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A K A Frank Sinatra
The FBI kept tabs on him for 40 years, through his days as a heartthrob, a do-gooder, an associate of the Mob and a pal to the president. Reading the bureau's files is like reading into a secret history of the American Century.

By Jeff Leen
Washington Post Staff Writer
Sunday, March 7, 1999; Page M6

It began with a sound.

On August 13, 1943, a letter from San Jose arrived in Washington. The letter writer, whose identity remains a government secret, was worried about a sound that had come over the radio.

"Dear Sir:

"The other day I turned on a Frank Sinatra program and I noted the shrill whistling sound, created supposedly by a bunch of girls cheering. Last night as I heard Lucky Strike produce more of this same hysteria I thought: how easy it would be for certain-minded manufacturers to create another Hitler here in America through the influence of mass-hysteria! I believe that those who are using this shrill whistling sound are aware that it is similar to that which produced Hitler. That they intend to get a Hitler in by first planting in the minds of the people that men like Frank Sinatra are O.K. therefore this future Hitler will be O.K."

On September 2, the letter writer received a reply:

"I have carefully noted the content of your letter and wish to thank you for volunteering your comments and observations in this regard."

It was signed, "Sincerely yours, John Edgar Hoover, Director."

The FBI director's response was not merely a polite bow to wartime hysteria. His bureau used the letter about a bunch of girls cheering to open file #62-83219 "for the purpose of filing miscellaneous information" on a subject the bureau would refer to over the next 40 years as "Francis Albert Sinatra, a k a Frank Sinatra."

• • •

The letter about the shrill whistling sound sits at the bottom of a stack of paperwork now publicly known as Frank Sinatra's FBI file. The file is six inches thick, 1,275 pages long. Actually, it's a collection of files, released in a one-day blaze of publicity last December in response to Freedom of Information Act requests by 30 news organizations after Sinatra's death in May. The files, taken together, form a peculiarly American time capsule.

Spanning five decades, the documents detail the curious and complex relationship between the nation's greatest entertainer and its most powerful law enforcement agency. Born in suspicion and contempt, this relationship proved to be protean and became unexpectedly intimate – a dance of interdependence. In a strange way, Sinatra and Hoover's FBI needed each other. Sinatra gave the FBI what every law enforcement agency needs to stay engaged and in business: a threat that must be tracked. The FBI gave Sinatra what every celebrity needs: protection from lunatics and extortionists. In Sinatra and Hoover, popular culture met the politics of fear.

The files tell the story of a man who appeared, to the FBI of the 1940s, as a rare triple threat, a growing menace socially, politically and legally: Sinatra was a crooner who was corrupting America's virginal (if "moronic," in Hoover's judgment) bobby-soxers. He was a fellow traveler who crusaded for racial tolerance and consorted with Communist fronts. He was a mob associate who tantalized the feds with his comings and goings among the criminal elite.

A subject with such a résumé was unusually qualified to lead the FBI into the maze of postwar America. Sinatra would become, in journalist Pete Hamill's words, "the most investigated American performer since John Wilkes Booth." The Sinatra files offer a secret history of the American Century.

Although the bureau's concerns over Sinatra and bobby-soxers and Communists faded by the end of the 1940s and '50s, respectively, its obsession with the mob remained. The FBI could never prove anything criminal against Sinatra, but Sinatra could never remove the stain of guilt by association. The standoff only fattened the files.

In American Tabloid, the hard-boiled novelist James Ellroy explores a fictitious America seething with corruption and conspiracies and sex and celebrities. The Sinatra files cover the same turf, but with real-life characters doing real-life things. Walter Winchell and Lee Mortimer dig and dish dirt. Lucky Luciano, Bugsy Siegel and Mickey Cohen take care of business. John F. Kennedy parties. Judith Campbell dials the most interesting phone numbers. Even oft-told tales – such as Sinatra and Joe DiMaggio raiding the wrong Hollywood apartment in 1954, looking for dirt for DiMaggio's divorce from Marilyn Monroe – have a startling quality because of the names attached to them.

But in the story that emerges from the files, the big names make only fleeting appearances, like guests glimpsed at a cocktail party. There are really only two lead characters: Sinatra and the FBI, as personified, memo to memo, in the flat prose of bureau men like J.P. Mohr, Clyde Tolson and Hoover himself.

