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    Sinatra in 1941
At first, the FBI had nothing going on Sinatra. That would change.
(Recording with Tommy Dorsey in New York, 1941/AP)
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'Psychoneurosis, Severe'
Continued from preceding page

When the FBI started its Sinatra files, the singer was cresting his first great peak of fame. Earlier in 1943, he had had his first monster hit, "All or Nothing at All." That spring he had made his second smash appearance at the Paramount Theater in New York. The day after the letter about the whistling sound arrived in Washington, he conquered the West Coast with a triumphant appearance at the Hollywood Bowl. He was "Swoonatra," the Leonardo DiCaprio and Michael Jackson of his time rolled into a package that is hard to imagine today.

As such, he was fodder for the gossip columnists, and this is where his trouble truly started. One of the revelations of the files is how big a role newspapermen played in stalking him.

"December 30, 1943

"Dear Mr. Winchell:

"I don't dare give you my name because of my job but here is a bit of news you can check which I think is Front Page:

"The Federal Bureau of Investigation is said to be investigating a report that Frank Sinatra paid $40,000.00 to the doctors who examined him in Newark recently and presented him with a 4-F classification. The money is suppose to have been paid by Sinatra's Business Manager. One of the recipients is said to have talked too loud about the gift in a beer joint recently and a report was sent to the F.B.I.

"A former School mate of Sinatra's from Highland, N.J., said recently that Sinatra has no more ear drum trouble than Gen. McArthur."

In fact, the FBI had nothing going on Sinatra, but the letter became in effect a self-fulfilling prophecy: After Winchell passed it on, the bureau in February 1944 opened its second Sinatra file, #25-244122, a "limited inquiry." The bureau found that the Army doctor who had examined Sinatra would "stake his medical reputation" on his findings concerning the singer's ear.

The file includes a portion of the doctor's report not previously disclosed:

"During the psychiatric interview," the doctor wrote, "the patient states 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 somatic ideas and headaches and has been very nervous for four or five years.' " Because Sinatra had already been rejected for his punctured eardrum, the doctor wrote, a diagnosis of "psychoneurosis, severe" was euphemized in the official record as "emotional instability" to avoid "undue unpleasantness for both the selectee and the induction service."

There is no indication that the FBI was even slightly skeptical that a man who nightly faced some of the most raucous crowds in show business history could have such an extreme fear of people.

As part of this inquiry, the FBI also discovered Sinatra's 1938 arrest on what was known in those days as a "morals charge" – that he slept with and then discarded a woman he had allegedly promised to marry. The woman was already married, and the charge went nowhere. It had made the press in Hudson County, N.J. – "Songbird Held in Morals Charge" – but the FBI did not catch up with it until six years later.

The files do show that FBI agents were assiduous readers of syndicated gossip columnists. A February 1944 column by Frederick C. Othman said an FBI official had sent Sinatra a letter with a postscript asking for autographed pictures for "the girls" in his office. The FBI contacted Sinatra, who said the columnist had made a mistake.

In June 1944, Winchell wrote that the singer had asked that no pictures be taken of his son, because he had received kidnapping threats. Again the FBI contacted Sinatra, who said, again, that the columnist had made a mistake.

Still, the FBI created file #9-11775, "Kidnapping Threats Received by Frank Sinatra."

In May 1945, Sinatra made a 10-minute film titled "The House I Live In," in which he delivered a message of racial and religious tolerance and sang the title song. The short earned Sinatra a special Academy Award, which he once said was his most treasured honor in a lifetime of honors.

Six months after Sinatra made the film, the FBI's Philadelphia office received the bureau's first tip that he was a member of the Communist Party. As a New Deal Democrat who had visited FDR in the Oval Office, Sinatra was already close to several groups that the FBI in the emerging Cold War would consider Communist fronts. The files say that Sinatra "reportedly had been associated with or lent his name" to 16 such fronts.

A typical "subversive" association from the FBI files: "An article appearing in the Baltimore Afro-American dated April 10, 1945, reflected that Frank Sinatra was to give a talk on racial harmony. It stated that Sinatra was reported to have beaten several Southern cafe owners who refused to serve Negro musicians in his party."

