FBI Files on Sinatra Detail Links to JFK, Mob Figures

The FBI opened its files Tuesday on Frank Sinatra, a 1,275-page dossier documenting nearly a half-century of investigations of the entertainer--from his alleged ties to organized crime to a tip from gossip columnist Walter Winchell that he had bought his 4F draft exemption for $40,000.

A bureau inquiry found the charge relayed by Winchell to be baseless. But the files, made public under the Freedom of Information Act, detail other inquiries into Sinatra’s life, with frequent mention of his links to such notorious mob figures as Lucky Luciano and Sam Giancana.

Those associations produced no criminal charges, but reportedly were extensive enough to lead President John F. Kennedy to cool his relationship with the famed singer who died this year at 82.

The FBI launched numerous investigations related to Sinatra, including inquiries into allegations that he had links to the Communist Party and into death threats made against him.

The bureau rejected Sinatra’s offer to serve as an FBI informant, though it had accepted a similar offer during the 1940s from then-actor Ronald Reagan and his wife at the time, actress Jane Wyman. In a handwritten note at the bottom of the report, Clyde Tolson, a longtime aide to FBI Director J. Edgar Hoover, wrote: “We want nothing to do with him [Sinatra].”

The 4F inquiry was conducted in 1944 after Winchell forwarded to the FBI an anonymous letter outlining the allegations. The FBI concluded that Capt. Joseph Weintrob, the medical officer who examined Sinatra at a Newark, N.J., induction station, was justified in exempting Sinatra from military service because the singer had a perforated left eardrum and related ear problems.

During a psychiatric interview that was part of the medical exam, Sinatra described himself as “neurotic, afraid to be in crowds,” leading the examining psychiatrist to find that the bobby-soxer idol suffered from psychoneurosis.

But because Sinatra was being rejected on physical grounds, the doctor’s diagnosis was downgraded to a notation of “emotional instability” to avoid “undue unpleasantness for both the selectee and the induction service.”

The agency’s review of Sinatra’s draft status was conducted under handwritten orders by Hoover to do nothing “irregular.” In the draft report, the FBI noted that Sinatra had been arrested twice in 1938 in Hackensack, N.J.--first on charges of seduction and then on adultery. The charges eventually were dismissed, but agents added two police mug shots of the singer to the file.

The FBI dossier includes hundreds of references to Sinatra’s ties to “criminals and hoodlums.”

Relying on unnamed informants, press reports and secret surveillances, the FBI spent nearly 30 years tracking Sinatra and his associates.

Mobster Bugsy Siegel invited Sinatra to the opening of the Flamingo Hotel in Las Vegas in 1946. Luciano listed him in his address book in 1949. Giancana, Vito Genovese and Thomas Luchese were his guests in Atlantic City, N.J., in 1959. James John Warjac, who had made it to the FBI’s 10 Most Wanted List, had a picture of Sinatra dealing blackjack when Warjac was nabbed in 1960. Joe Fischetti dined with him in Miami in 1968.

Gangsters all, the FBI said.

One 1961 memo noted that Giancana and Sinatra liked to have contests to see who could spend the most money buying drinks and trinkets for their friends in Chicago.

But Sinatra told the FBI that Giancana “was only someone he recalled meeting at an airport.”

Particularly worrisome to the FBI was Sinatra’s relationship with Kennedy.

As a senator, the FBI noted, Kennedy attended “an alleged indiscreet party” with Sinatra, other guests and several prostitutes.

Even Kennedy’s campaign manager was concerned, the FBI reported being told by a reliable informant. “This worried man . . . added that there are certain sex activities by Kennedy that he hopes are never publicized. [The informant] said he learned that these parties involving the senator and Sinatra occurred in Palm Springs, Las Vegas and New York City.”

One informant told the FBI that the underworld was using Sinatra to gain access to the White House.

Indeed, the FBI noted, Kennedy called Sinatra in Atlantic City in 1962 while Sinatra was attending the wedding of Philadelphia mob boss Angelo Bruno’s daughter.

So linked to organized crime did Sinatra become that Scotland Yard cabled the FBI with an urgent request in 1970. Could the FBI brief it about Sinatra’s ties to the mob?

Sinatra was scheduled to sing at a charity performance in England that Queen Elizabeth II would attend.

“If Queen attends Sinatra will be presented to her and [British officials] fear unfavorable press may result,” a cable from a Scotland Yard commissioner stated. It is not known whether the queen actually attended.

In 1954, the Army refused to allow Sinatra clearance to entertain the troops in Korea, saying that he had failed a security clearance because “serious questions existed as to Mr. Sinatra’s sympathies with respect to communism, communists and fellow travelers.”

Incensed, Sinatra argued that he “hated and despised everything that pertained to communism.” But at the end of the meeting, the generals refused to change their minds. They did, however, compliment Sinatra on his performance in the film “From Here to Eternity,” according to a record of the meeting.