FBI Releases Data on Frank Sinatra

Wednesday, Dec. 9, 1998 | 9:19 a.m.

It would have happened if Ol' Blue Eyes had his way, according to a cache of confidential documents from Sinatra's FBI file, made public Tuesday. Sinatra in 1950 volunteered to work undercover for the feds -- an offer they could (and did) refuse.

That same year, according to a confidential federal informant, Sinatra smuggled $1 million cash into Italy for mobster Charles "Lucky" Luciano. Such tales are the stuff of The Sinatra Files, a mishmash of facts, allegations and just plain rumors.

The papers -- 1,275 pages in all -- offered few nuggets of new information. There were vague allegations of mob ties and communist sympathies, but little detail or evidence of either.

There's no mention of Judith Exner, the Sinatra acquaintance who allegedly had simultaneous affairs with President Kennedy and Chicago mobster Sam Giancana. No bacchanalian tales of the Rat Pack rampaging through Las Vegas. And only passing mentions of mob bosses like Giancana and Carlo Gambino, with no smoking guns.

Rather than flashes of the infamous Sinatra temper, the documents include a variety of threats against the singer - everything from extortion to death threats.

A Sept. 7, 1950, confidential memo 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."

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

The FBI started its Sinatra 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.

That charge was baseless, but the file filled up over the years.

According to the FBI, Sinatra saw the material after filing his own requests in 1979 and 1980. The FBI came up with 1,300 pages on Sinatra, and released all but 25 of the pages after Freedom of Information requests from The Associated Press and other news agencies.

But there's little revelatory about Sinatra, who died in May at age 82. A February 1947 memorandum, 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.

But even that section held just a mere five paragraphs.

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, involving an affair with a married woman. 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 the agency did consider putting a device in the entertainer's Palm Springs, Calif., home. The idea was shot down.

The files contain no information about the investigation into the 1963 kidnapping of Sinatra's son, Frank Jr. He was released after a ransom was paid, and three men were convicted.

And there are virtually no Sinatra documents after 1980, when his friend and fellow Republican Ronald Reagan was elected president. An exception was a bizarre March 1985 letter threatening to kill Sinatra, and blaming the singer for "Amtrack accidents, planes crashing ... (and) candy around Halloween being tampered with."

The writer was later interviewed by the FBI and backed off her threat.