The files are filled with rumor, gossip, innuendo and raw intelligence – much of it unverified – from a variety of informants and sources, a surprising number of which are simply newspaper clippings. The information is sometimes contradictory, and rife with dated references to the "Negro Question" and "subversives" and crimes like "pandering" and "seduction." The story lines are maundering and often mundane, filled with non sequiturs and unintentional comedy ("Sinatra denied he sympathized with Lenin and the Marx brothers").

When the files were released, the instant headline was that they contained no bombshells. Still, the mass of black-and-white documents gives off a hard, cold light that brings out the fine-grained details of a life lived. In 1966, for example, a Washington PR man appeared at the Pentagon, saying Sinatra had hired him to "determine the identity of the 'S.O.B.' who 'tagged' Sinatra as a 'commie' " in the '40s. Why, the PR man was asked, did Sinatra care after all these years? The PR man replied: "Sinatra is a very temperamental, vindictive and moody individual and has periods where he dwells on his past life," the FBI files say. Is there a more succinct summary of Sinatra in the September of his years?

Reading the files is an exercise in grand irony and lost idealism. You can follow along as the archconservative cop tracks the ultraliberal entertainer. You can watch Sinatra, chastened by events, edging closer and closer to the cop. You can see Hoover coming in to block an ill-conceived wiretap plan that might have ensnared the singer (and, possibly, the president of the United States). Through a pile of federal paperwork, you can peer into one man's private life, and see how the other managed his agency's secrets.

• • •

When the FBI started its Sinatra files, the singer was cresting his first great peak of fame. Earlier in 1943, he had had his first monster hit, "All or Nothing at All." That spring he had made his second smash appearance at the Paramount Theater in New York. The day after the letter about the whistling sound arrived in Washington, he conquered the West Coast with a triumphant appearance at the Hollywood Bowl. He was "Swoonatra," the Leonardo DiCaprio and Michael Jackson of his time rolled into a package that is hard to imagine today.

As such, he was fodder for the gossip columnists, and this is where his trouble truly started. One of the revelations of the files is how big a role newspapermen played in stalking him.

"December 30, 1943

"Dear Mr. Winchell:

"I don't dare give you my name because of my job but here is a bit of news you can check which I think is Front Page:

"The Federal Bureau of Investigation is said to be investigating a report that Frank Sinatra paid $40,000.00 to the doctors who examined him in Newark recently and presented him with a 4-F classification. The money is suppose to have been paid by Sinatra's Business Manager. One of the recipients is said to have talked too loud about the gift in a beer joint recently and a report was sent to the F.B.I.

"A former School mate of Sinatra's from Highland, N.J., said recently that Sinatra has no more ear drum trouble than Gen. McArthur."

In fact, the FBI had nothing going on Sinatra, but the letter became in effect a self-fulfilling prophecy: After Winchell passed it on, the bureau in February 1944 opened its second Sinatra file, #25-244122, a "limited inquiry." The bureau found that the Army doctor who had examined Sinatra would "stake his medical reputation" on his findings concerning the singer's ear.

The file includes a portion of the doctor's report not previously disclosed:

"During the psychiatric interview," the doctor wrote, "the patient states that he was 'neurotic, afraid to be in crowds, afraid to go in the elevator, makes him feel that he would want to run when surrounded by people. He had somatic ideas and headaches and has been very nervous for four or five years.' " Because Sinatra had already been rejected for his punctured eardrum, the doctor wrote, a diagnosis of "psychoneurosis, severe" was euphemized in the official record as "emotional instability" to avoid "undue unpleasantness for both the selectee and the induction service."

There is no indication that the FBI was even slightly skeptical that a man who nightly faced some of the most raucous crowds in show business history could have such an extreme fear of people.

As part of this inquiry, the FBI also discovered Sinatra's 1938 arrest on what was known in those days as a "morals charge" – that he slept with and then discarded a woman he had allegedly promised to marry. The woman was already married, and the charge went nowhere. It had made the press in Hudson County, N.J. – "Songbird Held in Morals Charge" – but the FBI did not catch up with it until six years later.

The files do show that FBI agents were assiduous readers of syndicated gossip columnists. A February 1944 column by Frederick C. Othman said an FBI official had sent Sinatra a letter with a postscript asking for autographed pictures for "the girls" in his office. The FBI contacted Sinatra, who said the columnist had made a mistake.

