The Sinatra Files

To our parents, the late John J. and Madeleine M. Kuntz
—Tom Kuntz and Phil Kuntz

To my wife, Tracy
—Tom Kuntz

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 Along with a limited number of historical documents from other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.
chapter 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 par-tied 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.”

But in many ways Sinatra wasn’t so unique as a subject of FBI interest.
The agency kept files on thousands of people, famous and otherwise, whenever they figured in investigations, no matter how tangentially.

According to Hoover’s longtime deputy director, Cartha D. “Deke” DeLoach, the main FBI dossier on someone like Sinatra wouldn’t have been kept in the agency’s collection of “Central Files,” which were open to virtually anyone in the bureau. Instead, most of the Sinatra material would have ended up in the “Official and Confidential” files of well-known people, which were located in Hoover’s suite in two small filing cabinets behind the desk of his secretary, Helen Gandy.

There was nothing sinister in this, DeLoach maintains. In his 1995 memoir,
Hoover’s FBI: The Inside Story of Hoover’s Trusted Lieutenant
, DeLoach writes: “The purpose of keeping the O&C Files in an area of limited access was to protect the privacy of those about whom information had been gathered, not to maintain secret records for the purpose of blackmail.”

Many a Hoover chronicler would disagree with DeLoach about the sanctity of his boss’s motives, but what is undeniable is that the director often took a personal interest in the minutiae of Sinatra’s life. Readers of these pages can judge for themselves why.

The FBI began compiling the dossier during one of the most charged moments in American history—the 1940s. From the start of the Second World War, Sinatra’s rise to fame stirred an incredible amount of resentment and envy. The crooning heartthrob was thrilling millions of bobby-soxers, and making millions doing it, while avoiding the fate of the hundreds of thousands of other young men who forwent love and fortune to fight European fascism and Japanese imperialism.

As Sinatra himself noted, he was a surrogate to young women for “the boy in every corner drugstore who’d gone off, drafted to the war.” The popular historian William Manchester put it another way: “I think Frank Sinatra was the most hated man of World War II.”

And so, on the heels of pandemonium-filled appearances at New York’s Paramount Theatre, a letter arrived at FBI headquarters in
Washington. Thus began the FBI’s shadow biography of Frank Sinatra on August 13, 1943: A concerned citizen intimated darkly that a “shrill whistling sound” of shrieking bobby-soxers during a recent Sinatra radio broadcast might have been a devious technique “to create another Hitler here in America through the influence of mass-hysteria!”

Later, an FBI memo said that the columnist Walter Winchell gave the bureau a reader’s letter asserting that the FBI was investigating whether the singer had bribed his way out of the draft. The FBI wasn’t investigating any such thing, but the tip insured that it would. In February 1944, the FBI opened a “limited inquiry” that actually was far-reaching enough to dredge up records of Sinatra’s 1938 arrest in New Jersey for an alleged “seduction” under a false promise of marriage—a charge that was later changed to “adultery” after it was discovered that the supposed victim was married. That matter also was dropped, and Sinatra was free to love and leave again.

As World War II ended, Sinatra charmed his fans with songs like “Put Your Dreams Away” and frothy films like
Anchors Aweigh
, with Frank playing Gene Kelly’s wide-eyed, sailor-suited sidekick. But a serious film, all of ten minutes long, proved more important to the young singer’s career. His heartfelt plea for racial and religious tolerance in
The House I Live In
—borne of painful memories of growing up in ethnically divided Hoboken, New Jersey—won a special Academy Award and helped debunk the singer’s reputation as a frivolous, draft-dodging crooner.

The film, written by the leftist screenwriter Albert Maltz (later blacklisted), also made Sinatra a darling of the American Left and presaged the star’s association with groups the FBI deemed to be Communist fronts. It wasn’t long before an informant told the FBI (incorrectly) that Sinatra had “recently been admitted to the New York branch of the Communist Party.”

In the conservative press, Sinatra thus became, at best, a Communist-leaning “fellow traveler.” In 1946, the far-right radio commentator Gerald L. K. Smith told the House Un-American Activities Committee that Sinatra “has been doing some pretty clever stuff for
the Reds,” without backing up the charge. The committee never actively pursued Sinatra, but other conservative columnists, like Westbrook Pegler of the Hearst chain’s
New York Journal-American
and Lee Mortimer of the
New York Daily Mirror
, picked up the red-baiting cudgel against the pro-Roosevelt singer. By 1946, Hoover himself was disdainful, scrawling this unkind comment at the bottom of a memo about Detroit schoolgirls skipping school to see the star: “Sinatra is just as much to blame as are the moronic bobby-soxers.”

Later, as the bobby-soxers grew up, Sinatra’s career headed into a precipitous decline—marked by a drought of hit singles from 1948 through 1952 and dreadful films like
The Kissing Bandit
. Sinatra’s marriage to Nancy Barbato, whom he wed in 1939, was on the rocks, too, as he pursued affairs with a series of actresses.