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    Sinatra in 1960
By 1960, Sinatra had been brought fully into the swirl of events surrounding John F. Kennedy, intensifying the FBI's interest.
(With Peter Lawford and Marilyn Monroe, about 1960/MPTV)
Page 4
The Singer and the Senator
Continued from preceding page

On July 13, 1960, the FBI produced a confidential report on Kennedy's background, relations with the FBI and political views ("tempers his political liberalism with enough realistic conservatism"). Under "miscellaneous," the FBI reported that he and Sinatra had partied together in Palm Springs, Las Vegas and New York, and noted that Confidential magazine "is said to have affidavits from two mulatto prostitutes in New York." Informants said Sinatra was wooing JFK through Peter Lawford "so that Joe Fischetti and other notorious hoodlums could have an entre [sic] to the Senator."

After JFK won the election, Sinatra sang and escorted the new first lady at Kennedy's inaugural gala. Just over a year later, the FBI stumbled onto a secret that could have destroyed his presidency.

The Sinatra files carry only one reference, buried in a 76-page summary:

"A Bureau memo, 2/26/62, regarding 'John Roselli' stated that a review of the telephone calls of Judith E. Campbell, an associate of Roselli, revealed four calls in Dec., 1961, to the Palm Springs, Cal., residence of Frank Sinatra (purpose of the calls not stated)."

Seldom has a bombshell been cloaked in greater understatement.

The reference arose from the FBI's check of phone records for Giancana; Roselli, a gangster associate of Giancana's; and Campbell. The FBI found that the 25-year-old Campbell had one of the most interesting little phone books in history: She was contemporaneously in contact with Giancana, Roselli, Sinatra and Evelyn Lincoln, John F. Kennedy's personal secretary at the White House. It didn't take the bureau long to add two and two and arrive at four: Campbell was a link to Sinatra, Roselli, Giancana and the president.

She had been JFK's girlfriend for two years. Sinatra had introduced Campbell to JFK on February 7, 1960, when Kennedy caught the Rat Pack show at the Sands's Copa Room in Las Vegas. Sinatra had introduced her to Giancana the following month, at the Fontainebleau Hotel in Miami Beach, which had become a sort of clubhouse for the singer and the mob.

Now it was catching up with Kennedy. The day after the bureau memo noting Judith Campbell's calls to Sinatra, Hoover sent a memo of his own – to Attorney General Robert F. Kennedy, the president's brother, detailing the results of the FBI's investigation. Soon after that, the president backed away from Sinatra.

The episode became legendary: JFK, who was already scheduled to visit Palm Springs that March, switched his stay from Sinatra's house to that of Bing Crosby, a Republican.

Investigative journalist Seymour M. Hersh and others have reported that Campbell was not merely a friend to both JFK and Giancana, but also a courier between them, ferrying messages about a secret plot to kill Castro. Hersh reported in The Dark Side of Camelot that Giancana mobilized the mob to help get Kennedy elected in 1960. Sinatra reportedly was the conduit to Giancana. On some of the FBI's wiretaps of Giancana, there was discussion among mobsters of getting the singer to ask the Kennedys to lay off Giancana.

None of that is in the Sinatra files.

Hoover's report to Robert Kennedy is not in the Sinatra files, nor are any of the now-famous wiretap transcripts in which mobsters talked about leaning on Sinatra to influence the Kennedys (including the one in which Giancana henchman Johnny Formosa suggested that Giancana "hit" Sinatra for not producing). Both the report and the transcripts came to light during congressional committee hearings in the 1970s.

Sinatra himself was never the target of an FBI wiretap. Beyond the cryptic reference to Campbell, there is only a brief aside about the Sinatra/Kennedy/Giancana relationship in a memo from 1964: "Giancana's disappointment in Sinatra's inability to get the administration to tone down its efforts in the Anti-Racketeering field," it says, "constitutes the most significant information developed." Whether Sinatra actually sought the Kennedys' help for the mobsters, the files never say.


In the fall of 1962, the renovated Villa Venice Supper Club reopened for business. The Villa Venice was in Wheeling, Ill., a city not renowned as an entertainment mecca. On the bill for its grand reopening were Frank Sinatra, Dean Martin, Sammy Davis Jr. and Eddie Fisher.

The FBI was paying close attention. The Villa Venice was reportedly owned by Giancana, and the Rat Pack was appearing in "what can only be termed a command performance," according to the FBI, while illegal gambling took place in a Quonset hut nearby. Informants also told the bureau that Giancana had a secret interest in the Cal-Neva Lodge, a casino Sinatra owned in Lake Tahoe. At the time, Giancana was one of 11 gangsters listed in the Nevada Gaming Control Board's "black book" – banned from even setting foot in a Nevada casino.

