The Sinatra Files Read online

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

  —Tom Kuntz and Phil Kuntz

  To my wife, Tracy

  —Tom Kuntz

  CONTENTS

  Introduction

  The Life of Frank Sinatra: Selected Highlights

  Editors’ Note

  Preface

  ONE: Sinatra and the Draft

  TWO: Sinatra, the FBI, and the Press

  THREE: Sinatra and Communism

  FOUR: Sinatra and the Mob—The Early Years

  FIVE: Sinatra, the Kennedys, and the Mob—The Courtship

  SIX: Sinatra, the Kennedys, and the Mob—The Estrangement

  SEVEN: Sinatra Turns Right

  EIGHT: The FBI and Sinatra the Man

  Acknowledgments

  Introduction

  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 Along with a limited number of historical documents from other sources, the files have been organized and supplemented with explanatory notes to put them in context and to highlight their revelations.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 th
e 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.

  Public disaffection increased after the Scripps-Howard columnist Robert Ruark denounced him in February 1947 for having flown to Havana with two members of Al Capone’s Chicago gang and socializing there with the deported gangster Lucky Luciano—hard evidence of Sinatra’s growing tendency to associate with tough guys.

  The FBI files soon began detailing Sinatra’s mob ties, and his press detractors were in high dudgeon. Mortimer, the Mirror’s film editor, was relentless, sarcastically opining that It Happened in Brooklyn “bogs down under the miscast Frank (Lucky) Sinatra, smirking and trying to play a leading man.”

  On April 8, 1947, Sinatra struck back, literally, socking the diminutive Mortimer when they came across each other at Ciro’s nightclub in Hollywood. A month later, in one of the FBI files’ most telling episodes, Mortimer met with Clyde Tolson, Hoover’s right-hand man and best friend, to find out what the bureau had on Sinatra. Tolson informed Hoover by memo that he had told Mortimer he couldn’t give him “any official information,” yet the memo itself seems to suggest that Tolson had been helpful. Later, Mortimer reported that Sinatra had delivered $2 million in cash to Luciano in his luggage while in Havana. Often repeated, this charge isn’t backed up by anything in the FBI files.

  By this time, Sinatra’s career was going to the dogs: He performed a canine howl on the novelty song “Mama Will Bark.” In 1950, Louis B. Mayer had fired him from MGM after the intemperate star had joked too loudly that the mogul’s horseback-riding injury actually resulted from falling off his mistress, Ginny Simms.

  As if the draft-dodging, commie, and mob allegations weren’t enough, Sinatra’s marriage collapsed in the midst of a tumultuous affair with his second-wife-to-be, Ava Gardner, during which the singer attempted suicide. Coupled with his mercurial behavior, all this made Sinatra almost radioactive in show business. Performing at the Copacabana in New York while ravaged from stress, The Voice gave out as Sinatra strained to reach a high note during “Bali Hai.” He’d suffered a throat hemorrhage.

  Sinatra may have been desperate to relieve the pressure. On September 7, 1950, a colleague informed Tolson in a memo that a Sinatra go-between was trying to meet Hoover “with a proposition Sinatra had in mind.” Since “subversive elements” with whom Sinatra had been linked “are not sure of his position,” the singer “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.” Perhaps wary of Sinatra’s sincerity, Tolson scribbled at the bottom, “We want nothing to do with him,” to which Hoover added, “I agree.”

  But Sinatra’s career began a phenomenal resurgence in 1953 with his Oscar-winning turn in From Here to Eternity. Soon afterward, the singer tried to join a troupe traveling to Korea to entertain soldiers at Christmastime. The army, however, said no, citing his alleged Communist affiliations. Responding to suggestions that the rejection was based on information supplied by the FBI, Hoover’s handwritten notation on a memo ordered subordinates to “nail this down promptly.”

  Agents looked into the matter and later reported on a bizarre meeting in which Sinatra tried to persuade three army generals to let him sing for the troops. One general congratulated Sinatra on his fine performance in From Here to Eternity—a movie that was probably more subversive than Sinatra himself ever was, for it was about infidelity, indiscipline, and brutality in the military. “I am just as communistic as the Pope,” Sinatra told the generals, to no avail.

  Yet the FBI persisted in trying to dig up “subversive information” on Sinatra as agents tried to prove that he lied in denying Communist affiliations to get a passport. Finally they gave up, and Hoover concluded in a memo that despite repeated “nonspecific associations” of Sinatra’s name with the Communist party, “the investigation failed to substantiate any such allegation.”

  Not that it mattered much. By the mid-1950s, Sinatra was back on top. A collaboration at Capitol Records with the arranger Nelson Riddle was yielding the best work of Sinatra’s career, albums of swing and sophistication, including In the Wee Small Hours (1955) and Songs for Swingin’ Lovers (1956). He followed his Oscar success with memorable roles in, among oth
er films, Suddenly (1954), in which he played a would-be presidential assassin—an eerie foreshadowing of Jack Kennedy’s murder.

  The FBI’s interest in Sinatra might have receded but for his mob associations, which if anything were growing. In 1954 he had bought a 2 percent stake (later increased) in the Sands Hotel in Las Vegas, which reputedly had mob backers. He was seen with Joe Fischetti, one of the mobsters he had accompanied to Havana, and was especially friendly with Sam “Momo” Giancana, the Chicago mob boss who had interests in many of the clubs where Sinatra had performed.

  But what really got the FBI’s attention was his growing closeness to the rising young senator from Massachusetts who was running for president. Senator John F. Kennedy had even adopted Sinatra’s “High Hopes” as his 1960 campaign theme song. Sinatra, for his part, badly wanted a place in Camelot. After hiring Maltz, the screenwriter for The House I Live In, who was now blacklisted, to do a script for another movie, Sinatra bowed to pressure from the Kennedys, first by delaying the news until after the 1960 New Hampshire primary and then jettisoning Maltz altogether.

  Hoover received regular reports on all this and more. On March 22, 1960, an informant told the FBI that Confidential magazine was investigating a rumor that Senator Kennedy had attended “an indiscreet party” at Sinatra’s Palm Springs home. Later the FBI noted that Sinatra and Kennedy had partied together in New York, too, and that Confidential reportedly had “affidavits from two mulatto prostitutes in New York.” In Las Vegas, the FBI heard that “show girls from all over town were running in and out of the senator’s suite” and that “Kennedy had been compromised with a woman.”

  According to FBI informers, the mob was looking for an in with the next president of the United States. As one memo put it, the mob wanted Sinatra to use his show-biz friendship with Kennedy in-law Peter Lawford to get close to Jack Kennedy “so that Joe Fischetti and other notorious hoodlums”—Sinatra’s pals—“could have an entrée to the Senator.”