Las Vegas Sun

May 20, 2024

FBI Files Dish Dirt on Sinatra

Francis Albert Sinatra -- draft dodger? The allegation, however unfounded, is there.

Ol' Blue Eyes, friend of the mob? There too.

The Chairman of the Board, a would-be FBI special agent? His offer is included, in black and white for the public to finally see.

The FBI released all but 25 pages of its files about Sinatra on Tuesday, following a Freedom of Information request from The Associated Press and other news organizations. Sinatra himself saw the material after filing his own requests in 1979 and 1980. He died in May at age 82.

The Sinatra family had no comment on the public release of the documents said spokeswoman Susan Reynolds.

The FBI opened its file in February 1944, after gossip columnist Walter Winchell passed along a tip that the breadstick-thin singer had paid a doctor $40,000 to give him a phony 4-F draft rating.

The agency investigated and concluded "that Sinatra was suffering from an ear ailment and that his rejection was in conformance with the then-existing Selective Service regulations."

The papers, however, include a report stating that Sinatra's mental condition also made him unsuitable for military service.

One examiner wrote: "During the psychiatric interview, the patient stated that he was 'neurotic,' afraid to be in crowds, afraid to go in the elevator, makes him feel that he would want to run when surrounded by people. He had comatic ideas and headaches and has been very nervous for four or five years."

Over the ensuing years, the file filled up with allegations that were similarly sensational -- and often unfounded. The hand-typed pages released Tuesday are full of redactions, black marks used to cover the names of innocent parties.

A Sept. 7, 1950, confidential memorandum showed Sinatra offering his assistance to the FBI. Using an unidentified go-between, the Hoboken, N.J., native told FBI officials that he felt there was an opportunity to "do some good for his country under the direction of the FBI," the memo said.

The singer, the memo continued, was "willing to do anything even if it affects his livelihood and costs him his job."

A February 1947 memo, rounding up all the FBI's information on Sinatra to that point, offered a section titled "Association with Criminals and Hoodlums."

It briefly mentioned a Sinatra meeting with Benjamin "Bugsy" Siegel and a gift of a dozen shirts from a Chicago mob acquaintance of Al Capone. It also talked about Sinatra running around with reputed Chicago mobster Sam Giancana and Miami underworld figure Joseph Fischetti.

"In July 1959, it was reported that Sinatra and singer Dean Martin flew to Miami, Fla., from the West Coast to attend the wedding" of Giancana's daughter, said another entry.

Yet other memos mention the friendship between Sinatra and President Kennedy and unsavory allegations of their parties in Palm Springs, Washington and Miami. There is no mention of a woman rumored to be Kennedy's mistress, Judith Exner, nor her own alleged relationship with Giancana.

The FBI's sources for some allegations were less than impeccable. Columnist Lee Mortimer of the New York Daily Mirror met with J. Edgar Hoover's right-hand man, Clyde Tolson, for a 1947 discussion of Sinatra -- the same year that Sinatra punched the newspaperman.

Tolson steered Mortimer to the right place for information on Sinatra's 1938 arrest on seduction charges. Mortimer turned over a picture of Sinatra and another man, taken in Cuba, in hopes the FBI could identify the man as a mobster.

Sinatra's mug shot, taken by the Bergen County Sheriff's Office in 1938, was included among the released files. The charge was later dropped.

The FBI never bugged Sinatra, although an April 1963 memo indicates they did consider putting a device into the entertainer's Palm Springs, Calif., home. The idea was shot down.

There are virtually no Sinatra documents after 1980, when his friend and fellow Republican Ronald Reagan was elected president.

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