7. Frank Sinatra associated with mob figures, but he wasn’t a spy
Frank Sinatra is often reported on websites as being both a spy for the FBI and an informant about his various mob connections. His FBI file details his many connections with mob figures, including Sam Giancana, whom Sinatra considered a close friend. Mob figures were frequent guests in his home and at his performances, from the early 1940s until the end of his life. The FBI eventually held a file on the entertainer which contained thousands of pages, among them their rejection of his offer to serve as a confidential informant. The FBI flatly rejected the offer, writing across a report of one such meeting, “We want nothing to do with him”.
Sinatra received an exemption from the draft during World War II, for “psychological reasons” as well as a punctured eardrum. Though the FBI file lists his exemption as legitimate, he often joked about it to friends during and after the war. The websites which claim he spied for the government make their assertions based on hearsay and support them with little evidence. Some claim he used his private plane to whisk people in and out of the country at the behest of the CIA or other government agency. But no evidence exists to support the claims. Twice in his lifetime Sinatra used the Freedom of Information Act to gain access to the file the FBI had on him, but he did nothing to challenge the documentation and continued to consort with Mafiosi until the end of his life.