The Sinatra the Secret FBI Dossie - Tom Kuntz; Phil Kuntz - [PDF Document] (2024)

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Also by the Editors

The Titanic Disaster Hearingsedited by Tom Kuntz

The Starr Reportintroduction by Phil Kuntz TheStarr

Report: The Evidenceedited by Phil Kuntz

The Starr Evidenceedited by Phil Kuntz

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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

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CONTENTS

Introduction

The Life of Frank Sinatra: Selected Highlights

Editors’ Note

Preface

ONE: Sinatra and the Draft

TWO: Sinatra, the FBI, and the PressTHREE: Sinatra andCommunism

FOUR: Sinatra and the Mob—The Early Years

FIVE: Sinatra, the Kennedys, and the Mob—TheCourtship

SIX: Sinatra, the Kennedys, and the Mob—TheEstrangement

SEVEN: Sinatra Turns Right

EIGHT: The FBI and Sinatra the Man

Acknowledgments

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Introduction

When he died on May 14, 1998, Frank Sinatra was one of the mostchronicled celebrities ofmodern times—the focus of oceans ofink 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 uniquelypenetrating perspective, becamefully public only after his death:the Federal Bureau of Investigation’s extensive files on thesingerand screen star. Most were compiled over the course of severaldecades under the

watchful eyes of J. Edgar Hoover, as his agents investigatedwhether Sinatra was a draft-dodger, a Communist, or a front fororganized criminals.

Released in December 1998 in response to requests under theFreedom of Information Act,the 1,275-page dossier is a trove ofinsights into Sinatra’s life, his turbulent times, and, perhapsmostimportant, the Hoover-era FBI’s invasive and at times almostvoyeuristic ways.

Although Hoover’s FBI kept files on other celebrities, few wereas voluminous, for no othersubject was as enduring orcontroversial. For more than five decades, Sinatra was a majorforcein American society and popular culture, a politically active,hard-partying star who associatedwith powerful figures in both theunderworld and at the highest levels of government througheveryimportant turn in the latter half of the twentieth century. TheSinatra FBI files offerthemselves as an allegory of theAmerican Century and its obsessions.

Extensive excerpts from them are published here for the firsttime. Along with a limitednumber of historical documents from othersources, the files have been organized andsupplemented withexplanatory notes to put them in context and to highlight theirrevelations.

Taken together, they invite a reassessment of the entertainer.Revelations abound. chapter 1details how the rail-thin crooner withimpeccable phrasing at first told World War II draft boardofficialsthat he had no physical or mental disabilities, then asserted laternot only that he had a

perforated eardrum, which was true, but also an irrationalfear of crowds, which was highlydoubtful. With a blossoming careerat stake, could Sinatra have been feigning mental illness?chapter2 includes evidence suggesting an unholy alliance betweenpress muckrakers and theFBI’s star-obsessed top brass, whooccasionally helped favored journalists seeking dirt onSinatra.This new material lends credence to Sinatra’s lifelong grudgeagainst the press.

chapter 3offers a disturbing glimpse into the red-baiting1940s and 1950s, when Sinatra wasunjustifiably, in his words,“tagged [as a] commie.” Though for a time he stood byotherembattled Hollywood stars caught up in the paranoia, hebecame so sensitive to the charges that,according to anintermediary, he volunteered to become an undercover snitch in theFBI’s huntfor subversives. Hoover turned him down. So did the armyyears later, when Sinatra offered toentertain American troops inKorea.

In some key instances, what isn’t in the files is as importantas what is.

For example, although excerpts in chapter 4 and elsewhereassiduously note Sinatra’sinteractions with notorious hoodlums, theFBI gathered no evidence that mob pressure landedhim hisOscar-winning role as the pugnacious Private Angelo Maggio inFrom Here to Eternityin 1953. This canard is so embedded inthe popular imagination that it is assumed to be theinspiration fora scene in The Godfatherin which a severed horse’s headin a movie mogul’s

bed ensures a plum role for an Italian-American singer.Nor do the files support the widely heldassumption that the mob in1942 strong-armed Tommy Dorsey into releasing Sinatra fromacontract that entitled the bandleader to 43 percent of thesinger’s earnings for life.

More broadly, the files offer a striking case study of the wayHoover managed andmanipulated the sensitive information at hisdisposal. chapter 5, 6, and 7detail how the FBIdirector, withlittle subtlety, made sure each successive politician whobefriended the popularsinger knew exactly how much derogatoryinformation the FBI had on their friend.

John F. Kennedy’s recklessness is by now well documented, butthe files’ dry bureaucraticaccount of the president consorting withassociates of the very mobsters his brother the attorneygeneral wastrying to imprison will startle even the best-read Kennedyaficionados.

There also are moments of unintentional humor, as in the case ofthe straight-faced FBI

memo that says, “Sinatra denied he sympathized with Lenin andthe Marx brothers.” And thecapitalized names of Marilyn Monroe,Tony Bennett, and other celebrities leaven the G-men’s

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reports like the boldface type of gossip columns.

The files also shed light on the evolving nature of Sinatra’srelationship with the FBI: Heeventually joined with his would-bepursuers in the bureau in a mutually respectful commoncause, whenSinatra’s son was kidnapped in 1963.

In sum, the files track an iconic career whose arc seems topersonify postwar America’s lossof innocence: Sinatra’s evolutionfrom liberal, idealistic crooner to sophisticated,sexuallyliberated swinger to jaded Las Vegas headliner and friendof Republican presidents.

Was the scrutiny unfair?

The FBI twice seriously considered prosecuting Sinatra, once fordenying that he was aCommunist and once for denying that hepar-tied with a mobster. But despite coast-to-coastinvestigations,the FBI couldn’t make a case against him.

Sinatra’s problem throughout his career was that he never didmuch to remove the taint ofguilt by association, especiallywith the mob. Judged by the company he kept, Sinatra keptinvitingmore scrutiny. The FBI obliged, and its files grew until the singerbecame, as the

journalist Pete Hamill put it, “the most investigatedAmerican performer since John WilkesBooth.”

But in many ways Sinatra wasn’t so unique as a subject of FBIinterest. The agency kept fileson thousands of people, famous andotherwise, whenever they figured in investigations, nomatter howtangentially.

According to Hoover’s longtime deputy director, Cartha D. “Deke”DeLoach, the main FBIdossier on someone like Sinatra wouldn’t havebeen kept in the agency’s collection of “CentralFiles,” which wereopen to virtually anyone in the bureau. Instead, most of theSinatra material

would have ended up in the “Official and Confidential” files ofwell-known people, whichwere located in Hoover’s suite in two smallfiling cabinets behind the desk of his secretary,Helen Gandy.

There was nothing sinister in this, DeLoach maintains. In his1995 memoir, Hoover’s FBI:The Inside Story of Hoover’sTrusted Lieutenant, DeLoach writes: “The purpose of keepingtheO&C Files in an area of limited access was to protect theprivacy of those about whominformation had been gathered, not tomaintain secret records for the purpose of blackmail.”

Many a Hoover chronicler would disagree with DeLoach about thesanctity of his boss’smotives, but what is undeniable is that thedirector often took a personal interest in the minutiaeof Sinatra’slife. Readers of these pages can judge for themselves why.

The FBI began compiling the dossier during one of the mostcharged moments in American

history—the 1940s. From the start of the Second World War,Sinatra’s rise to fame stirred anincredible amount of resentmentand envy. The crooning heartthrob was thrilling millionsof

bobby-soxers, and making millions doing it, while avoidingthe fate of the hundreds ofthousands of other young men whoforwent love and fortune to fight European fascism andJapaneseimperialism.

As Sinatra himself noted, he was a surrogate to young women for“the boy in every cornerdrugstore who’d gone off, drafted tothe war.” The popular historian William Manchester put itanotherway: “I think Frank Sinatra was the most hated man of World WarII.”

And so, on the heels of pandemonium-filled appearances at NewYork’s Paramount Theatre,a letter arrived at FBI headquarters inWashington. Thus began the FBI’s shadow biography ofFrankSinatra on August 13, 1943: A concerned citizen intimated darklythat a “shrill whistlingsound” of shrieking bobby-soxers during arecent Sinatra radio broadcast might have been adevious technique“to create another Hitler here in America through the influence ofmass-hysteria!”

