13 Mafia Bosses Who Defined The History Of The Mob

Published December 20, 2023
Updated April 25, 2024

Sam Giancana, The Mafia Boss With Shadowy Connections To John F. Kennedy And The CIA

Mob Boss Sam Giancana

Getty ImagesSam Giancana was allegedly involved in plots to kill Fidel Castro as well as in the Kennedy assassination.

Sam Giancana rose to power thanks to his association with Al Capone. But this Chicago gangster established a notorious reputation all his own, thanks to his connection with President John F. Kennedy.

Born in Chicago in 1908, Giancana grew up in a rough part of town and later led a gang of local youths known as the 42 Gang. Giancana’s association with the 42 Gang resulted in a long rap sheet, but it also caught the attention of Al Capone. Their fellow gangster Tony Montana told the Los Angeles Times in 2014 that Giancana and the gang were “were robbing and shaking down so many joints that Capone took notice of them.”

Working initially as a driver for Capone’s operation, Giancana steadily climbed through the ranks of the Chicago underworld, even after Capone went to prison in 1931. After his own stint in prison, Giancana consolidated his control of the Chicago Mob. And as a Mafia boss in the 1950s and ’60s, he started pulling strings on an even bigger scale.

Sam Giancana In Sunglasses

Public DomainSome say that Sam Giancana helped John F. Kennedy win the 1960 presidential election.

Connected to John F. Kennedy through Kennedy’s alleged mistress, Judith Exner, Giancana and his associates allegedly helped Kennedy get elected in 1960 by stuffing ballot boxes in Chicago. Giancana was also allegedly involved in plots to assassinate Cuban leader Fidel Castro — whom the mob despised for shutting down Mob-run casinos in Cuba — and even in the assassination of Kennedy himself in November 1963.

The United States House Select Committee on Assassinations even sought to interrogate Giancana about his possible involvement in the Kennedy assassination. But on June 19, 1975, Giancana was murdered by an unknown assailant while cooking dinner at home.

To date, no one knows if Giancana was murdered by fellow mobsters, jealous ex-girlfriends, CIA agents, or someone else entirely.

author
Kaleena Fraga
author
A staff writer for All That's Interesting, Kaleena Fraga has also had her work featured in The Washington Post and Gastro Obscura, and she published a book on the Seattle food scene for the Eat Like A Local series. She graduated from Oberlin College, where she earned a dual degree in American History and French.
editor
John Kuroski
editor
John Kuroski is the editorial director of All That's Interesting. He graduated from New York University with a degree in history, earning a place in the Phi Alpha Theta honor society for history students. An editor at All That's Interesting since 2015, his areas of interest include modern history and true crime.
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Fraga, Kaleena. "13 Mafia Bosses Who Defined The History Of The Mob." AllThatsInteresting.com, December 20, 2023, https://allthatsinteresting.com/mafia-bosses. Accessed May 19, 2024.