Sam Giancana: Mafia Playboy, Political Kingmaker, Marked Man | Rogues Gallery | Full Episode

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Rogues Gallery

Episode 7 - Sam Giancana - Boss of Bosses

Step into the hidden world of organized crime with the story of Sam “Momo” Giancana, one of the most notorious mob bosses of the 20th century. Rising from Chicago’s tough neighborhoods during Prohibition, Giancana built an empire through gambling, racketeering, and high-profile connections to Hollywood stars and political figures. His ties to Frank Sinatra, the Rat Pack, and even the Kennedy family made him a household name—and a top target for the FBI and Attorney General Robert Kennedy.

This documentary traces Giancana’s climb to power, his turbulent relationship with the Chicago Outfit, and the relentless federal investigations that followed him. It also explores his rumored involvement with the CIA’s Cold War operations and the conspiracy theories linking him to major historical events. From the glitz of Las Vegas to the corridors of Washington, Sam Giancana’s story reveals how organized crime shaped American history—and how one man’s pursuit of power ultimately led to his downfall.

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