Later, an FBI memo said that the columnist Walter Winchell gavethe bureau a reader’s letterasserting that the FBI wasinvestigating whether the singer had bribed his way out of thedraft.The FBI wasn’t investigating any such thing, but the tipinsured that it would. In February 1944,the FBI opened a “limitedinquiry” that actually was far-reaching enough to dredge uprecordsof Sinatra’s 1938 arrest in New Jersey for an alleged“seduction” under a false promise ofmarriage—a charge thatwas later changed to “adultery” after it was discovered thatthesupposed victim was married. That matter also was dropped, andSinatra was free to love andleave again.

As World War II ended, Sinatra charmed his fans with songs like“Put Your Dreams Away”

and frothy films likeAnchors Aweigh, with Frank playingGene Kelly’s wide-eyed, sailor-suitedsidekick. But a serious film,all of ten minutes long, proved more important to the young

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promptly.”

Agents looked into the matter and later reported on a bizarremeeting in which Sinatra tried topersuade three army generalsto let him sing for the troops. One general congratulated Sinatraonhis fine performance inFrom Here to Eternity—a moviethat was probably more subversivethan Sinatra himself ever was, forit was about infidelity, indiscipline, and brutality inthemilitary. “I am just as communistic as the Pope,” Sinatra toldthe generals, to no avail.

Yet the FBI persisted in trying to dig up “subversiveinformation” on Sinatra as agents triedto prove that he lied indenying Communist affiliations to get a passport. Finally they gaveup,and Hoover concluded in a memo that despite repeated“nonspecific associations” of Sinatra’sname with the Communistparty, “the investigation failed to substantiate any suchallegation.”

Not that it mattered much. By the mid-1950s, Sinatra wasback on top. A collaboration at

Capitol Records with the arranger Nelson Riddle was yielding thebest work of Sinatra’s career,albums of swing and sophistication,includingIn the Wee Small Hours (1955) and SongsforSwingin’ Lovers (1956). He followed his Oscarsuccess with memorable roles in, among otherfilms,Suddenly (1954), in which he played a would-be presidentialassassin—an eerieforeshadowing of Jack Kennedy’s murder.

The FBI’s interest in Sinatra might have receded but for his mobassociations, which ifanything were growing. In 1954 he hadbought a 2 percent stake (later increased) in the SandsHotel in LasVegas, which reputedly had mob backers. He was seen with JoeFischetti, one ofthe mobsters he had accompanied to Havana,and was especially friendly with Sam “Momo”Giancana, the Chicagomob boss who had interests in many of the clubs where Sinatrahad

performed.

But what really got the FBI’s attention was his growingcloseness to the rising young senatorfrom Massachusetts whowas running for president. Senator John F. Kennedy had evenadoptedSinatra’s “High Hopes” as his 1960 campaign theme song. Sinatra,for his part, badlywanted a place in Camelot. After hiring Maltz,the screenwriter for The House I Live In, whowas now blacklisted,to do a script for another movie, Sinatra bowed to pressure fromtheKennedys, first by delaying the news until after the 1960 NewHampshire primary and then

jettisoning Maltz altogether.

Hoover received regular reports on all this and more. On March22, 1960, an informant toldthe FBI that Confidentialmagazine was investigating a rumor that Senator Kennedy hadattended“an indiscreet party” at Sinatra’s Palm Springs home. Later the FBInoted that Sinatraand Kennedy had partied together in New York,too, and that Confidential reportedly had“affidavitsfrom two mulatto prostitutes in New York.” In Las Vegas, the FBIheard that “show

girls from all over town were running in and out of thesenator’s suite” and that “Kennedy hadbeen compromised with awoman.”

According to FBI informers, the mob was looking for an in withthe next president of theUnited States. As one memo put it, the mobwanted Sinatra to use his show-biz friendship withKennedy in-lawPeter Lawford to get close to Jack Kennedy “so that Joe Fischettiand othernotorious hoodlums”—Sinatra’s pals—“could have anentrée to the Senator.”

After the mob reportedly helped Kennedy win the election, theFBI examined the phonerecords of one Judith Campbell and discoveredthat she was mixed up with both the presidentand Sam Giancana—notto mention Sinatra, who had introduced her to both men onseparateoccasions. It wasn’t hard to figure out that she was thepresident’s lover, as she lateracknowledged. 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-subtlesuggestion that the president’scoziness with Sinatra could destroyhis presidency.

JFK got the message. In March 1962, the president distancedhimself from Sinatra bycanceling a scheduled stay at the singer’sPalm Springs complex, staying instead at the nearbyhome of BingCrosby, a rival crooner and a Republican at that. It must havehurt: Sinatra’slong-cultivated friendship with JFK was over, andthe mob wasn’t happy. An FBI memo laternoted that “Chicagosources have advised of Giancana’s disappointment in Sinatra’sapparentinability to get the administration to tone down itsefforts in the anti-racketeering field.”

Not that Sinatra was through hanging around with toughguys. Far from it: He was sosuccessful now, having just started theReprise record label and flying in his own private jet,that hedidn’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

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Packers Dean Martin and Sammy Davis, Jr., at the grand reopeningin suburban Chicago of themob-run Villa Venice Supper Club.According to an FBI memo, the appearance by Sinatra’sclan was “whatcan only be termed a command performance” in return for past favorsfromGiancana. Onstage, Dean Martin even sang parody lyrics aboutnot getting paid for the gig.

Sinatra had the red-meat crowd roaring with a typically viciousputdown of the HearstBroadway columnist critical of his connectionto JFK: “I met many, many male finks but Inever met a female finkuntil I met Dorothy Kilgallen. I wouldn’t mind if she was agood-looking fink.”

Sinatra talked the hoodlum talk, but was he walking the walk?Many in Attorney GeneralRobert Kennedy’s anti-mob JusticeDepartment believed so. But hard evidence was elusive, asthe FBIfiles demonstrate.

On April 24, 1963, the special agent in charge of the FBI’s LosAngeles office asked Hooverto consider bugging Sinatra’s homein Palm Springs. Surprisingly, Hoover promptly denied therequest.“You are reminded that all misurs [microphone surveillances] mustbe completely

justified,” said the reply.

That summer, however, the FBI got a compelling new reason tokeep the heat on Sinatra. Atthe Cal-Neva Lodge in Lake Tahoe, acasino resort in which Sinatra held a major interest,Giancana hadbeen spotted ensconced with his girlfriend, the singer PhyllisMcGuire of theMcGuire Sisters. The resulting public furor—Giancanawas proscribed from the casino as aknown mobster—forced Sinatra torelinquish all his gambling interests in Nevada, at boththeCal-Neva and the Sands in Las Vegas.

Soon afterward, Dougald D. MacMillan, one of RFK’s top mobprosecutors, arrived in Los

Angeles with authority to “review all pertinent information inan effort to determine whetherprosecution could beinitiated against Sinatra.” But his Los Angeles colleagues scoffedat hisgrandstanding plan to start off by grilling top stars andSinatra friends like Dean Martin, SammyDavis, Jr., Dinah Shore, andEddie Fisher. “MacMillan is a boy on a man’s errand,” anFBIofficial scrawled on one memo. When Hoover found out aboutMacMillan’s plan, he called itoff.

Two months later, according to FBI memos, serious considerationwas given to prosecutingSinatra for denying in an interview withthe Internal Revenue Service that Giancana hadattended atwo-week-long party he threw at the Claridge Hotel in AtlanticCity. The FBI hadevidence that Sinatra was lying—the testimony of achorus girl at the party—but the matter wasdropped as an “apparent,though minor, violation of the law.” Sinatra would never haveacloser brush with the FBI.

At least not in the legal sense: On December 8, 1963, two weeksafter Kennedy’sassassination, Frank Sinatra, Jr., age nineteen, waskidnapped from his hotel room in LakeTahoe and held for ransom bythree men, one of them an ex-schoolmate of the singer’sdaughterNancy. Two days later, Sinatra paid nearly $240,000 to secure hisson’s release; theFBI arrested the three kidnappers days later.

The FBI agents who had worked closely with Sinatra throughoutthe ordeal felt they hadmade a breakthrough with the singer. One ofthem, Dean Elson, the bureau’s special agent incharge for Nevada,had developed a “close personal relationship” with the star andsuggestedthat he “might be able to induce Sinatra to help us,”according to a memo.

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

views.”Still, the kidnapping episode demonstrated that Hooverand Sinatra shared at least one thing

in common: an unforgiving attitude. When a Catholic prisonchaplain appealed for forgivenesson behalf of two of thekidnappers, Sinatra wrote back rejecting the suggestionas“presumptuous.” He informed Hoover of his exchange with thepriest in a “Dear Edgar” letter.In his “Dear Frank” reply, Hooverwas in an equally unmerciful mood, quoting a judge withapproval:“It is not the criminals … that need a neuropathic hospital; it isthe people whoslobber over them in an effort to find excuses forthe crime.”

