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His excuse for not serving may have been watertight, but Sinatra’s ties to known Mafia members and a revolving cast of characters connected to the underworld weren’t as squeaky clean. Sinatra’s FBI file reads like a guide to the era’s organized crime figures. Though Sinatra always denied he was connected to the mob, he did interact with famous Mafia figures like Chicago mob boss Sam Giancana, with whom he was close friends.
Sinatra supposedly introduced Giancana to John F. Kennedy‘s campaign in 1960 in an attempt to deliver union votes to the future president. According to Sinatra’s daughter, Tina, he played a gig at Giancana’s Chicago club to repay the favor. Sinatra also introduced Kennedy to Judith Campbell Exner, Giancana’s girlfriend. During the years-long affair that followed, Exner allegedly acted as a liaison between Kennedy and Giancana, helping in a plot for the Mob to assassinate Fidel Castro. (It never did, but Exner later testified before a Senate committee investigating JFK’s potential Mob ties.)