Sinatra seemed to be closer than ever to the mob. The FBI soon learned that Sinatra was seeking a $5 million loan from the Teamsters pension fund to expand the Cal-Neva. The FBI was investigating Teamsters President Jimmy Hoffa and allegations that the mob was using cheap Teamsters loans to fund its operations in Las Vegas. On January 16, 1963, FBI agents interviewed Sinatra.

The interview – the only one detailed in the files – took place in Los Angeles. Sinatra's lawyer Mickey Rudin was present. Rudin said the proposed loan was his idea. He said he got it after reading a Los Angeles Times exposé about Teamsters loans to Nevada casinos. "Both Rudin and Sinatra advised they wished to go on record that there were no under-the-table payments of any kind involved," says an FBI memo.

The issue became moot five months later: The FBI learned that the Teamsters had rejected Sinatra's application.


At this point, Frank Sinatra was the Chairman of the Board, the leader of the Rat Pack, a commercial and critical powerhouse as both a singer and an actor, a man with his own jet and his own record company. With tunes like "Luck Be a Lady" and "Come Rain or Come Shine" and albums like "Come Dance With Me" and "Ring-a-Ding-Ding," he had weathered the rock-and-roll challenge of Elvis Presley. With films as diverse as "Ocean's Eleven" and "The Manchurian Candidate," he was entrenched as a screen icon. There appeared to be nothing that he could not achieve.

But the mob allegations and the associations with Giancana finally reached critical mass in an age in which Robert Kennedy's Justice Department had declared war on the mob.

On April 24, 1963, the special agent in charge of the Los Angeles office offered a suggestion to Hoover.

"A review of information that has accrued during the years ... has shown a constant association of SINATRA with some of the more infamous individuals of modern times, i.e., during the late 40's with LUCKY LUCIANO," went the SAC's windup. " ... [A] confidential source, if established in Palm Springs concerning SINATRA would undoubtedly develop information of extremely valuable intelligence nature."

And then came the pitch: "Authority is requested to conduct a preliminary survey to determine the feasibility of a misur [microphone surveillance] installation at SINATRA's residence in Palm Springs."

A bug. The SAC wanted to bug Sinatra's house. The house that JFK and Giancana had slept in.

Five days later, Hoover denied the request. "You are reminded that all misurs must be completely justified," FBI headquarters told L.A.

Three months later, Giancana was staying at the Cal-Neva, visiting his girlfriend, the singer Phyllis McGuire. Within days, news of Giancana's stay exploded into the newspapers. For allowing a banned mobster into his casino, Sinatra would be forced to relinquish his gambling license and his interests in the Cal-Neva and the Sands Hotel.

Simultaneously, the feds made their most serious attempt to go after him.

On August 27, 1963, Dougald D. MacMillan, a lawyer with the Justice Department's Organized Crime and Racketeering Section, convened a most unusual meeting of the FBI, the IRS and the U.S. attorney's office in Los Angeles. MacMillan had been assigned to do a "review of all pertinent information in an effort to determine whether prosecution could be initiated against Sinatra."

MacMillan was a hard-charging prosecutor, one of the hounds Robert Kennedy had unleashed on the mob. He'd been building a file on Sinatra for a long time from IRS and FBI reports. An IRS investigation was already underway, and MacMillan had zeroed in on the nexus of Sinatra, Giancana and the Fontainebleau.

MacMillan had arrived in L.A. with the authority to interview Dean Martin, Sammy Davis Jr., Dinah Shore and Eddie Fisher. Before embarking on what would have been the most star-studded investigation in American history, MacMillan wanted to "solicit suggestions and organize a starting point" for the interviews.

The Sinatra files reveal what a feeble idea this was. A prosecutor present told MacMillan to nail down the documents before starting on interviews. An FBI man present reported that MacMillan did not appear to have an organized plan or clear goal.

Three days later, Hoover instructed his agents to "take no action whatever which could be interpreted as investigation of Frank Sinatra" without his specific authorization. "MacMillan is a boy on a man's errand," Hoover scrawled on a memo.

MacMillan held off on the celebrity interviews. FBI agents reviewed documents to see what they could turn up. After two months, the only thing they found was a possibly false statement Sinatra had made to the IRS in 1959, when he had denied that Giancana had been present at a party Sinatra held at the Claridge Hotel in Atlantic City. An FBI informant, identified only as a professional chorus-line dancer, said she had seen Giancana at the party. In October 1963, a federal prosecutor in L.A. determined that Sinatra's response was "an apparent, though minor violation" of law, but not enough to prosecute.

It would be the last time the FBI went after Frank Sinatra.


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