In June 1944, Winchell wrote that the singer had asked that no pictures be taken of his son, because he had received kidnapping threats. Again the FBI contacted Sinatra, who said, again, that the columnist had made a mistake.

Still, the FBI created file #9-11775, "Kidnapping Threats Received by Frank Sinatra."

• • •

In May 1945, Sinatra made a 10-minute film titled "The House I Live In," in which he delivered a message of racial and religious tolerance and sang the title song. The short earned Sinatra a special Academy Award, which he once said was his most treasured honor in a lifetime of honors.

Six months after Sinatra made the film, the FBI's Philadelphia office received the bureau's first tip that he was a member of the Communist Party. As a New Deal Democrat who had visited FDR in the Oval Office, Sinatra was already close to several groups that the FBI in the emerging Cold War would consider Communist fronts. The files say that Sinatra "reportedly had been associated with or lent his name" to 16 such fronts.

A typical "subversive" association from the FBI files: "An article appearing in the Baltimore Afro-American dated April 10, 1945, reflected that Frank Sinatra was to give a talk on racial harmony. It stated that Sinatra was reported to have beaten several Southern cafe owners who refused to serve Negro musicians in his party."

In January 1946, the anti-Communist radio commentator Gerald L. K. Smith fired the first public salvo at Sinatra. Smith appeared before the House Un-American Activities Committee and said Sinatra was a "front" for Communist groups. He called for an investigation of the singer for his alleged support of a banquet for American Youth for Democracy (AYD), an organization branded by Hoover as the successor to the Young Communist League and "one of the most dangerous outfits in the nation."

Sinatra was never hauled before HUAC. He briefly argued against the tide of anti-Communist hysteria the committee inspired – "Once they get the movies throttled, how long before the committee gets to work on freedom of the air?" he reportedly said – but aside from supporting a few broadcast rallies in favor of free speech, he did not take on HUAC directly.

The files show Sinatra as little more than a liberal do-gooder who had aroused the FBI's paranoia. In March 1946 FBI agents eavesdropped on a phone conversation between a Sinatra representative and AYD. The group wanted Sinatra to write a 500-word article on "Discrimination"; Sinatra's man said Sinatra's beliefs did not run "towards communism." The article was never written. Yet the exchange was reported in the files as another of Sinatra's subversive links.

• • •

On February 11, 1947, Sinatra flew down to Havana with Joe ("Joe Fish") Fischetti and his brother Rocco, members of Al Capone's Chicago gang, and met with Lucky Luciano, the father of the modern Mafia. Sinatra and Luciano were spotted together at a casino, a racetrack and at parties.

Within days, Scripps-Howard columnist Robert Ruark, who happened to be in Havana, broke a story headlined, "Sinatra Is Playing With the Strangest People These Days." Hearst columnists Westbrook Pegler of the New York Journal-American and Lee Mortimer of the New York Daily Mirror, who had been thumping Sinatra for "draft-dodging" and being "pink," now began zinging him for being mobbed up. (In August 1951, Mortimer would report in the American Mercury that on their Havana trip with Sinatra, the Fischetti brothers delivered unto Luciano $2 million "in the hand luggage of an entertainer." The allegation, which reportedly came from the Federal Bureau of Narcotics, was never proved.)

Within a week after Ruark's story appeared, the first FBI summary of the Sinatra files appeared: This marks the first time the bureau formally reviewed the information it was collecting, and indicates interest at the bureau's highest levels. The 4½-page document had three paragraphs about the mob and 20 about subversive groups. The mob part was slight: Willie Moretti, a New Jersey mob boss, had "a financial interest" in Sinatra, according to a local police captain. Sinatra had visited the mother of the Fischetti brothers in Chicago. Joe Fischetti had asked Sinatra to "expedite" hotel reservations for the Army-Notre Dame football game. Mickey Cohen was trying to get in touch with Sinatra. Bugsy Siegel wanted him to sing at the Flamingo Hotel opening in Las Vegas.

Hoover didn't seem to care about the mob allegations. After he read the memo, his only response was to ask if three of the links to supposedly subversive groups were "provable." Two months later, he was told that only one held true: Sinatra had received "a scroll of appreciation for his contribution to the youth of America" at a Jewish community center in Detroit. The only thing subversive about the affair was that the award had been arranged by a suspected Communist.

