The Sinatra Files (2 page)

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 other 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.”

After the mob reportedly helped Kennedy win the election, the FBI examined the phone records of one Judith Campbell and discovered that she was mixed up with both the president and Sam Giancana—not to mention Sinatra, who had introduced her to both men on separate occasions. It wasn’t hard to figure out that she was the president’s lover, as she later acknowledged. In early 1962, Hoover laid out what the FBI knew for Attorney General Robert F. Kennedy, the president’s brother. It was a not-so-subtle suggestion that the president’s coziness with Sinatra could destroy his presidency.

JFK got the message. In March 1962, the president distanced himself from Sinatra by canceling a scheduled stay at the singer’s Palm Springs complex, staying instead at the nearby home of Bing Crosby, a rival crooner and a Republican at that. It must have hurt: Sinatra’s long-cultivated friendship with JFK was over, and the mob wasn’t happy. An FBI memo later noted that “Chicago sources have advised of Giancana’s disappointment in Sinatra’s apparent inability to get the administration to tone down its efforts in the anti-racketeering field.”

Not that Sinatra was through hanging around with tough guys. Far from it: He was so successful now, having just started the Reprise record label and flying in his own private jet, that he didn’t seem to care what people thought.

He was the Chairman of the Board.

And the head of the Rat Pack. Late in 1962, he topped the bill for
a week with fellow Rat Packers Dean Martin and Sammy Davis, Jr., at the grand reopening in suburban Chicago of the mob-run Villa Venice Supper Club. According to an FBI memo, the appearance by Sinatra’s clan was “what can only be termed a command performance” in return for past favors from Giancana. Onstage, Dean Martin even sang parody lyrics about not getting paid for the gig.

Sinatra had the red-meat crowd roaring with a typically vicious putdown of the Hearst Broadway columnist critical of his connection to JFK: “I met many, many male finks but I never met a female fink until I met Dorothy Kilgallen. I wouldn’t mind if she was a good-looking fink.”

Sinatra talked the hoodlum talk, but was he walking the walk? Many in Attorney General Robert Kennedy’s anti-mob Justice Department believed so. But hard evidence was elusive, as the FBI files demonstrate.

On April 24, 1963, the special agent in charge of the FBI’s Los Angeles office asked Hoover to consider bugging Sinatra’s home in Palm Springs. Surprisingly, Hoover promptly denied the request. “You are reminded that all misurs [microphone surveillances] must be completely justified,” said the reply.

That summer, however, the FBI got a compelling new reason to keep the heat on Sinatra. At the Cal-Neva Lodge in Lake Tahoe, a casino resort in which Sinatra held a major interest, Giancana had been spotted ensconced with his girlfriend, the singer Phyllis McGuire of the McGuire Sisters. The resulting public furor—Giancana was proscribed from the casino as a known mobster—forced Sinatra to relinquish all his gambling interests in Nevada, at both the Cal-Neva and the Sands in Las Vegas.

Soon afterward, Dougald D. MacMillan, one of RFK’s top mob prosecutors, arrived in Los Angeles with authority to “review all pertinent information in an effort to determine whether prosecution could be initiated against Sinatra.” But his Los Angeles colleagues scoffed at his grandstanding plan to start off by grilling top stars and Sinatra friends like Dean Martin, Sammy Davis, Jr., Dinah Shore, and Eddie Fisher. “MacMillan is a boy on a man’s errand,” an FBI official
scrawled on one memo. When Hoover found out about MacMillan’s plan, he called it off.

Two months later, according to FBI memos, serious consideration was given to prosecuting Sinatra for denying in an interview with the Internal Revenue Service that Giancana had attended a two-week-long party he threw at the Claridge Hotel in Atlantic City. The FBI had evidence that Sinatra was lying—the testimony of a chorus girl at the party—but the matter was dropped as an “apparent, though minor, violation of the law.” Sinatra would never have a closer brush with the FBI.

At least not in the legal sense: On December 8, 1963, two weeks after Kennedy’s assassination, Frank Sinatra, Jr., age nineteen, was kidnapped from his hotel room in Lake Tahoe and held for ransom by three men, one of them an ex-schoolmate of the singer’s daughter Nancy. Two days later, Sinatra paid nearly $240,000 to secure his son’s release; the FBI arrested the three kidnappers days later.

The FBI agents who had worked closely with Sinatra throughout the ordeal felt they had made a breakthrough with the singer. One of them, Dean Elson, the bureau’s special agent in charge for Nevada, had developed a “close personal relationship” with the star and suggested that he “might be able to induce Sinatra to help us,” according to a memo.

But once again, Tolson and Hoover wanted nothing to do with Sinatra. “I do not agree,” wrote Tolson in response to Elson’s suggestion, to which Hoover added, “I share Tolson’s views.”

Still, the kidnapping episode demonstrated that Hoover and Sinatra shared at least one thing in common: an unforgiving attitude. When a Catholic prison chaplain appealed for forgiveness on behalf of two of the kidnappers, Sinatra wrote back rejecting the suggestion as “presumptuous.” He informed Hoover of his exchange with the priest in a “Dear Edgar” letter. In his “Dear Frank” reply, Hoover was in an equally unmerciful mood, quoting a judge with approval: “It is not the criminals … that need a neuropathic hospital; it is the people who slobber over them in an effort to find excuses for the crime.”

Sinatra was entering a September of his years whose bitterness belied
the wistful tone of his similarly titled 1965 album. In 1966, according to an FBI memo, he hired a Washington public relations man to “determine the identity of the SOB” who “tagged” him as a “commie” in the 1940s. When asked why Sinatra still cared after all those years, the investigator told the authorities, “Sinatra is a very temperamental, vindictive and moody individual and has periods where he dwells on his past life.”

Within a few years of Hoover’s death in 1972, the FBI’s interest in Sinatra trailed off, and little new information was added to the files.

But in 1981, after a swing to the Republicans, a retirement, a comeback, and a fourth marriage, Sinatra privately obtained his FBI dossier under the Freedom of Information Act. He turned it over to the Nevada Gaming Control Board as part of an effort to win back the gambling license he had lost thanks to Giancana in 1963.

Though the files offered plenty of reason to be suspicious of Sinatra, they proved no illegality. Perhaps that’s why Sinatra got his license back. But it couldn’t have hurt that he once again had friends in high places: One of his character references was President Ronald Reagan, whose inaugural gala the singer had hosted the previous month.

To many, it looked like the fix was in. As with so much else in Sinatra’s life, the episode didn’t so much clear up doubts about his character as illustrate them.

Less ambiguous was Sinatra’s statement to an interviewer in 1963: “When I sing, I believe, I’m honest.”

The FBI files presented on the following pages do not refute that.

1915

December 12: Birth of Francis Albert Sinatra to Martin Sinatra and Natalie Catherine “Dolly” Garavante in Hoboken, N.J.

    
1935

September: As a member of the Hoboken Four, wins first prize on
Major Bowes and His Original Amateur Hour
.

    
1938

First important nightclub gig, as a singing waiter at the Rustic Cabin in Alpine, N.J.

charged in Bergen County, N.J., with “seduction” under a false promise of marriage (and later adultery, in the same case). Charges are later dropped.