and by age 20 he was the main suspect in three murder cases but never tried. In 1929, he was convicted of burglary and larceny and served three years and nine months at Joliet Correctional Center. In the late 1930s, he became the first 42er to join the 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 used ties to New Orleans boss Carlos Marcello to control liquor licenses. In 1939, Giancana was convicted of bootlegging and got four years in Leavenworth and Terre Haute.
After his release in 1942, he made his mark by convincing Accardo—then the Outfit’s underboss—to take over Chicago’s black lottery payout system. Giancana’s crew allegedly forced Eddie Jones out of the racket and out of the country. They also murdered gambling boss Theodore Roe on August 4, 1952. Roe had refused to hand over his operation; a year earlier, on June 19, 1951, he had killed Giancana’s made man Leonard Caifano. The takeover wasn’t complete until Jackie Cerone scared “Big Jim” Martin to Mexico with two bullets to the head that didn’t kill him. The lottery game brought in millions yearly for the Outfit, and that success helped get Giancana named boss in 1957. Accardo and Ricca stepped back to consigliere roles, but everyone knew they still held the real power—Giancana had to check with them on all major decisions.
Giancana was at the 1957 Apalachin meeting in upstate New York. When police stumbled on it, he stayed inside the house and avoided arrest, unlike many who fled. Later, Buffalo boss Stefano Magaddino and Giancana were caught on a wiretap saying the meeting should have been in Chicago. Giancana claimed the area was “the safest place in the world” for a mob meeting because he had several police chiefs on his payroll—they had it “locked up tight.”
Associate Hyman Larner helped expand Outfit gambling and smuggling to Panama and Iran, moving the Miami operation to Panama for easier money laundering. These operations were a partnership between the Mafia and the CIA. By 1966, that partnership had grown into arms smuggling to the Middle East for the Israeli Mossad, all via Panama. Corrupt cop Richard Cain made frequent trips to Mexico as Giancana’s courier and financial adviser.
Some sources say Giancana and the Mafia helped John F. Kennedy win the 1960 presidential election. In the 1960s, the CIA recruited him for a plot to kill Fidel Castro. In 1965, he was convicted of contempt of court and served a year in prison. After release, he fled to Cuernavaca, Mexico. He was deported back to the U.S. in 1974 and returned to Chicago. On June 19, 1975, just before he was to testify before the Church Committee, Giancana was murdered at his home in Oak Park, Illinois.
- 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 (1957–1966); alleged involvement in 1960 presidential
Verified Timeline
Quick Facts
- Birth Name
- Gilormo Giangananame="birth name" · group="nb"
- Birth Date
- 1908-05-24name="birth date" · group="nb"
- Birth Place
- Chicago, Illinois, U.S.
- Death Date
- 1975-06-19
- Death Place
- Oak Park, Illinois, U.S.
- Death Cause
- Multiple gunshot wounds
- Resting Place
- Mount Carmel Cemetery, Hillside, Illinois, U.S.
- Other Names
- "Mooney" / "Momo" / Salvatore Giancana
- Spouse
- Angeline DeTolve · 1933 · 1954 · reason=her death
- Children
- 3
- Allegiance
- Chicago Outfit
- Occupation
- Crime boss
Facts from the source article.
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 age 20 he had been the prime subject of three murder investigations but never tried. In 1929, he was convicted of burglary and larceny, sentenced to one to five years in Joliet Correctional Center, and released in 1932 after serving three years and nine months. In 1939, he was convicted of bootlegging and sentenced to four years in Leavenworth and Terre Haute. During the late 1930s, Giancana became the first 42er to join the Chicago Outfit. After his release from prison 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 is believed to have convinced Eddie Jones to quit his racket and leave the country, and was responsible for the August 4, 1952, murder of African American gambling boss Theodore Roe. The takeover produced millions of dollars a year for the Outfit, bringing Giancana further notice and believed to be a major factor in his being anointed as the Outfit's new boss in 1957. Giancana was present at the Mafia's 1957 Apalachin meeting; he avoided arrest by staying inside the meeting house. He 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. In 1959 Giancana appeared before the Select Committee on Improper Activities in Labor and Management, where he was questioned by Chief Counsel Bobby Kennedy. Under questioning Giancana started laughing, in response Kennedy chided that "I thought only little girls giggled, Mr. Giancana." Some journalists claimed Giancana and his Chicago crime syndicate played a role in John F. Kennedy's 1960 presidential election victory. Giancana's mistress Judith Exner stated Giancana used his connections to persuade unions to support Kennedy. During the Kennedy administration, the CIA recruited Giancana and other mobsters to assassinate Fidel Castro. Giancana reportedly said the CIA and Cosa Nostra were "different sides of the same coin." In 1965, Giancana was convicted of contempt of court, serving one year in prison. After 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.
Reader's Guide
Sam Giancana's significance lies in his leadership of the Chicago Outfit from 1957 to 1966, a period marked by national political and intelligence intrigue. His alleged role in John F. Kennedy's 1960 presidential election victory, though based on claims from some sources, highlights the intersection of organized crime and presidential politics. Giancana's murder on June 19, 1975, at his Oak Park home, shortly before he was to appear before the Church Committee, underscores the violent consequences of mob involvement with state secrets. His career illustrates the Outfit's expansion into Louisiana gambling and Chicago's black lottery system, as well as international operations in Panama and Iran through associate Hyman Larner. The enduring uncertainty about his exact influence on the 1960 election and the CIA plots leaves his legacy as a figure of both criminal power and historical mystery.
Did You Know?
- Giancana was born Gilormo Giangana on May 24, 1908, in The Patch neighborhood of Chicago to Italian immigrant parents from Castelvetrano, Sicily.
- He joined the 42 Gang as a teenager; the name was a reference to Ali Baba and the 40 Thieves, thinking they were one better.
- At the 1957 Apalachin meeting, Giancana avoided arrest by staying inside the meeting house instead of fleeing like many others.
- In 1959, when questioned by Bobby Kennedy, Giancana started laughing, and Kennedy responded, '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?
Sam Giancana, born Salvatore 'Mooney' Giancana in 1908, was an American mobster who led the Chicago Outfit from 1957 to 1966. He began as a teenager in the 42 Gang before building a criminal empire spanning the Midwest and the South.
What criminal activities was Sam Giancana involved in?
He oversaw illegal gambling operations, liquor distribution networks, and political corruption schemes, particularly in Louisiana. He was also connected to a takeover of Chicago's black American lottery system.
What is Sam Giancana's connection to the CIA and the Kennedy administration?
Some sources indicate he and the Mafia helped secure John F. Kennedy's 1960 presidential win. He was subsequently recruited by the CIA to participate in a plot aimed at killing Cuban leader Fidel Castro.
How did Sam Giancana's story end?
After serving time in federal prison for tax evasion, he was released and lived out his final years in Oak Park, Illinois, where he died on June 19, 1975.
Why is Sam Giancana important in organized crime history?
He stands out as a Chicago Outfit boss who became deeply entangled with U.S. government politics and intelligence agencies, blurring the line between mob power and national security operations.
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