Sinatra was entering a September of his years whose bitternessbelied the wistful tone of hissimilarly titled 1965 album. In 1966,according to an FBI memo, he hired a Washington publicrelations manto “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 theauthorities, “Sinatra is a verytemperamental, vindictive and moody individual and has periodswherehe dwells on his past life.”

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Within a few years of Hoover’s death in 1972, the FBI’s interestin Sinatra trailed off, andlittle new information was added to thefiles.

But in 1981, after a swing to the Republicans, a retirement, acomeback, and a fourthmarriage, Sinatra privately obtained his FBIdossier under the Freedom of Information Act. Heturned it over tothe Nevada Gaming Control Board as part of an effort to win backthegambling license he had lost thanks to Giancana in 1963.

Though the files offered plenty of reason to be suspicious ofSinatra, they proved noillegality. Perhaps that’s why Sinatra gothis license back. But it couldn’t have hurt that he onceagain hadfriends in high places: One of his character references wasPresident Ronald Reagan,whose inaugural gala the singer had hostedthe previous month.

To many, it looked like the fix was in. As with so much else inSinatra’s life, the episodedidn’t so much clear up doubts about hischaracter as illustrate them.

Less ambiguous was Sinatra’s statement to an interviewer in1963: “When I sing, I believe,I’m honest.”

The FBI files presented on the following pages do not refutethat.

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The Life of Frank Sinatra: Selected Highlights

1915

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

1935

September: As a member of the Hoboken Four, wins first prize onMajor Bowes and His

Original Amateur Hour.

1938

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

charged in Bergen County, N.J., with “seduction” under a falsepromise of marriage (andlater adultery, in the same case). Chargesare later dropped.

1939

February 4: Marries Nancy Barbato.

June: Joins Harry James and His Orchestra.

First recordings with the James band, including “All or Nothingat All.” James later releases

Sinatra from contract so he can join the Tommy Dorsey Band.

1940

January: Joins the Tommy Dorsey Band.

May 23: Records “I’ll Never Smile Again,” his first major hit,crystallizing the yearning anddespair of a generation torn apart byWorld War II.

June 8: Birth of first child, Nancy Sandra.

1941

Voted Outstanding Male VocalistbyBillboardandDownbeat.

First of nearly sixty film appearances:Las VegasNights.

1942

January: First solo recordings (with Axel Stordahl arranging) onRCA’s subsidiary labelBluebird, including “Night and Day.”

September: Last appearance with Dorsey band.

December 30: Appears at Paramount Theatre for the first time asan “extra added attraction”with Benny Goodman’s band.

1943

Lead singer on Your Hit Paraderadio show (until 1945).

June: First Columbia recording session, including “Close toYou.” Sinatra is backed by avocal chorus because of a musicians’strike.

August 13: The FBI opens its first file on Sinatra, “for thepurpose of filing miscellaneousinformation” on the star.

1944

January 10: Birth of second child, Franklin Wayne Emmanuel.

February: The FBI opens a “limited inquiry” into whether Sinatrahad bribed his way out ofthe draft.

Spring: Moves family to California.

October: Columbus Day riot by fans at the Paramount.

1945

Signs with MGM and makesAnchors Aweigh.

Makes the film short The House I Live In, a plea for ethnic andreligious tolerance.

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December 12: The FBI begins tracking Sinatra’s alleged Communistties.

1946

Wins special Oscar for his role in The House I Live In.

1947

February 11: Flies to Havana with the Fischetti brothers of AlCapone’s Chicago gang andsocializes there with Lucky Luciano,father of the modern Mafia. Columnist Robert Ruark seesSinatra withmobsters in Havana and reports about it.

February: Soon thereafter, the FBI files begin to note Sinatra’smob affiliations.

April 8: Sinatra assaults a hostile columnist, Lee Mortimer,outside Ciro’s nightclub in

Hollywood.

1948

June 20: Birth of third child, Christina (Tina).

1950

May: Television debut on The Star-Spangled Revue.

September 7: According to an FBI memo, a Sinatra go-betweenconveys the singer’s offer tobecome an FBI informer.

October: First television series, The Frank Sinatra Show.

1951Divorces Nancy Barbato.

August: Columnist Lee Mortimer alleges that in 1947 Sinatradelivered $2 million in cash toLucky Luciano, a charge neverproven.

November 7: Marries Ava Gardner in Philadelphia.

1952

September: Final Columbia recording session.

1953

From Here to Eternity(wins Oscar for Best SupportingActor the following year).

Separates from Ava Gardner (and is later divorced).April: Signswith Capitol Records and begins collaboration with the arrangerNelson Riddle.

1954

“Young at Heart” (song).

Buys a 2 percent interest (later increased) in the Sands Hotelin Las Vegas.

Army denies clearance to Sinatra to entertain troops in Korea,citing alleged Communistaffiliations.

1955

The Man With the Golden Arm(Academy Award nomination forBest Actor).

Guys and Dolls(film).September: Plays the Stage Manager inTV production of Thornton Wilder’s Our Town ,which produced the hitsong “Love and Marriage.”

1957

Pal Joey(film).

The Joker Is Wild(film).

“All the Way” (song).

October: Second TV series, The Frank Sinatra Show.

1959

Wins Grammy Awards for Album of the Year (Come Dance With Me!)and Best Solo VocalPerformance.

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1960

Forms Reprise Records.

Ocean’s Eleven(first film with the Rat Pack).

February 7: Sinatra introduces Senator John F. Kennedy to aformer girlfriend, JudithCampbell, after a Rat Pack performance atthe Sands Hotel in Las Vegas. They soon begin anaffair.

March: Sinatra introduces Campbell to the mobster Sam Giancanaat the Fontainebleau inMiami Beach. She and Giancana later had anaffair.

March: FBI begins tracking Sinatra’s socializing with John F.Kennedy.

1961

First Reprise album:Ring-a-Ding-Ding.

January: Produces John F. Kennedy’s inaugural.

February: J. Edgar Hoover memo to Attorney General Robert F.Kennedy on Sinatra and themob.

1962

The Manchurian Candidate(film).

March: JFK changes arrangements for trip to Palm Springs,staying at Bing Crosby’s homerather than Sinatra’s.

November 26-December 2: The Rat Pack performs at themobrun Villa Venice in suburban

Chicago, in what the FBI calls a “command performance” for SamGiancana. 1963

January 16: The FBI interviews Sinatra about his request for aTeamsters loan to expand theCal-Neva Lodge in Lake Tahoe, a casinoin which he has a major interest.

April 24: An FBI agent proposes bugging Sinatra’s Palm Springshome. Hoover says no.

Fall: Sinatra gives up his Nevada gambling license and hisinterest in the Cal-Neva Lodgeafter the mobster Sam Giancana isseen at the casino.

November 22: JFK is assassinated.

December 8: Kidnapping of Frank Sinatra, Jr.

December 12: Frankie is released on his father’s birthday.

1964

June 27: A Catholic prison chaplain writes to Sinatra asking himto forgive his son’sconvicted kidnappers. A month later, Sinatraangrily rejects the priest’s suggestion as“presumptuous” andcorresponds with Hoover about the matter.

1965

November: Wins Grammy awards for Best Album of the Year(September of My Years)andBest Solo Vocal Performance (“ItWas a Very Good Year”).

November: TV special Sinatra: A Man and His Music, winsEmmy and Peabody awards.Laudatory CBS TV News special Sinatra: AnAmerican Original, hosted by Walter Cronkite.

Von Ryan’s Express(film).

1966

July 19: Marries Mia Farrow.

Wins Grammys for Album of the Year (Sinatra: A Man and HisMusic)and Record of theYear (“Strangers in the Night”).

“That’s Life” (song).

1967

“Something Stupid” (duet with daughter Nancy).

1968

Divorces Mia Farrow.

1969

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“My Way” (song).

January 24: Death of his father, Martin Sinatra.

A New Jersey commission subpoenas Sinatra to testify aboutorganized crime in the state.

1971

March: Announces retirement.

June 13: “Final” performance at Los Angeles Music Center.

1972

House panel subpoenas him to testify about an old investment ina mob-controlled racetrackin Massachusetts.

1973

Sinatra sings “The House I Live In” at the Nixon WhiteHouse.

