Celebrity FBI Scrutinized Sinatra By Stephen M. Silverman Published on September 7, 1998 12:00 AM Share Tweet Pin Email Eight months after his death in May of 1998, Frank Sinatra’s 1,275-page FBI file landed on the desks of New York Times editor Tom Kuntz and Wall Street Journal reporter Phil Kuntz, who have edited it down for a new book called “The Sinatra Files” (and which is excerpted at length in today’s Journal). Providing fascinating details about the life of one of the past century’s greatest entertainers, the file includes information on Sinatra’s notorious womanizing and dispels the old rumor that he paid $40,000 to the draft board to avoid serving in World War II (in fact, he had a legitimate excuse not to serve: a perforated eardrum). The file also further bolsters his already well-documented association with mob figures. Chicago mob boss Sam Giancana claimed that Ol’ Blue Eyes promised to ask President Kennedy or Kennedy patriarch Joseph Kennedy to make attorney general Robert Kennedy lighten up on his investigation of organized crime. Sinatra never did bring up the matter with the Kennedys, leaving Giancana to stew in his own juices.