On April 8, 1947, Sinatra slugged Mortimer outside Ciro's nightclub in Hollywood. On May 13, Clyde Tolson, the FBI's associate director and Hoover's closest friend, wrote a memo to his boss:

"I talked this afternoon to Mr. Lee Mortimer ... who wanted to ask some questions concerning Frank Sinatra. I told Mr. Mortimer that, of course, he realized that we could not give him any official information or be identified in this matter in any manner, which he thoroughly understands."

Tolson, however, reported that he offered guidance on Sinatra's morals charge and draft record. "Conceivably the New York Mirror might have access to the records at Local Board No. 19 for Hudson County, Room 308, 26 Journal Square, Jersey City, New Jersey," read an FBI memo written to prepare Tolson for his meeting with Mortimer. But the columnist already knew about the sex and draft business; he wanted help on the mob stuff. Tolson referred him to a police captain in Bergen County, N.J.

• • •

By 1950, Sinatra's career was in ruins. MGM had released him from his film contract, and his record sales had fallen into an abyss. Part of it was natural show business evolution: Anybody that hot was going to cool off eventually, as the ardor of the bobby-soxers faded with age. But the Commie allegations had hurt him, the mob allegations had hurt him some more, and the Mortimer incident brought the wrath of the gossip columnists. Pretty soon the word went out: Frankie was finished.

An affair with Ava Gardner had dashed his marriage to his adolescent sweetheart, Nancy Barbato. Strained from overuse, his voice had failed and blood from a throat hemorrhage had trickled from his mouth during a performance at the Copacabana in New York.

On September 7, 1950, FBI Assistant Director J.P. Mohr wrote a memo to Tolson:

"[Redacted] called at my office today after having endeavored to arrange an appointment to see the Director ... to contact the Director with regard to a proposition Sinatra had in mind ... [Redacted] stated that Sinatra feels he can do some good for his country under the direction of the FBI ... Sinatra feels that the publicity which he has received has identified him with subversive elements and that such subversive elements are not sure of his position and Sinatra 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."

But in 1950, not even the FBI was buying Frank Sinatra.

At the bottom of the memo, Tolson wrote: "We want nothing to do with him."

Hoover added: "I agree."

Sinatra's offer did, however, spark another review of his FBI files and a 54-page summary. The subversive part now took up 38 pages, and the mob part 13.

• • •

Four years later, Sinatra was streaking toward his second great peak of celebrity. He had made a stunning comeback with his appearance as the doomed Maggio in "From Here to Eternity," which had won him the Academy Award as best supporting actor for 1953. Musically, he had been on a two-year streak of pure pop genius. His Capitol Records recordings of "I've Got the World on a String," "My Funny Valentine," "They Can't Take That Away From Me," "I Get a Kick Out of You" and "All of Me" set new standards for sophistication and made him a bigger singer than ever.

In 1950 and '52 – dark years for him – Sinatra had offered to entertain the troops overseas and been rejected. Now, in 1954, he renewed the offer, prompting a memo to Hoover from the special agent in charge in New York on October 18:

"Frank Sinatra allegedly was being booked to go to Korea this Christmas as part of a USO entertainment group ... To the surprise of Sinatra ... the Army denied clearance ... Allegedly the Army advised that it had information from the FBI which prompted the Army to deny clearance to Sinatra. This information allegedly was that Lee Mortimer in a newspaper column stated that Sinatra was a Communist. This is information which allegedly came from the Bureau's files."

To which Hoover replied, "Nail this down promptly."

Whereupon the FBI obtained an Army memorandum dated September 17, 1954. The memo detailed a meeting between Sinatra and three generals to discuss the denial of his clearance.

Gen. Alfred E. Kastner "pointed out that ... serious question existed as to Mr. Sinatra's sympathies with respect to communism, communists, and fellow travelers ... General [Gilman C.] Mudgett ... digressed to congratulate Mr. Sinatra on his fine performance in 'From Here to Eternity.' "

Sinatra told them he "hated and despised everything that pertained to communism" and said, "I am just as communistic as the Pope." He said he was going to take the matter to the attorney general "to clear his name."

Sinatra did not get his Army clearance. (The Army later admitted to the FBI that its information came from press clippings, not the bureau.) Instead, he got another review of his FBI files.

• • •

The State Department asked for the review after Sinatra applied for a passport on January 10, 1955. On his application, he swore that he had never been a member of the Communist Party. State wanted to know if he could be prosecuted for making a false statement.