November: Ends retirement with TV show and album: Ol’ BlueEyes Is Back.

1974

October: The Main Event tour (televised).

1975

June 19: Giancana is murdered the night before an interview withSenate staff membersabout the mob’s connections to the Kennedyadministration and plots on Fidel Castro.

1976

July 11: Marries Barbara Marx (divorced from Zeppo).

Sinatra is photographed backstage with New York mobster CarloGambino.

1977

January 6: Death of his mother, Dolly, in a plane crash.

1980

“New York, New York” (song).

1981

Nevada gambling license restored. President Ronald Reaganis a character reference.

1983

Receives Kennedy Center Honors Award for LifetimeAchievement.

1985

January: Produces Ronald Reagan’s second inaugural.

March: Last entry in Sinatra FBI files, a death threat from amentally disturbed woman.

May 23: Receives honorary degree from Stevens Institute ofTechnology in Hoboken, N.J.

May 23: Awarded Medal of Freedom.

1988Goes on The Ultimate Event tour with Sammy Davis,Jr., and Dean Martin (later replaced by

Liza Minnelli).

1990

Launches the Frank Sinatra Diamond Jubilee tour to commemoratehis seventy-fifth birthday.

1993

October: Records the albumDuetsin collaboration withwell-known vocalists who tape theirparts separately,including Bono of the rock group U2.

1998

May 14: Dies at the age of eighty-two.

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Editors’ Note

Most of the documents excerpted in this book were partly and insome cases extensivelycensored by the FBI, usually to comply withprivacy laws and protect investigative sources.Many documentscontained material that duplicated material elsewhere in thefiles.

For these reasons, the editors have taken some very limitedliberties in a few cases. Forexample, the editors at timescompiled portions from multiple similar memos into compositesthatcontain the most noteworthy paragraphs from each of the originals.In those cases, the

editors also excluded as much duplicative and less-noteworthymaterial as possible, but didn’tnote each and every deletion. Andthe transcripts of electronically monitored conversationshave beenedited for clarity. The editors have disclosed such techniqueswhere appropriate inthe explanatory material preceding eachexcerpt.

In most other cases, three asterisks ( ) denote the deletion ofwhole sections ofintervening text, while ellipses (…)indicate lesser deletions. Text blacked out (redacted) by theFBI isnoted with black bars ( ). Throughout, clearly extraneousmaterial—such as

page numbers, time-and-date stamps, numerical filereferences, letterheads, miscellaneousunimportant handwrittennotations, and memo-routing information—has been deleted withoutuseof the denotations mentioned above. Most errors in spelling andgrammar have beencorrected, too. Also, because of copyright issues,several letters from private citizens, including

Frank Sinatra, have been paraphrased with only limited excerpts,in compliance with legal fairuse restrictions.

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Preface

Numerous documents on Frank Sinatra in the FBI files openwith a short biography of thesinger. Below is a typical one,from about 1950.

BIOGRAPHICAL DATA

Francis Albert Sinatra, generally known as Frank Sinatra, wasborn December 12, 1915 or1916, according to his SelectiveService file, and on December 12, 1917, according to public

source material. He was reportedly born in Hoboken, New Jersey,the son of Martin (alsoreported as Anthony) and Natalie GaravanteSinatra, who were both born in Italy. His father has

been a professional bantam weight boxer, boilermaker,shipyard worker during World War I,and subsequently became aCaptain in the Hoboken Fire Department.

Sinatra received his public school education in Hoboken and leftthe Demarest High Schoolin 1935 to work as a helper on a deliverytruck for the Jersey Observerand contrary topublicityreports, did not serve as a sports writer for this paper.He is also reported to have taken someengineering courses at theStevens Institute of Technology in Hoboken and in other reportsissupposed to have attended the Drake Institute, dates ofattendance not given.

Sinatra started his singing career in 1935 after winning anamateur contest. He subsequentlywon a prize on the Major BowesAmateur Hour and toured with a unit of this company for

three months. By 1939 he was singing on eighteen sustainingprograms on the radio, reportedlywithout financial remuneration. InJune, 1939, he gave up his job with a New Jersey roadhouse,TheRustic Cabin, to appear with Harry James’s Band. About December,1939, he joinedTommy Dorsey’s Band and stayed with him until thesummer of 1942, when he returned toradio work and personalappearances. Sinatra was the singing star of the Lucky StrikeHitParade radio program from February, 1943, to January, 1945.During this period he began hisscreen work and also appeared in theWedgewood Room of the Waldorf-Astoria Hotel in NewYork City.

In addition to his work as a singer Sinatra was reported in 1946to have an interest in a racetrack near Atlantic City, a band, amusic publishing company, and one-third interest in theBarton MusicCorporation and was then considering an interest in a sports arenato be built inHollywood, a hotel in Las Vegas, and an officebuilding in Beverly Hills.

On February 4, 1939, he married Nancy Barbato at Jersey City,New Jersey, and they nowhave three children.

Sinatra registered with Local Draft Board Number 19, JerseyCity, New Jersey, and received a4-F classification on December 11,1943.

Sinatra owned a home at 220 Lawrence Avenue, Hasbrouck Heights,New Jersey, until thespring of 1944 when he moved to Hollywood andbought a home there. He spends considerabletime in New York City,but has no fixed address there.

Sinatra’s Selective Service file describes him as being 5’7½,”119 pounds, slight build, darkbrown hair, and blueeyes.

The files of the Identification Division also reflect thatSinatra was fingerprinted on October6, 1943, by the WarDepartment as a member of the USO Camp Shows, Incorporated, andthaton January 30, 1947, he was fingerprinted by the Sheriff’sOffice, Los Angeles, California, inconnection with an applicationfor a gun permit.

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ONE

SINATRA AND THE DRAFT

“Bugle-deaf Frankie Boy”

During World War II, Frank Sinatra generated a lot of publicresentment and complaints

largely because his first peak of stardom—marked by tumultuousappearances at New York’sParamount Theatre—had been made possibleby his exemption from military service.

It turned out that the draft complaints weren’t so far-fetched:As FBI documents in thischapter indicate, the young star had twicetold the army he had no physical or mentaldisabilities, then laterchanged his story. His revised answer to draft doctors: He hadsuffered a

perforated eardrum at birth and was “neurotic”—afraid ofcrowds in particular.

The ear ailment was bona fide, and Sinatra throughout his careerdemonstrated emotionalinstability. But this idol of millions ofswooning teenaged girls, afraid of crowds? Could Sinatrahave beenpulling out all the stops to ensure a 4-F classification?

The time was one of extreme patriotism and high paranoia, asdemonstrated by the firstcomplaint received by the FBI, theearliest document in the Sinatra files. The letter,received

on August 13, 1943, was from a resident of San Jose, California,who had just heard a Sinatraradio broadcast. The FBI withheld thewriter’s name.

Dear Sir:

The other day I turned on a Frank Sinatra program and I notedthe shrill whistling sound,created supposedly by a bunch of girlscheering. Last night as I heard Lucky Strike producemore of thissame hysteria I thought: how easy it would be for certain-mindedmanufacturers tocreate another Hitler here in America through theinfluence of mass-hysteria! I believe thatthose who are using thisshrill whistling sound are aware that it is similar to thatwhich

produced Hitler. That they intend to get a Hitler in byfirst planting in the minds of the peoplethat men like FrankSinatra are O.K. therefore this future Hitler will be O.K. As youare wellaware the future of some of these manufacturers is rathershaky unless something is done like

that.

Sincerely,

Hoover’s reply was perfunctory.

September 2, 1943

Dear

This will acknowledge your recent communication.

I have carefully noted the content of your letter and wish tothank you for volunteering your

comments and observations in this regard.Should you obtain anyinformation which you believe to be of interest to this Bureau,please

feel free to communicate directly with the Special Agent incharge of our San Francisco FieldDivision which is located at OneEleven Sutter Building, Room 1729, San Francisco, California.

Sincerely yours,

John Edgar Hoover

Director

Complaints about Sinatra’s draft exemption soon attractedthe FBI’s attention. One tipwas passed on by a man who couldn’t beignored: the New York Mirror columnist Walter

Winchell, perhaps the most influential journalist of his day,and a very close friend of Hoover.An anonymous, typed letterto Winchell prompted top FBI officials to order aninvestigation

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into Sinatra’s draft record in early 1944. The letter was datedjust three weeks after Sinatrawas classified as 4-F (unacceptablefor medical reasons) and only days after top draftofficialsquestioned subordinates about the singer’s case.

