Salvatore “Sam” Giancana was a Sicilian American mobster, notable as the boss of the criminal Chicago Outfit from 1957 to 1966. His nicknames were “Mooney,” “Momo” and “Sam the Cigar.” Take a look below for 28 more strange and scary facts about Sam Giancana.

1. Giancana was born Salvatore Giangana, in The Patch on Chicago’s West Side, to Sicilian immigrants from Partanna, in the province of Trapani.

2. His father, Antonio Giangana, owned a pushcart and briefly an Italian ice shop, which was later firebombed by criminal rivals of his son.

3. Baptized Momo Salvatore Giancana and known as Sam, he grew up in a rough neighborhood on the West Side of Chicago, as the son of Sicilian immigrants.

4. As a teenager, Giancana led a street gang called “The 42s,” who carried out low level tasks for members of the powerful Chicago Mafia of the 1920s, led by the notorious gangster, Al Capone.

5. Giancana got a job as a “wheelman,” or driver, in the Capone organization, and was arrested for the first time in 1925, for auto theft.

6. He soon graduated to “triggerman,” and by the age of 20 had been the prime suspect in three murder investigations, but never tried.

7. After Esposito’s murder, in which Giancana was allegedly involved, the 42 Gang was transformed into a de facto extension of the Chicago Outfit.

8. The Outfit was initially wary of the 42ers, thinking them too wild, but Giancana’s reputation gained him the notice of Outfit leaders such as Frank “The Enforcer” Nitti, Paul “The Waiter” Ricca, and Tony “Joe Batters” Accardo.

9. During the late 1930s, Giancana became the first 42er to join the Chicago Outfit.

10. From the early 1940s through the 1950s, he controlled most of the illegal gambling, illegal liquor distribution, and numerous other political rackets in Louisiana through longtime friend H.A. Killian. Killian controlled the majority of the liquor license issuance by his associations with longtime New Orleans business associate Carlos Marcello.

11. Giancana married Angelina DeTolve, the daughter of immigrants from the Italian region of Basilicata, on September 23, 1933.

12. They had three daughters, Antoinette, Bonnie, and Francine.

13. His wife died in 1954, leaving him to raise his daughters.

14. Giancana never remarried and was known as a good family man, despite frequent infidelities.

15. All of the Giancana daughters have married at least once. As of 1984, at least one daughter, Antoinette, had taken the Giancana name again after her divorce.

16. During 1945, after serving a sentence at the Federal Correctional Complex, Terre Haute, Indiana, during which he told his children he was away at college, Giancana made a name for himself by convincing Accardo, then the Outfit’s underboss, to stage a takeover of Chicago’s African-American “policy” payout system for the Outfit.

17. Giancana’s crew is believed to have been responsible for convincing Eddie Jones to quit his racket and leave the country.

18. Giancana’s crew was also responsible for the August 4, 1952, murder of African-American gambling boss Theodore Roe. Both Jones and Roe were major South Side gambling bosses.

19. Giancana was present at the Mafia’s 1957 Apalchin meeting at the Upstate New York estate of Joseph Barbara. Later, Buffalo crime boss Stefano Magaddino and Giancana were overheard by wiretap saying the meeting should have occurred in the Chicago area.

20. Giancana claimed that the Chicago area was, “the safest place in the world” for a major underworld meeting because he had several police chiefs on his payroll.

21. If the syndicate ever wanted to hold a meeting in or around Chicago, Giancana said, they had nothing to fear because they had the area “locked up tight.”

22. Some journalists claimed that Giancana and his Chicago crime syndicate “played a role” in John F. Kennedy‘s victory in the 1960 presidential election.

23. It is widely reputed and was partially corroborated by the Church Committee hearings that during the Kennedy administration, the Central Intelligence Agency recruited Giancana and other mobsters to assassinate Fidel Castro.

24. Giancana reportedly said that the CIA and the Cosa Nostra were “different sides of the same coin.” Documents released in 2017 showed the Giancana connection to the CIA and to Robert Maheu.

25. Judith Exner claimed to be the mistress of both Giancana and John F. Kennedy, and that she delivered communications between them about Castro. However, Giancana’s daughter, Antoinette, had said that her father was performing a scam to pocket millions of CIA dollars.

26. According to the declassified CIA “Family Jewels” documents, Giancana and Trafficante were contacted in September, 1960, about the possibility of an assassination attempt by Maheu after Maheu had contacted Roselli, a Mafia member in Las Vegas and Giancana’s number two man.

27. Giancana’s behavior was too high-profile for Outfit preferences and attracted too much federal scrutiny. He also refused to share his lavish profits from offshore casinos in Iran and Central America with his subordinates. Both of these factors resulted in much resentment among the Outfit’s rank-and-file.

28. Giancana was the subject of many hours of wiretaps. On one, he was heard saying, “We’re whacking a lot of the wrong guys lately.”