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Frank Sinatra’s Mob Ties and Other Secrets from His FBI File

May 14, 2018 in History

By Erin Blakemore

Frank Sinatra was many things: A crooner who could make bobby-soxers faint, an Academy Award-winning actor, the elder statesman of the Rat Pack. At the height of his career, it was rumored that “every woman wants to have him; every man wants to be him.” But his fans and detractors weren’t the only people who wanted a piece of Old Blue Eyes: So did the FBI.

The Federal Bureau of Investigation tracked Sinatra for over 40 years, amassing a dossier of thousand of pages about his movements, words, and friendships. The files, which were made public after Sinatra’s death in 1998, cover Sinatra throughout his tempestuous career—and read like a thrilling account of a life he lead “his way.”

Sinatra rose to fame during the 1940s, and soon attracted the attention of the FBI for claims that he’d paid a doctor $40,000 to declare him medically unfit for World War II service. Though the FBI dismissed the allegations, calling his exemption for a punctured eardrum and psychological issues legitimate, rumors that he’d dodged the draft persisted throughout his lifetime and even hurt his career in the late 1940s.

Frank Sinatra signing papers before leaving his draft board in Newark, New Jersey. Speaking of his rejection, the singer said, “I am very unhappy about it. If I had been accepted, I would have preferred the Army or Marines.” (Credit: NY Daily News Archive/Getty Images)

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 …read more


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