Sinatra Files: Blue-Eyed Stew

Singer, actor, nightclub star. Frank Sinatra was all of those things, and he also was a target of the FBI. CBS News Correspondent Eric Engberg reports on documents that show what the government knew and what it thought it knew about Sinatra.

The FBI came up with 1,300 pages of information on Sinatra, and released all but 25 of them.

The skinny baritone from Hoboken was the darling of the bobby-soxers when the FBI opened its first file on him. On a tip from J. Edgar Hoover's pal, gossip columnist Walter Winchell, the bureau chased a false report that Sinatra had bought his way out of the World War II draft.

Young Sinatra at the mike (CBS)
Not so, the doctors told agents. Sinatra had a perforated ear drum, a medical disability. To top it off, the man who would go on to become a legendary bon vivant complained of being tired a lot and afraid of crowds. The draft doctors diagnosed emotional instability, but were afraid to put that in their written report because of Sinatra's fame.

But it began a 40-year FBI infatuation with the greatest entertainer of his generation.

The files are available to the public now because Sinatra is dead. Long believed to be friendly with such organized crime bosses as the notorious Sam Giancana, Sinatra is frequently mentioned in FBI reports on the mob. But the agents never found evidence of a crime in his mob connections.

For his part, Sinatra maintained in an exclusive CBS interview with Walter Cronkite that it was just part of being an entertainer: "In theatrical work, in nightclub work, in concerts. So, wherever I might be. In restaurants, you meet all kinds of people, so that there's really not much to be said about that. And I think the less the better."

Curiously, there is no mention in the Sinatra files of Judith Exner, the Giancana and Sinatra girlfriend who has claimed she engaged in a long love affair with President Kennedy, which could have compromised the government's attack on the mob.

In 1963, the FBI chief in Los Angeles requested permission to survey Sinatra's home in Palm Springs to see if it could be bugged with the goal of developing "information of extremely valuable intelligence nature and furnish a picture of top-level criminal investments and operations." FBI boss Hoover scotched the plan as "inadvisable at this time."

There's no indication the bureau ever did any bugging of the man called The Chairman of the Board. His magic voice doesn't grace a single FBI surveillance tape.

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Sinatra with the Reagans (AP)
After 1980, the files show the FBI losing interest in Sinatra altogether. By then, he was an entertainment idol, and a friend and important supporter of President Reagan.

When Sinatra died 7 months ago at 82, he knew everything the FBI knew about him. He had obtained copies of all the FBI files by using the Freedom of Information Act, 18 years before his death.

Among the other papers on Sinatra:

  • A federal report on the plane crash that killed Sinatra's mother, Dolly
  • A report of a 1966 bomb threat against Sinatra in Miami Beach
  • A 1969 death threat in which Sinatra was given the option of a $2 million donation to the Vatican in return for his life.
The sender of the last letter was not prosecuted, but turned over for psychiatric care.