December 30, 1943

Mr. Walter WinchellNew York Mirror235 East 45thStreet

New York, N.Y.

Dear Mr. Winchell:

I don’t dare give you my name because of my job but hereis a bit of news you can checkwhich I think is FrontPage:

The Federal Bureau of Investigation is said to be investigatinga report that Frank Sinatrapaid $40,000.00 to the doctors whoexamined him in Newark recently and presented him with a4-Fclassification. The money is supposed to have been paid bySinatra’s Business Manager.One of the recipients is said to havetalked too loud about the gift in a beer joint recently and areportwas sent to the F.B.I.

A former School mate of Sinatra’s from Highland, N.J., saidrecently that Sinatra has nomore ear drum trouble than Gen.MacArthur.

If there is any truth to these reports I think that it should bemade known. Mothers aroundthis section who have sons in the serviceare planning a petition to Pres. Roosevelt asking for a

re-examination of the singer by a neutral board of examiners.You’ll probably read about this inthe papers within a few daysunless you break the story first.

I wish I could give you my name but I would lose my job within24 hours if I did. You’dprobably recognize it immediately ifI did because I have sent you numerous items in the pastwhichappeared in your column.

In fact, the FBI had not been investigatingSinatra’s draft record. But the letter becameaself-fulfilling prophecy. The resulting investigationprompted this memo several weeks later toAssistant DirectorD. M. “Mickey” Ladd, head of the FBI’s Domestic IntelligenceDivision.The initial inquiry into Sinatra’s draft status wasundertaken by the special agent in charge(SAC) for Newark, Sam K.McKee, who is reputed to have been one of the agents whogunneddown Pretty Boy Floyd ten years earlier.

February 8, 1944Call 3:10 PM.

Transcribed— 3:25 PM.

MEMORANDUM FOR MR. LADD

RE: FRANK SINATRA SELECTIVE SERVICE

When SAC, S. K. McKee of Newark called me at the abovetime and date I asked himwhether or not he had heard any rumors tothe effect that Frank Sinatra had paid $40,000 to

obtain a 4-F classification. Mr. McKee stated that he had heardnothing to this effect.

I asked SAC McKee to ascertain definitely whether Sinatra’sclassification was 4-F and if so,to determine why he received thisclassification. However, I told him that it would not benecessaryat this time to make a full scale investigation or to look into thecharges of $40,000

being paid the examining doctors at Newark. McKee statedthat he would do this immediatelyand advise the Bureau of theresults.

Respectfully,

G. C. Callan

McKee informed headquarters of the results of hisinvestigation several days later, first in atelephone call with oneof Ladd’s underlings, Christopher Callan. McKee’s report wasthe

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first hint that Sinatra had given draft officialsinconsistent statements about his medicalcondition. And thereport was spiced up with a little sex.

February 10, 1944

MEMORANDUM FOR MR. LADD

Re: FRANK SINATRA Selective Service

SAC McKee of the Newark Office advised that Sinatra’sclassification appeared to be regularand that he wasdisqualified because of a perforated ear drum and chronicmastoiditis and that

his mental condition was one of emotional instability. McKeestated that in a prior physicalexamination in the fall of 1943 noneof these defects were noted and that in a questionnairedatedDecember 17, 1940, in answer to a question as to his physicalcondition, Sinatra notedthere were none to the best of hisknowledge. He is classified 4-F as of December 11, 1943.

McKee also said it had come to the attention of one of theResident Agents at Hackensack,New Jersey, that Sinatra has anarrest record and that Hackensack County Jail, whofurnished thisinformation, gave the Agent a photograph of Sinatra, arrest #42799.McKeeadvised that Sinatra was arrested in 1938 on a charge ofseduction which was dismissed and hewas later arrested on a chargeof adultery.

I instructed McKee not to take any further action in thismatter. He said he would submit aletter today covering theabove.

Respectfully,

G. C. Callan

A more detailed letter to Hoover disclosed that atSinatra’s induction physical, he left thechief clerk of his localdraft board in Hudson County, N.J., with the impression that heknewhe’d be rejected. And it detailed how many times Sinatra haddenied being emotionallyunstable before claiming, in December 1943,that he was.

February 10, 1944

Director, FBI

Re: FRANK ALBERT SINATRASELECTIVE SERVICE

Dear Sir:

Reference is made to the telephone message from Mr.Christopher Callan at the Seat ofGovernment on February 8,1944 concerning the receipt by the Bureau of an anonymousletteralleging, in effect, that $40,000 had been paid to thedoctors who examined FRANK ALBERTSINATRA and thereafter gave anopinion that SINATRA had a perforated eardrum and wasunsuitable formilitary service.

In accordance with instructions, the investigation was limitedto an examination ofSINATRA’s Selective Service File in orderto obtain from that file certain information as set

forth below. On February 9, 1944, the file was examined bySpecial Agent at LocalDraft Board #19 for Hudson County, Room 308,26 Journal Square, Jersey City, New Jersey.The Chief Clerk of thisboard is Mrs. MAE E. JONES.

(1) PRESENT CLASSIFICATION: 4F as of December 11, 1943.

(2) REASON FOR THAT CLASSIFICATION: D.S.S. Form #221, “Report ofPhysicalExamination and Induction,” carries under Section 4,“Physical Examination Results,” thefollowing certification: “78. Icertify that the above-named registrant was carefully examined,thatthe results of the examination have been correctly recorded in thisform, that to the bestof my knowledge and belief: … (e) FRANKALBERT SINATRA is physically and/ormentally disqualified formilitary service by reason of: 1. chronic perforation [left]

tympanum; 2. chronic mastoiditis.”

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This was supported by the stamped name, “J. WEINTROB, Captain,M.C., Assistant ChiefMedical Officer.” Immediatelyfollowing

“79…. (b) FRANK ALBERT SINATRA was on this date rejected forservice in the Armyof the United States.”

This statement was supported by the typewritten name, “R. G.WALLS, Captain, Infantry.”The certification and statement carriedthe place and date of Newark, New Jersey,December 9, 1943.

More detailed notations appeared in Section 4, “PhysicalExamination Results,” as follows:

“40. EAR, NOSE, THROAT ABNORMALITIES: Chronic perforation lt.drum. Hist ofrepeated discharge from ear—mastoid areas showcoating in remaining cells and deformityof canal. Marks sclerosisin mastoid area….

“50. MUSCOLOSKELETAL DEFECTS: Fracture deformity 3rd fingerrt.N.D.”

“55. MENTAL: Emotional instability.N.D….

“64. HEIGHT: 67K inches….

“65. WEIGHT: 119 lbs….

“75. BLOOD PRESSURE: (a) Systolic: 122; (b) Diastolic: 78.”

(3) GENERAL APPEARANCE OF FILE, ETC.: On its face, the fileappeared to be in regular

order. Mrs. Jones said that the Local Board had beenparticularly careful not to affordSINATRA special treatment andwhere any question of importance arose, the Board wouldimmediatelycommunicate with the State Headquarters for advice in view of the“position”held by SINATRA. Mrs. Jones also said that although ithad been reported over the radio andotherwise that SINATRA had hada pre-induction physical examination and knew two weeks

before the date set for his induction examination that hewould be rejected, no such pre-induction examination was ever givenby her board for any registrant. It had been theimpression of Mrs.Jones that SINATRA had had the belief that he would berejectedinasmuch as he had continued to make plans for his newradio show, but she had readilyexplained that to herself throughthe thought that he had probably had his own physicianexaminehim.

The following inconsistencies appeared in the file: In hisSelective Service Questionnaireexecuted December 17, 1940, underseries 2, “Physical Condition,” SINATRA wrote in under“HaveNo”—“To the best of my knowledge, I have no physical or mentaldefects or diseases.”In an undated Current Selective ServiceQuestionnaire which was to be returned prior to

November 7, 1941 and in answer to the question, “Do youhave any physical or mental defectsor diseases?,” SINATRA wrote“No.” On October 22, 1943, in the “Extract for D.S.S.Form#221—Report of Physical Examination and Induction,” SINATRAanswered Question #5,“What Physical or Mental Defects or DiseasesHave You Had in the Past, if any?” by the oneword, “No.” In answerto Question #6, “Have you ever been treated at an institution,sanitariumor asylum?” SINATRA wrote, “No.” On October 22, 1943,Local Board Examining PhysicianA. POVALSKI, M.D., Jersey City,found that SINATRA had none of the defects set forth in

Parts 1 or 2 of the List of Defects (form #220).