The files indicate that Sinatra was distancing himself from the left: The Daily Worker had asked in 1951, "Where Are the Big Stars Who Once Opposed the Un-Americans?," singling out Sinatra's silence. Still, the Justice Department on March 7, 1955, requested a fuller investigation on State's behalf.

Sinatra was at the summit of his career. In February 1955, he had recorded "In the Wee Small Hours of the Morning." Many would consider the similarly named concept album to be his finest work. In August 1955, he would grace the cover of Time magazine, boosted by songs like "Young at Heart" and "Learnin' the Blues," and movies like "The Tender Trap" and "Guys and Dolls." "I feel eight feet tall," he told Time.

Even as the Time story appeared, FBI field offices in Los Angeles, New York, Newark, Philadelphia, Chicago, Detroit, Albany and Salt Lake City were searching their files for "subversive information" on Sinatra. The Philadelphia office, for example, was asked to recontact the informant from 10 years ago who had first identified Sinatra as a Communist.

The effort went for naught. In a letter to the Justice Department dated December 27, 1955, Hoover singled out only Sinatra's position as vice chairman of the Independent Citizens Committee of the Arts, Sciences and Professions, a group labeled as a Communist front by the California Committee on Un-American Activities.

Hoover's letter bore an internal note referring to "nonspecific associations" of Sinatra's name with the Communist Party, but the note added that the "investigation failed to substantiate any such allegations."

Sinatra's days as a subversive threat were over.

The files covering the late '50s thin out and lose their urgency. They record sightings of Sinatra with such gangsters as Joe Fischetti and Sam "Momo" Giancana, the boss of the Chicago mob. They quote an FBI informant as saying that Sinatra, for his part, had "a hoodlum complex." But by the late 1950s, Sinatra's standing was such that mob associations could no longer derail his career.

Then on March 22, 1960, an informant advised the bureau that Confidential magazine was investigating a rumor of "an indiscreet party" at Sinatra's Palm Springs home attended by Sen. John F. Kennedy and actor Peter Lawford, a Kennedy brother-in-law. The senator was campaigning hard for the presidency. Sinatra's "High Hopes" was his campaign's theme song. Gangsters were one thing; a potential president of the United States was another.

• • •

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.

• • •

On November 22, 1963, when JFK was assassinated in Dallas, Sinatra was in a Chicago cemetery, filming a scene for "Robin and the Seven Hoods." Two weeks later, Frank Sinatra Jr., who was then 19 years old, was kidnapped.

On December 8, 1963, Joe Amsler, a 23-year-old former high school classmate and friend of the singer's daughter Nancy, joined Barry Keenan, 23, and John Irwin, 42, in abducting Frank Jr. from his hotel room in Lake Tahoe.

The next night, a stricken Sinatra and Mickey Rudin met with four FBI agents, including Dean Elson, the FBI's special agent in charge of Nevada. Robert Kennedy called, promising help. Sam Giancana also called. ("Please," Sinatra told Momo, according to J. Randy Taraborrelli's Sinatra: A Complete Life, "let the FBI handle this.")

Two days later, Sinatra and an FBI agent delivered $239,985 to the kidnappers in Los Angeles. Frank Jr. was returned unharmed, and the kidnappers were arrested within three days.

After a highly publicized trial two months later in which defense lawyers accused Frank Jr. of perpetrating a hoax, Amsler and Keenan were sentenced to life in prison and Irwin to 16 years. All three were sent to the Medical Center for Federal Prisoners in Springfield, Mo., for psychiatric observation. Keenan ended up spending 4½ years in prison; Amsler and Irwin were released after 3½ years.

The kidnapping signaled a fundamental change in the FBI's relationship with Frank Sr. FBI agents worked closely with Sinatra and felt they knew him. On April 17, 1964, an FBI memo noted that Elson now had a "close personal relationship" with Sinatra. "Elson believes his relationship with Sinatra is so close that he might be able to induce Sinatra to cooperate with us."

The proposal was kicked up the FBI chain of command.

"I don't think the leopard will change his spots, but I recommend SAC Elson try his hand at this," wrote A.H. Belmont, one of Hoover's top assistants.

"I do not agree," wrote Tolson.

"I share Tolson's views," wrote Hoover.

It died there.

• • •

A two-page, single-spaced letter dated June 27, 1964, was sent to the house of Frank Jr.'s mother from the prison in Springfield. It was written by the Rev. Roger Schmit, the prison's Catholic chaplain.

