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    Sinatra in 1951
In 1950, his career seemingly over, Sinatra approached the FBI with an intriguing proposition: He would become an informer.
(At the Palladium, London, 1951/AFP)
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Back and Bigger Than Ever
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By 1950, Sinatra's career was in ruins. MGM had released him from his film contract, and his record sales had fallen into an abyss. Part of it was natural show business evolution: Anybody that hot was going to cool off eventually, as the ardor of the bobby-soxers faded with age. But the Commie allegations had hurt him, the mob allegations had hurt him some more, and the Mortimer incident brought the wrath of the gossip columnists. Pretty soon the word went out: Frankie was finished.

An affair with Ava Gardner had dashed his marriage to his adolescent sweetheart, Nancy Barbato. Strained from overuse, his voice had failed and blood from a throat hemorrhage had trickled from his mouth during a performance at the Copacabana in New York.

On September 7, 1950, FBI Assistant Director J.P. Mohr wrote a memo to Tolson:

"[Redacted] called at my office today after having endeavored to arrange an appointment to see the Director ... to contact the Director with regard to a proposition Sinatra had in mind ... [Redacted] stated that Sinatra feels he can do some good for his country under the direction of the FBI ... Sinatra feels that the publicity which he has received has identified him with subversive elements and that such subversive elements are not sure of his position and Sinatra consequently feels that he can be of help as a result by going anywhere the Bureau desires and contacting any of the people from whom he might be able to obtain information."

But in 1950, not even the FBI was buying Frank Sinatra.

At the bottom of the memo, Tolson wrote: "We want nothing to do with him."

Hoover added: "I agree."

Sinatra's offer did, however, spark another review of his FBI files and a 54-page summary. The subversive part now took up 38 pages, and the mob part 13.

Four years later, Sinatra was streaking toward his second great peak of celebrity. He had made a stunning comeback with his appearance as the doomed Maggio in "From Here to Eternity," which had won him the Academy Award as best supporting actor for 1953. Musically, he had been on a two-year streak of pure pop genius. His Capitol Records recordings of "I've Got the World on a String," "My Funny Valentine," "They Can't Take That Away From Me," "I Get a Kick Out of You" and "All of Me" set new standards for sophistication and made him a bigger singer than ever.

In 1950 and '52 – dark years for him – Sinatra had offered to entertain the troops overseas and been rejected. Now, in 1954, he renewed the offer, prompting a memo to Hoover from the special agent in charge in New York on October 18:

"Frank Sinatra allegedly was being booked to go to Korea this Christmas as part of a USO entertainment group ... To the surprise of Sinatra ... the Army denied clearance ... Allegedly the Army advised that it had information from the FBI which prompted the Army to deny clearance to Sinatra. This information allegedly was that Lee Mortimer in a newspaper column stated that Sinatra was a Communist. This is information which allegedly came from the Bureau's files."

To which Hoover replied, "Nail this down promptly."

Whereupon the FBI obtained an Army memorandum dated September 17, 1954. The memo detailed a meeting between Sinatra and three generals to discuss the denial of his clearance.

Gen. Alfred E. Kastner "pointed out that ... serious question existed as to Mr. Sinatra's sympathies with respect to communism, communists, and fellow travelers ... General [Gilman C.] Mudgett ... digressed to congratulate Mr. Sinatra on his fine performance in 'From Here to Eternity.' "

Sinatra told them he "hated and despised everything that pertained to communism" and said, "I am just as communistic as the Pope." He said he was going to take the matter to the attorney general "to clear his name."

Sinatra did not get his Army clearance. (The Army later admitted to the FBI that its information came from press clippings, not the bureau.) Instead, he got another review of his FBI files.

The State Department asked for the review after Sinatra applied for a passport on January 10, 1955. On his application, he swore that he had never been a member of the Communist Party. State wanted to know if he could be prosecuted for making a false statement.

The files indicate that Sinatra was distancing himself from the left: The Daily Worker had asked in 1951, "Where Are the Big Stars Who Once Opposed the Un-Americans?," singling out Sinatra's silence. Still, the Justice Department on March 7, 1955, requested a fuller investigation on State's behalf.

Sinatra was at the summit of his career. In February 1955, he had recorded "In the Wee Small Hours of the Morning." Many would consider the similarly named concept album to be his finest work. In August 1955, he would grace the cover of Time magazine, boosted by songs like "Young at Heart" and "Learnin' the Blues," and movies like "The Tender Trap" and "Guys and Dolls." "I feel eight feet tall," he told Time.

Even as the Time story appeared, FBI field offices in Los Angeles, New York, Newark, Philadelphia, Chicago, Detroit, Albany and Salt Lake City were searching their files for "subversive information" on Sinatra. The Philadelphia office, for example, was asked to recontact the informant from 10 years ago who had first identified Sinatra as a Communist.

The effort went for naught. In a letter to the Justice Department dated December 27, 1955, Hoover singled out only Sinatra's position as vice chairman of the Independent Citizens Committee of the Arts, Sciences and Professions, a group labeled as a Communist front by the California Committee on Un-American Activities.

Hoover's letter bore an internal note referring to "nonspecific associations" of Sinatra's name with the Communist Party, but the note added that the "investigation failed to substantiate any such allegations."

Sinatra's days as a subversive threat were over.

The files covering the late '50s thin out and lose their urgency. They record sightings of Sinatra with such gangsters as Joe Fischetti and Sam "Momo" Giancana, the boss of the Chicago mob. They quote an FBI informant as saying that Sinatra, for his part, had "a hoodlum complex." But by the late 1950s, Sinatra's standing was such that mob associations could no longer derail his career.

Then on March 22, 1960, an informant advised the bureau that Confidential magazine was investigating a rumor of "an indiscreet party" at Sinatra's Palm Springs home attended by Sen. John F. Kennedy and actor Peter Lawford, a Kennedy brother-in-law. The senator was campaigning hard for the presidency. Sinatra's "High Hopes" was his campaign's theme song. Gangsters were one thing; a potential president of the United States was another.

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