Law enforcement

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

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.