Frank Sinatra had tons of admirers and followers over his career, but there was one persistent group of fans he probably could have done without. As Erin Blakemore of History tells us, we're talking about none other than the Federal Bureau of Investigation.
The FBI kept a file on Ol' Blue Eyes for over 40 years, and compiled thousands of pages on his life, contacts, and (alleged) shenanigans. They became interested in him due to the rumors of his draft-dodging, and after they decided that these were unfounded, they started looking into Sinatra's social circle. The singer's list of acquaintances included several notable mobsters, including big shot Chicago gangster Sam Giancana, the Giacalones from Detroit, and Angelo Bruno of Philadelphia. Sinatra was never prosecuted for these connections, though at one point he grew quite concerned about the mounting rumors of his association with organized crime folks. In 1950, he even approached the FBI and offered to become an informant, in a possible bid to get in their good graces. The Feds declined. After all, they were also looking into him because of his other suspicious activities, such as supposed Communist sympathies and ... his open support of the anti-racist movement? Truly, it was a different time.
Still, the FBI was also known to assist Sinatra on occasion. The most high-profile one of these was in 1963, when the Bureau caught the three men who had kidnapped the singer's son, Frank Jr.
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