In January 1946, the anti-Communist radio commentator Gerald L. K. Smith fired the first public salvo at Sinatra. Smith appeared before the House Un-American Activities Committee and said Sinatra was a "front" for Communist groups. He called for an investigation of the singer for his alleged support of a banquet for American Youth for Democracy (AYD), an organization branded by Hoover as the successor to the Young Communist League and "one of the most dangerous outfits in the nation."

Sinatra was never hauled before HUAC. He briefly argued against the tide of anti-Communist hysteria the committee inspired – "Once they get the movies throttled, how long before the committee gets to work on freedom of the air?" he reportedly said – but aside from supporting a few broadcast rallies in favor of free speech, he did not take on HUAC directly.

The files show Sinatra as little more than a liberal do-gooder who had aroused the FBI's paranoia. In March 1946 FBI agents eavesdropped on a phone conversation between a Sinatra representative and AYD. The group wanted Sinatra to write a 500-word article on "Discrimination"; Sinatra's man said Sinatra's beliefs did not run "towards communism." The article was never written. Yet the exchange was reported in the files as another of Sinatra's subversive links.

On February 11, 1947, Sinatra flew down to Havana with Joe ("Joe Fish") Fischetti and his brother Rocco, members of Al Capone's Chicago gang, and met with Lucky Luciano, the father of the modern Mafia. Sinatra and Luciano were spotted together at a casino, a racetrack and at parties.

Within days, Scripps-Howard columnist Robert Ruark, who happened to be in Havana, broke a story headlined, "Sinatra Is Playing With the Strangest People These Days." Hearst columnists Westbrook Pegler of the New York Journal-American and Lee Mortimer of the New York Daily Mirror, who had been thumping Sinatra for "draft-dodging" and being "pink," now began zinging him for being mobbed up. (In August 1951, Mortimer would report in the American Mercury that on their Havana trip with Sinatra, the Fischetti brothers delivered unto Luciano $2 million "in the hand luggage of an entertainer." The allegation, which reportedly came from the Federal Bureau of Narcotics, was never proved.)

Within a week after Ruark's story appeared, the first FBI summary of the Sinatra files appeared: This marks the first time the bureau formally reviewed the information it was collecting, and indicates interest at the bureau's highest levels. The 4½-page document had three paragraphs about the mob and 20 about subversive groups. The mob part was slight: Willie Moretti, a New Jersey mob boss, had "a financial interest" in Sinatra, according to a local police captain. Sinatra had visited the mother of the Fischetti brothers in Chicago. Joe Fischetti had asked Sinatra to "expedite" hotel reservations for the Army-Notre Dame football game. Mickey Cohen was trying to get in touch with Sinatra. Bugsy Siegel wanted him to sing at the Flamingo Hotel opening in Las Vegas.

Hoover didn't seem to care about the mob allegations. After he read the memo, his only response was to ask if three of the links to supposedly subversive groups were "provable." Two months later, he was told that only one held true: Sinatra had received "a scroll of appreciation for his contribution to the youth of America" at a Jewish community center in Detroit. The only thing subversive about the affair was that the award had been arranged by a suspected Communist.

On April 8, 1947, Sinatra slugged Mortimer outside Ciro's nightclub in Hollywood. On May 13, Clyde Tolson, the FBI's associate director and Hoover's closest friend, wrote a memo to his boss:

"I talked this afternoon to Mr. Lee Mortimer ... who wanted to ask some questions concerning Frank Sinatra. I told Mr. Mortimer that, of course, he realized that we could not give him any official information or be identified in this matter in any manner, which he thoroughly understands."

Tolson, however, reported that he offered guidance on Sinatra's morals charge and draft record. "Conceivably the New York Mirror might have access to the records at Local Board No. 19 for Hudson County, Room 308, 26 Journal Square, Jersey City, New Jersey," read an FBI memo written to prepare Tolson for his meeting with Mortimer. But the columnist already knew about the sex and draft business; he wanted help on the mob stuff. Tolson referred him to a police captain in Bergen County, N.J.

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