"Dear Mr. & Mrs. Sinatra," it began. "I have become very well acquainted personally with Mr. Barry Keenan and Mr. Joe Amsler. I have spoken with both of these men on numerous occasions about the true Catholic approach to the crime of kidnapping your son."

The priest noted that he was "not speaking officially," but said it was evident that "Barry and Joe" were basically "good men." He was convinced that they would try to make amends to the Sinatras.

"No doubt you did experience a great deal of suffering and emotional anxiety during the kidnapping as well as perhaps some embarrassment during the trial. This is very understandable and for having caused you this suffering and embarrassment, Barry and Joe have often expressed their sorrow and regret."

The priest said the kidnapping had brought the kidnappers closer to God. He said that "if they are treated correctly," events would continue to spark a resurgence of religious fervor within them.

He closed with a sentiment that the Frank Sinatra of the 1940s might have embraced. "Many of the men here are not bad men, but they are persons who have made mistakes in life," Schmit wrote. "We ask God to forgive us our sins but we ask him to forgive our sins as we forgive the sins of our brothers."

A month later, Sinatra responded with five single-spaced pages of his own. He wrote in a cold fury. There is no other document like it in the files.

"Dear Father Schmit," he began. "Mrs. Sinatra and I were disturbed by your letter of June 27, 1964, written on behalf of Barry Keenan and Joseph Amsler.

"Since you have had no prior relationship to the Sinatra family, we assume that it was not the purpose of your letter to give us religious guidance. Accordingly, there could only be two possible purposes for your letter: (1) a request that we forgive Keenan and Amsler, and/or (2) that we take some action to express our forgiveness in order to alleviate the punishment the court has imposed on them."

Sinatra called the priest "presumptuous." He said the priest was wrongly casting the trial as a personal vendetta between Frank Jr.'s parents and the kidnappers. He said he and his ex-wife wanted only "a fair and impartial trial, and that if found guilty, the punishment imposed upon them be an intelligent punishment. Fortunately, we live in a country that expends great sums of money to assure defendants of a fair and impartial trial."

He continued:

"From the time our son was kidnapped, we placed the entire problem in the hands of the United States Department of Justice and we were indeed thankful that the Department, through the Federal Bureau of Investigation, was able to return our son to us unharmed."

Then Sinatra went on for two pages, saying he "must resent" the priest's implication that they should forgive the kidnappers. "It requires more than expressions of regret to a Chaplain or to others at your Medical Center to atone for sins."

Three days later, he sent the priest's letter and his reply on to a man who he felt would appreciate them.

"Dear Edgar," Sinatra wrote. "I am not sending you this correspondence for any official action, but thought you would find the correspondence interesting, particularly insofar as if reflects my own attitude with respect to what has happened.

"I would like to express my deep appreciation and thanks for the excellent work of the FBI in securing the safe return of my son, in solving the crime, and for the tremendous amount of work I know they did in assisting the Department of Justice in prosecuting the crime.

"Sincerely,

"Frank Sinatra."

Hoover wrote to Sinatra's Sunset Boulevard office a week later:

"Dear Frank,

"I can certainly understand your concern in this matter and appreciate your interest in sending me this correspondence. I also want to thank you for your very kind comments regarding our participation in the investigation relating to your son's kidnapping.

"As for my feelings in matters such as these, I think you would be interested in my introduction to the April, 1964, issue of the FBI Law Enforcement Bulletin wherein it was stated, 'In 1934, a New York City judge stated, "The demand of the hour in America is for jurors with conscience, judges with courage and prisons which are neither country clubs or health resorts. It is not the criminals, actual or potential, that need a neuropathic hospital," the judge added, "it is the people who slobber over them in an effort to find excuses for their crime." ' "

At the bottom of the copy of the letter, where Hoover would ordinarily scrawl his one-line comments, there was only an internal note, carefully typed:

"Bufiles reflect Father Roger Schmit, a 29-year-old Catholic priest, was a Departmental applicant in 1963 at which time no derogatory information was developed concerning him. The Director is well aware of the background of Sinatra."

• • •

After 1964, the FBI would still occasionally troll through the Sinatra files. The bureau would do "name checks" on him at the request of the White House or Scotland Yard, trotting out in a desultory fashion the old mob stuff. The memos started getting shorter, the information in them a bit shopworn.