Independently of this investigation, it had come to theattention of Special Agentthat FRANK SINATRA had a criminal recordin Bergen County. From BergenCounty Jail, Hackensack, New Jersey,there was obtained an enclosed picture of FRANKSINATRA andthe following information regarding the two occasions on whichSINATRA washeld in the Bergen County Jail: FRANK SINATRA, Arrest #42799, Bergen County Sheriff’sOffice, Hackensack, New Jersey wasarrested on November 26, 1938 charged with Seduction.Dispositionwas marked, “Dismissed.” FRANK SINATRA, Arrest #42977, was arrestedonDecember 22, 1938, charged with Adultery. The disposition on thischarge was not listed.

stated that the fingerprints taken at the time of the listedarrests were submitted tothe Federal Bureau of Investigation,Washington, D.C.

The following description of SINATRA was obtained from theSelective Service File:

Name: FRANK ALBERT SINATRA

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Director, FBI

RE: FRANK ALBERT SINATRASELECTIVE SERVICE

Dear Sir:

Mr. William Guthrie, Clerk of the Second CriminalJudicial District of the County of Bergen,County Court House,Hackensack, New Jersey, furnished Special Agent thefollowinginformation regarding SINATRA:

Under docket #15228 of that court in the STATE vs. FRANKSINATRA, SINATRA wascharged, on November 26, 1938, by N.J., withhaving committed the

following offense: “On the second and ninth days of November1938 at the Borough of Lodi …under the promise of marriage[SINATRA] did then and there have sexual intercourse with thesaidcomplainant, who was then and there a single female of good repute… contrary to and inviolation of the revised statute of 1937.” ThePeerless Casualty Company, 241 Main Street,Hackensack, N.J., wentbond for SINATRA in the amount of $1500. This complaintwaswithdrawn on December 7, 1938 because it was ascertained thatthe complainant was in factmarried. In place of that complaint andunder docket #15307, the STATE vs. FRANKSINATRA, a complaintwas filed on December 21, 1938 by N.J., chargingSINATRA withadultery in that he, “On the second and ninth days of November 1938… didthen and there commit adultery with the said complainant, amarried woman, the wife of

. SINATRA went bond for himself in the amount of $500. OnJanuary 4, 1939, thecase was remanded to the Grand Jury by order ofJudge McINTYRE.

According to Mr. Guthrie, SINATRA’S attorney was Mr. HARRY L.TOWE of Rutherford,New Jersey, who at the present time is theCongressman (U.S. House of Representatives) fromthe 7th District ofNew Jersey.

Under docket #18450 for the Prosecutor of the Pleas of BergenCounty, it appears that a no-bill was returned on January 17,1939 by the Grand Jury in connection with the secondcomplaint. Inaccord with the no-bill the complaint was dismissed in open courtof QuarterSessions of Bergen County on January 24, 1939.

Because of the limited investigation requested, no additionalinvestigation is contemplated bythis office.

Very truly yours,

S. K. McKEESAC

Though there was no evidence to substantiate theallegation that Sinatra had paid $40,000to avoid the draft, therewere reasons to be suspicious. Spurred by Hoover’sinterest,headquarters ordered a more thorough investigation of thedraft-dodging allegation. Itturned out that details of thesinger’s emotional instability—including his supposed fearofcrowds—were omitted from the official reasons for his 4-Fclassification to “avoid undueunpleasantness for both the selecteeand the induction service.”

February 24, 1944

Director, FBI

Re: FRANK ALBERT SINATRASELECTIVE SERVICE

Dear Sir:

Reference is made to the two letters from this office,dated February 10, 1944 and February17, 1944, and to telephonemessage from Mr. CHRISTOPHER CALLAN on February 21, 1944.Inaccordance with instructions given by Mr. CALLAN, JOSEPH R.WEINTROB, Captain, U.S. Army Medical Corps, Chief Medical Officer,Armed Forces Induction Station, 113th InfantryArmory, Sussex Avenueand Jay Street, Newark 4, New Jersey, was interviewed bySpecial

Agent on February 23, 1944. The line officer in command of thisinduction station isCaptain RAYMOND E. WALLS. Captain WEINTROB’Ssuperior is Major FRANKGUIDOTTI, 39 Whitehall Street, NewYork, N.Y.

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SAC

After concluding that the original allegation wasunfounded, the matter was closed.Nevertheless, Sinatra laterwould take a beating on numerous fronts in the press . StarsandStripes, the military newspaper, called him a coward, and theconservative Hearst columnistWestbrook Pegler derided him as“bugle-deaf Frankie Boy Sinatra.” Nancy Sinatra insisted

years later in one of her books that after he’d beenrejected as unfit, her father “tried in vainto enlist for the nextseveral years.”

TO: Mr. D. M. LADD DATE: 2-26-44

FROM: Mr. G. C. CALLAN

USBJECT: FRANK ALBERT SINATRA

Selective Service

You will recall that we inquired into the SelectiveService status of Frank Sinatra because ofthe receipt fromWalter Winchell of an anonymous letter which he received allegingthat$40,000 had been paid by Sinatra to procure a 4-Fclassification. Newark found that Sinatrareceived a 4-Fclassification because of an ear ailment. It also discovered thatSinatra had beenarrested twice—once for seduction and once foradultery, both arrests resulting in dismissals,and both based onsame act.

The Director penned a notation on my memorandum to you datedFebruary 15, 1944, “Weshould be certain that there is nothingirregular in this case,” and upon your instructions, Icalled theNewark Office on February 21, 1944 at 4:45 p.m. and instructed ASAC[AssistantSpecial Agent in Charge] R. W. Bachman to have thephysician who examined Sinatra

interviewed. The Newark Office has complied with theseinstructions and there is attachedhereto Newark’s letter ofFebruary 24, 1944 which indicates very definitely that Sinatrawas

properly rejected because of a perforation of the membranatympani and acute or chronicmastoiditis. During the course of theinterview, it was ascertained from the examining

physician, Dr. Joseph R. Weintrob, Captain, U.S. Army,Medical Corps, that Sinatra stated hehad, in his early youth, beenoperated on on several occasions for mastoiditis. X-raypictureshave borne out Sinatra’s statements in this regard. CaptainWeintrob said the scar tissue whichwas the result of the operationwas readily perceptible and in this connection the operationalscarsvery clearly appear on the left profile photograph taken on theoccasion of one ofSinatra’s arrests by the Sheriff’s Officeat Hackensack, New Jersey. Either the perforation of thetympani orthe mastoid condition is, as Captain Weintrob points out, cause forrejection of aregistrant under War Department regulations.

It therefore appears that Sinatra was properly rejected frommilitary service and there is noindication that the statements madein the anonymous letter above referred to have anyfoundation.Consequently, in the absence of further instructions, no additionalinquiries will beconducted in this matter.

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TWO

SINATRA, THE FBI, AND THE PRESS

“Mr. Mortimer was appreciative.”

Frank Sinatra had a tempestuous and at times complicatedrelationship with both the FBI andthe press. Little did he knowthat the two institutions were sometimes collaborating witheach

other against him.They needed each other. As FBI agents delvedinto every aspect of the star’s life, they

depended on obvious sources of information like press reports aswell as confidentialinformants. The FBI files now make clear thatsome of the journalists who wrote those reportswere in effect FBIinformants as well, providing unsubstantiated rumors for the bureauto rundown—including Walter Winchell’s tip about the draft coveredin chapter 1. The FBI returnedthe favor on occasion, helpingjournalists digging for dirt on the singer.

In 1946, the ultraconservative Hoover demonstratedthat he was no fan of the singer whenLouis B. Nichols, one ofhis top aides, reported disapprovingly on a stop in thestar’snationwide tour, attaching a fairly innocuous press clippingas supporting material.

TO: Mr. Tolson DATE: May 14, 1946

FROM: L. B. Nichols

As a symptom of the state of mind of many young people Iwish to call to your attention thefollowing incident that occurredin Detroit on last Wednesday.

Frank Sinatra arrived in Detroit around midnight and a group ofbobby soxers were waitingfor him at the airfield. He eluded themand they then congregated at the stage door of theDowntown Theaterwhere he was scheduled to give his first performance around 10:00a.m. onThursday morning. The line started forming at around 2:00a.m. The police started challenginggirls who appeared to be under16 and tried to send them home. However, I have been told,there wasa long line of mere kids, many of whom carried their lunches, andthey remained inline until the theater opened. Truant Officersstarted checking the lines early in the morning and

were berated by the girls. There was widespread indignation onthe part of numerousindividuals that I came in contact with and asevere indictment of parents of the girls. Oneindividual went sofar as to state that Sinatra should be lynched. I am attachinghereto a pagefrom The Detroit Times showing some of the girls.

