Francis “Frank” Albert Sinatra appears in several FBI files. He was the target of many extortion attempts and was investigated for his connection in racketeering schemes and early involvement with Communist Party. The dates of these investigations fall between 1943 and 1985. On August 13, 1943, the Bureau received a letter that would cause them to focus much of their attention on the popular crooner of the day. The letter suggested that Frank Sinatra was using his popularity and unique singing style to brainwash young people. The letter even compared Sinatra and his “techniques” to those of Adolf Hitler. When the suspicions that Sinatra was involved with Communists faded in the 50s, the Bureau chased leads that could trace Sinatra back to the Mob or domestic terrorist organizations. With a file that spanned four decades, Sinatra would come to be called “the most investigated performer since John Wilkes Booth.”
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