The Infamous Mug Shot of "Bad Boy" Frank Sinatra

By Terry Claypoole

Many devoted Frank Sinatra fans are well aware of the infamous “mug shot” of 1938. This scandalous photo was first made public on December 9, 1998, when the FBI released most of Frank Sinatra’s personal file in a stunning 1300-page document. Not only was the mugshot released to the public, there were also a few shocking reports included as well. The first was a document containing reported rumors of connections to organized crime and the second included intelligence regarding his clever dodge from the military draft during World War II - a medical report that released him from military duty due to a perforated eardrum and apparent mental instability.