Handwritten notation by Hoover: Sinatra is asmuch to blame as are the moronic bobby-soxers. H.

A year later, Sinatra was taking a beating in thepress for his association with allegedmobsters, his draftrecord, and his political activities, which some consideredleft-leaningenough to be Communist.

Things boiled over at Ciro’s restaurant in Hollywood on April 8,1947 when he was

arrested for slugging his biggest press nemesis—the Hearstcolumnist Lee Mortimer. Thesinger later said the muckrakingscribe had been “needling me” for two years withblisteringcolumns. Nancy Sinatra has written that Mortimerheld a grudge against her father forrejecting a song he’dwritten.

Press clippings in the FBI files included speculation thata recent Mortimer piece aboutSinatra’s association with themobster Lucky Luciano had infuriated the singer. But onearticlepointedly noted that the Luciano story actually was broken byRobert Ruark, a “6-foot,200-pound columnist.” Mortimer weighedabout 120 at the time.

At Giro’s that night, Sinatra claimed Mortimer had goadedhim by calling him a “dago.”Mortimer insisted that Sinatra’s attackwas unprovoked. Sinatra later settled the case by

paying Mortimer $9,000 and withdrawing the sluraccusation.

Mortimer wasn’t through with Sinatra, though. A month after theGiro’s incident, the FBI’sNichols wrote this memo to Glyde A.Tolson, Hoover’s top aide and closest friend, to prepare

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the director for a planned meeting with the aggrieved columnist.This memo clearly showsthat the FBI was inclined to helpMortimer.

May 12, 1947

MEMORANDUM FOR MR. TOLSON

RE: FRANK SINATRA

In view of the Director’s conference with Lee Mortimer tomorrowit would appear that thereare three specific problems that havebeen raised on which the Director desires information.The followingis being submitted:

1. Mr. Mortimer said he had a picture of Sinatra getting off aplane in Havana with a tough-looking man whom he has been unable toidentify. He believes he is a gangster from Chicago.

Observation: It is suggested that this picture be exhibited toAgents who have worked on thereactivation of the Capone gang inChicago, as well as to Agents in the Newark Office whohave beenworking on criminal work, in view of the known contacts thatSinatra has had with

New York hoodlums. It is entirely possible that in thisway the unidentified picture might beidentified. If we identifiedthe individual we could secure a picture of the person identifiedandfurnish that to Mortimer and then in turn let him go out andverify the identification in such away as to remove the Bureau fromany responsibility of furnishing information.

2. Mortimer stated that Sinatra was backed when he first startedby a gangster in New Yorknamed Willie Moretti, now known asWillie Moore.

Observation: It is well known that Willie Moretti of HasbrouckHeights, New Jersey, controlsgambling in Bergen County, New Jersey,and is a close friend of Frank Costello. According toCaptainMatthew J. Donohue of the Bergen County Police, Moretti had afinancial interest inSinatra. In this connection, Sinatra residesin Hasbrouck Heights.

The Los Angeles Office has reported that a boxing show was beingsponsored by Sinatratogether with Henry Sanicola and Larry Rummans.According to reports, they incorporated,formed a company and soldstock to raise money to build “a little Madison Square GardenArena”in Los Angeles. At the same time it was reported that Sinatra wasinterested in

purchasing a hotel and gambling establishment that wasbeing built in Las Vegas, Nevada. Hewas assisted by an attorneynamed Herbert Pearlsen. Sanicola and Rummans were notfurtheridentified. It is known that Bugsy Siegel went to LosAngeles on December 18, 1946, to contact

Lana Turner, Jimmy Durante and Frank Sinatra for the purpose ofhaving them attend theopening of the Flamingo Hotel. Sinatra,however, did not attend either the opening onDecember 26, 1946, orDecember 28, 1946, which was attended by several starsincludingGeorge Raft, Brian Donlevy, June Haver, Lucille Ball,Sonny Tufts and others. It is likewiseknown that Mickey Cohen,well-known gambler and racketeer who operates out of LosAngeles,has been in contact with Sinatra on occasions.

In August, 1946, the New York Office was advised by FrancesDuffy, clerk of the LocalSelective Service Board #180, New YorkCity, that she resides at 424 Second Street, Brooklyn,

New York, in a home owned by Mrs. Mary Fischetti. MissDuffy stated that Sinatra,accompanied by Charles Fischetti, visitedthe home of his mother and spent the evening there inabout June of1946.

The Chicago Office advised that on August 8, 1946, a request wasmade of Charles Fischetti

to get in touch with his brother Joe for the purpose ofcontacting Frank Sinatra in New York toexpedite hotel reservationsaround November 7, 1946. It was indicated that the reservationsforthe hotel were desired by the Fischettis as they intendedto attend the Notre Dame-Armyfootball game. Fischetti is a Chicagohoodlum who was a subject in the Bureau’s investigationon theRe-Activation of the Capone Gang.

An informant in Chicago advised Joe Fischetti met Charles Baronandfurnished the information to the effect that both Joe Fischettiand Charles Baron had purchasedtwo dozen shirts and forwarded themto Frank Sinatra in Hollywood. The shirts were boxed intwo separateboxes and a card was placed in each box, one from Joe Fischetti andthe otherfrom Charles Baron. Baron apparently is associatedwith a Ford agency on South MichiganAvenue in Chicago.

The Washington News on April 10, 1947, carried a story datelinedHollywood, April 10,which carried the following statement:

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“Frankie explained he took out the permit two months ago to‘protect personal funds.’Shortly thereafter he went to Cuba, wherehe met Gambler Lucky Luciano. Their allegedfriendship was blisteredin Mr. Mortimer’s column and was believed to be the sparkforTuesday night’s fracas.

“(Frankie’s ‘friendship’ with Luciano was first revealed byRobert Ruark, 6-foot, 200-pound columnist for the News andother Scripps-Howard papers.)”

If Lee Mortimer has not already done so, he might contact RobertRuark. Ruark personallytold me that he has been investigatingSinatra and it is entirely possible that Ruark might haveuncoveredsome information that may be of assistance. There is attachedhereto Mr. Ruark’scolumn of February 20, 1947. Also, Mortimer mightcheck with law enforcement contacts inBergen County and endeavor tosecure the information from Captain Donohue which he has onMorettiand Sinatra.

3. Mortimer also desires Bureau information on Sinatra’s arreston a sex offense.

Observation: The records of the clerk of the Second CriminalJudicial District of the Countyof Bergen, Hackensack, New Jersey,reveal the following information: Docket 15228 in theState vs.Frank Sinatra reflects that Sinatra was charged on November 26,1938, by

New Jersey, as follows: “On the second and ninth days ofNovember, 1938… under the promise of marriage he (Sinatra) did thenand there have sexual intercourse withthe said complainant who wasthen and there a single female of good repute….” TheCharlesCasualty Company, 214 Maine Street, Hackensack, New Jersey,made Sinatra’s bond of $1,500.

On December 7, 1938, the complaint was withdrawn when it wasascertained that thecomplainant was in fact married.

Docket 15307 in the case of State vs. Frank Sinatra reveals acomplaint was filed onDecember 21, 1938, by New Jersey, chargingSinatra with adulteryin that he “… on the second and ninth days ofNovember, 1938 … committed adultery with thesaid complainant, amarried woman, wife of Sinatra made his own bond of $500 onJanuary4, 1939, and the case was remanded to the jury by order of JudgeMcIntyre.

Docket 18540 for the prosecutor of the bills, Bergen County,reveals that a no-bill wasreturned on January 17, 1939 by the grandjury and the complaint charging adultery wasdismissed in open courtfor quarter sessions on January 24, 1939. Sinatra was thenrepresented

by Harry L. Towe of Rutherford, New Jersey. Towe is now amember of Congress and theDirector may recall meeting him at myhouse prior to the Shrine Dinner in Alexandria.

