June 15, 1908 - Sam Giancana
Giancana rose through Chicago's criminal underworld to lead one of the most powerful organized crime organizations in the United States, wielding influence that extended from street-level gambling operations to the highest levels of American politics and government. His tenure as boss of the Chicago Outfit brought him into contact with both a presidential campaign and a CIA assassination plot — a reach that distinguished him from the ordinary machinery of organized crime. The breadth of his documented connections, legitimate and otherwise, made him a figure whose full significance remained contested long after his own violent death in 1975.
From Wikipedia
Salvatore "Mooney" Giancana ( JEE-ahn-KAH-nə; born Gilormo Giangana, Italian: [dʒiˈlɔrmo dʒaŋˈɡaːna]; May 24, 1908 – June 19, 1975) was an American mobster who was boss of the Chicago Outfit from 1957 to 1966.
Giancana was born in Chicago to Italian immigrant parents. He joined the 42 Gang as a teenager, developing a reputation in organized crime, which gained him the notice of the leaders of the Chicago Outfit, which he joined during the late 1930s. From the 1940s through the 1950s, he controlled illegal gambling, illegal liquor distribution, and political rackets in Louisiana. In the early 1940s, Giancana was involved in a takeover of Chicago's black American lottery payout system for the Outfit. In 1957, he became the boss of the Chicago Outfit.
According to some sources, Giancana and the Mafia were involved in John F. Kennedy's victory in the 1960 presidential election. During the 1960s, he was recruited by the Central Intelligence Agency (CIA) in a plot to assassinate Cuban leader Fidel Castro.
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