The Sinatra Files: The Secret FBI Dossier

Book by Kuntz Tom Kuntz Phil

When he died on May 14, 1998, Frank Sinatra was one of the most chronicled celebrities of modern times -- the focus of oceans of ink and miles of film and video footage at turns serious-minded, celebratory, or mean-spirited.

But one detailed record of his life, taken from a uniquely penetrating perspective, became fully public only after his death: the Federal Bureau of Investigation's extensive files on the singer and screen star. Most were compiled over the course of several decades under the watchful eyes of J. Edgar Hoover, as his agents investigated whether Sinatra was a draft-dodger, a Communist, or a front for organized criminals.

Released in December 1998 in response to requests under the Freedom of Information Act, the 1,275-page dossier is a trove of insights into Sinatra's life, his turbulent times, and, perhaps most important, the Hoover-era FBI's invasive and at times almost voyeuristic ways.

Although Hoover's FBI kept files on other celebrities, few were as voluminous, for no other subject was as enduring or controversial. For more than five decades, Sinatra was a major force in American society and popular culture, a politically active, hard-partying star who associated with powerful figures in both the underworld and at the highest levels of government through every important turn in the latter half of the twentieth century. The Sinatra FBI files offer themselves as an allegory of the American Century and its obsessions.

Extensive excerpts from them are published here for the first time. Along with a limited number of historical documents from other sources, the files have been organized and supplemented with explanatory notes to put them in context and to highlight their revelations.

Taken together, they invite a reassessment of the entertainer. Revelations abound. Chapter 1 details how the rail-thin crooner with impeccable phrasing at first told World War II draft board officials that he had no physical or mental disabilities, then asserted later not only that he had a perforated eardrum, which was true, but also an irrational fear of crowds, which was highly doubtful. With a blossoming career at stake, could Sinatra have been feigning mental illness? Chapter 2 includes evidence suggesting an unholy alliance between press muckrakers and the FBI's star-obsessed top brass, who occasionally helped favored journalists seeking dirt on Sinatra. This new material lends credence to Sinatra's lifelong grudge against the press.

Chapter 3 offers a disturbing glimpse into the red-baiting 1940s and 1950s, when Sinatra was unjustifiably, in his words, "tagged [as a] commie." Though for a time he stood by other embattled Hollywood stars caught up in the paranoia, he became so sensitive to the charges that, according to an intermediary, he volunteered to become an undercover snitch in the FBI's hunt for subversives. Hoover turned him down. So did the army years later, when Sinatra offered to entertain American troops in Korea.

In some key instances, what isn't in the files is as important as what is. For example, although excerpts in chapter 4 and elsewhere assiduously note Sinatra's interactions with notorious hoodlums, the FBI gathered no evidence that mob pressure landed him his Oscar-winning role as the pugnacious Private Angelo Maggio in From Here to Eternity in 1953. This canard is so embedded in the popular imagination that it is assumed to be the inspiration for a scene in The Godfather in which a severed horse's head in a movie mogul's bed ensures a plum role for an Italian-American singer. Nor do the files support the widely held assumption that the mob in 1942 strong-armed Tommy Dorsey into releasing Sinatra from a contract that entitled the bandleader to 43 percent of the singer's earnings for life.

More broadly, the files offer a striking case study of the way Hoover managed and manipulated the sensitive information at his disposal. Chapters 5, 6, and 7 detail how the FBI director, with little subtlety, made sure each successive politician who befriended the popular singer knew exactly how much derogatory information the FBI had on their friend.

John F. Kennedy's recklessness is by now well documented, but the files' dry bureaucratic account of the president consorting with associates of the very mobsters his brother the attorney general was trying to imprison will startle even the best-read Kennedy aficionados.

There also are moments of unintentional humor, as in the case of the straight-faced FBI memo that says, "Sinatra denied he sympathized with Lenin and the Marx brothers." And the capitalized names of Marilyn Monroe, Tony Bennett, and other celebrities leaven the G-men's reports like the boldface type of gossip columns.

The files also shed light on the evolving nature of Sinatra's relationship with the FBI: He eventually joined with his would-be pursuers in the bureau in a mutually respectful common cause, when Sinatra's son was kidnapped in 1963.

In sum, the files track an iconic career whose arc seems to personify postwar America's loss of innocence: Sinatra's evolution from liberal, idealistic crooner to sophisticated, sexually liberated swinger to jaded Las Vegas headliner and friend of Republican presidents.

Was the scrutiny unfair?

The FBI twice seriously considered prosecuting Sinatra, once for denying that he was a Communist and once for denying that he partied with a mobster. But despite coast-to-coast investigations, the FBI couldn't make a case against him.

Sinatra's problem throughout his career was that he never did much to remove the taint of guilt by association, especially with the mob. Judged by the company he kept, Sinatra kept inviting more scrutiny. The FBI obliged, and its files grew until the singer became, as the journalist Pete Hamill put it, "the most investigated American performer since John Wilkes Booth."