The information the FBI now collected on Sinatra would mainly have to do with the crackpot threats against him.

By 1971, nine years after he had flown Sam Giancana in his private jet, Sinatra was using his Gulfstream II to ferry Martha Mitchell, wife of the U.S. attorney general, from San Francisco to Los Angeles.

The FBI noted that Sinatra "is becoming quite active" in President Richard Nixon's reelection campaign. By 1973, Sinatra was singing at the White House at Nixon's request. Sinatra chose to sing "The House I Live In," his 1945 paean to racial tolerance that made him the darling of the American left, to a man who got his first big boost in national politics from serving on the House Un-American Activities Committee.

The mob associations would continue to dog Sinatra, but the dogs would be agencies other than the FBI. In 1969, the New Jersey State Commission on Investigation had subpoenaed him to testify about organized crime and corruption in New Jersey. In 1972, the House Select Committee on Crime had subpoenaed him to testify about an old investment in a mob-controlled racetrack in Massachusetts. None of it fazed him.

In 1975, Judith Campbell Exner answered questions about JFK and Giancana in a closed session with staff members of the Senate Select Committee on Intelligence. Giancana was murdered the night before he was to talk to a lawyer for the committee. Sinatra was not subpoenaed.

In 1976, Sinatra had his picture taken backstage at a mob-controlled theater with Carlo Gambino, the New York boss of bosses. The habits of a lifetime proved hard to break, but Frank Sinatra was now beyond the reach of bad publicity.

In 1981, he appeared before the Nevada Gaming Control Board in a bid to win back the gaming license he had lost thanks to Giancana in 1963. One of Sinatra's character references was President Ronald Reagan, whose inaugural gala Sinatra had hosted the previous month.

As part of his reapplication, Sinatra obtained his FBI files under the Freedom of Information Act and gave them to the control board. Sinatra's lawyers described the file as 14 pounds and more than 1,000 pages of unsubstantiated complaints and anonymous letters. Investigators for the control board spent 13 months looking at the file and agreed.

With Mickey Rudin nearby, Sinatra testified for two hours, denying all the mob links, saying the wiseguys were mere acquaintances drawn by his celebrity. He said he socialized with them rarely, and never fronted for them in business.

When asked whether he carried $2 million in a briefcase to Lucky Luciano in Havana in 1947, Sinatra said: "Show me an attache case that can hold $2 million and you can have the $2 million."

The head of the control board had to smile at that. Sinatra received his license by a 4-1 vote. Even the person who voted against him said the mob allegations were groundless.

• • •

What began in hysteria ended in insanity.

The last entry in the Sinatra files is a letter postmarked March 7, 1985. It is handwritten and 19 pages long:

"Dear Sir:

"I am psychic and I must write to you about very serious problems.

"Frank Sinatra is the main problem."

The letter accused him of "trying to create a World War"; of trying to divide the country when he found such a war difficult to start; of "trying to instigate a black takeover"; of tampering "with television broadcasting, making people more prone to violence."

The letter blamed him for Amtrak accidents, plane crashes, poisoned Tylenol and "candy, around Halloween, being tampered with." And threats against Thatcher, and Brezhnev's death, and Andropov's, too, "which I really feel uncomfortable writing about because it involves another country, but I feel I must stress the seriousness of the problem with the mental degenerate named Frank Sinatra, which everyone seems to idolize. He is a maniac."

He controls Joey Buttafuoco, Burt Reynolds, Anne Murray, Robert Wagner and Barbara Mandrell.

He is responsible for the Kennedy curse: Joe, Jack and Bobby.

"I must kill him and since his family is not stopping him and also the fact that they would kill me for killing him – I must kill his family for the self defense of mine."

The FBI opened Bureau file #9-68981, UNSUB (for unknown subject) EXTORTION.

Agents tracked the letter-writer down in Newark, not far from where it began for Sinatra. When they interviewed her, she "advised that she has had numerous mental problems as a result of her divorce from her husband. [Redacted] acknowledged writing the letter and maintains that she is psychic. However, she concluded that she has no intentions of harming anyone."

An assistant U.S. attorney declined to prosecute.

"Newark [FBI] considers the captioned matter closed," reads the last line in Francis A. Sinatra's FBI files.

Jeff Leen is The Post's investigations editor.

© Copyright 1999 The Washington Post Company

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