4. Conceivably the New York Mirror might have access to therecords at Local Board #19 forHudson County, Room 308, 26Journal Square, Jersey City, New Jersey. In February of 1944,thechief clerk of this board was Mrs. Mae E. Jones. On the detailednotations appearing insection 4, physical examination results,(made by Captain J. Weintrob, M.C., Assistant ChiefMedicalOfficer), appears the following observation: “55—Mental: emotionalinstability, N.D.”When interviewed later, Captain Weintrobfurnished us with a copy of a communication whichhe had addressedto the commanding general wherein paragraph C reads as follows:

“During the psychiatric interview the patient stated that he was‘neurotic, afraid to be incrowds, afraid to go in elevator, makeshim feel that he would want to run when

surrounded by people. He had somatic ideas and headaches and hasbeen very nervous forfour or five years. Wakens tired in theA.M., is run down and undernourished.’ Theexamining psychiatristconcluded that this selectee suffered from psychoneurosis andwasnot acceptable material from the psychiatric viewpoint. Inasmuchas the selectee was to berejected on an organic basis, namely,

(1) Perforation of left tympanum

(2) Chronic mastoiditis, left,

the diagnosis of psychoneurosis, severe was not added to thelist. Notation of emotionalinstability was made instead. It wasfelt that this would avoid undue unpleasantness for

both the selectee and the induction service.”

There is attached hereto a more detailed summarymemorandum prepared in Mr. Rosen’sdivision on February 26.

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Tolson ended up meeting with Mortimer the following day.He later briefed Hoover on thevisit, all the while insisting thathe had not given thecolumnist any “official assistance,”whenin fact it appeared that he had been helpful.

TO: DIRECTOR DATE: May 13, 1947

FROM: CLYDE TOLSON

I talked this afternoon to Mr. Lee Mortimer, of the NewYork Daily Mirror, who wanted toask some questions concerning FrankSinatra. I told Mr. Mortimer that, of course, he realizedthat wecould not give him any official information or be identified inthis matter in anymanner, which he thoroughly understands.

He left a photograph taken of Frank Sinatra in Cuba and askedwhether we could identifyone individual shown in the picture.Copies of this photograph are being made and an effortwill be madeto determine whether any of our Agents are acquainted with theperson inquestion.

Secondly, he was interested in the association between Sinatraand Willie Moretti ofHasbrouck Heights, New Jersey. I toldMr. Mortimer in this connection that his best bet would

be to make appropriate contacts with the Bergen CountyPolice and possibly with a CaptainDonohue.

Also, Mr. Mortimer was interested in Sinatra’s arrest on a sexoffense. He had practically allof the information concerning thischarge and I merely indicated that he might secureinformation as tothe ultimate disposition of the charge by contacting the prosecutorof the bills,Bergen County, New Jersey.

Also, Mr. Mortimer had already learned of the contents of theselective service file pertainingto Sinatra and knew the locationof the board in Jersey City. He indicated that while he hadsecuredthe contents of this file on an informal basis, he understood thatthese records were notsubject to subpoena.

Mr. Mortimer had already contacted Robert Ruark, who has writtenseveral derogatoryarticles concerning Sinatra.

Mr. Mortimer told me that he understood that Colonel FainD’Orsey, alias Charles Conley,was arrested in the spring of 1946for smuggling narcotics from Mexico to the United States andat thetime of his arrest was driving a station wagon which belongs toSinatra. He indicated thatSinatra has made no effort to securerepossession of this station wagon but he has learned that

possibly D’Orsey will furnish enough information to theNarcotics Bureau to include Sinatra in

a conspiracy charge. He stated he planned to have the HearstOffice arrange for him to see Mr.Anslinger, of the NarcoticsBureau, in an effort to run this down. I am trying toascertainwhether we have a criminal record of this person on thebasis of the information furnished.

Mr. Mortimer was appreciative of the opportunity to talk to meand thoroughly understoodwe could not be of any official assistanceto him in this matter.

In an open letter to the public issued in thespring of 1947, Sinatra denounced “certainunscrupulousnewspapermen” who were attacking him and thanked the journalistsstandingby him, including Winchell, who had a role intouching off the Sinatra draft investigation in1944. And yearslater, Winchell evidently passed on another damaging andunsubstantiatedallegation to the FBI, as evidenced by thisexcerpt from a memo sent by the Los Angeles FBIoffice toHoover.

The Bureau by letter to Springfield dated July 11, 1951,captionedINFORMATION CONCERNING, furnished a photostatic copy of aletter written by

Peoria, Illinois, dated July 23, 1950, addressed to Mr. WALTERWINCHELL.A copy of this letter was confidentially furnished to theBureau. The letter contains quotationsfrom a booklet written byKENNETH GOFF entitled “Confessions of Stalin’s Agent.” Oneofthe quotations describes SINATRA as “one of the outstandingReds in Hollywood.” Accordingto letter, the booklet also includesother allegations concerning SINATRA.

Another reporter, Bill Davidson of Lookmagazine, asked the FBI for derogatoryinformation on Sinatra in1957. His January 20 letter to Louis Nichols, a Hoover aide,cited“constant allegations” circulating about Sinatra: HadSinatra been arrested for rape or

assault in Jersey City or Hoboken in the early 1930s? thejournalist wanted to know. Had hismother been arrested and chargedas an abortionist? And had two of Sinatra’s uncles been

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arrested for bootlegging during Prohibition?

In response, the FBI official immediately ordered up asynopsis of the Sinatra files (below)that included specific repliesto Davidson’s inquiries. Later that year, Davidson wroteanaward-winning series on Sinatra forLook magazine,prompting libel and invasion-of-privacylawsuits from the singer,which were eventually dropped.

TO: Mr. Nichols January 23, 1957

FROM: M. A. Jones

SUBJECT: FRANCIS ALBERT SINATRAAKA. FRANK SINATRA

SYNOPSIS:

Frank Sinatra was born December 12, 1915 or 1916, atHoboken, New Jersey, of Italian-bornparents. He left highschool in 1935 to obtain employment and during that year, beganhissinging career in night clubs and road houses in the northernNew Jersey area. He was marriedin 1939 to Nancy Barbato and hasthree children by that marriage. He divorced her in 1951 andmarriedactress Ava Gardner, from whom he was separated after approximatelytwo years ofmarriage. Allegations concerning his contactswith the Communist Party and numerouscommunist front groups came tothe Bureau’s attention for a number of years and wereincluded in amemorandum sent to the State Department in December, 1954, on theirrequestfor a name check on Sinatra. In view of a sworn affidavit,executed by him on January 10,1955, in connection with hisapplication for a passport, to the effect that he had never beenamember of the Communist Party or of any organization of asubversive character, the State

Department requested an investigation by the Bureau to determinewhether prosecution waswarranted against Sinatra for making a falsestatement in the application. The investigationdeveloped noevidence connecting Sinatra with the Communist Party or any of itsfront groupsaside from his membership in the Independent CitizensCommittee of the Arts, Sciences, andProfessions in 1946. Thisorganization was cited by the California Committee onUn-AmericanActivities as a communist front and included a number ofother prominent citizens in itsmembership. In 1948, Sinatraallegedly took part in an appeal to the voters of Italy tovoteagainst the communist ticket in the elections then being heldin that country. Material hasappeared in the press linking Sinatrawith known hoodlums, and in February, 1947, he wasalleged to havespent four days in the company of Lucky Luciano, the deportedItalian criminalwho was prominent in the narcotics traffic inAmerica. His name has also been prominentlylinked with Joseph andRocco Fischetti, members of the Capone gang, Willie Moretti,former

underworld boss of Bergen County, New Jersey, James Tarantino,an associate of Benjamin“Bugsy” Siegel, and other hoodlums on thewest coast. As recently as 1955, he was seenfrequenting anafter-hours bottle club in New York frequented by known hoodlumsand isreputedly one of the twelve major stockholders in the SandsHotel, a gambling establishment inLas Vegas allegedly controlled byAbner “Longy” Zwillman and Joseph Stacher, both notoriousgangstersfrom New Jersey…. Sinatra’s mother, Mrs. Natalie Sinatra, wasarrested in

November, 1937, on a charge of abortion. No disposition isgiven for this case. LawrenceGaravente, said to be an uncle ofSinatra. Bureaufiles do not verify his relationship to Sinatra. In1944, columnist Frederick C. Othman, in asyndicated article, quotedSinatra as saying that he received a letter from the Bureauconcerningan applicant in which he was requested to return fourautographed photographs for the girls inMr. Nichols’ office. Whencontacted, Sinatra denied the story but stated that he had receiveda

letter of that kind from the office of the Adjutant General andwould have Othman correct thematter. In September, 1950, through anintermediary, Sinatra offered his services to the Bureau,and theDirector noted his agreement with Mr. Tolson’s comment that we“want nothing to dowith him.”

* * *

SPECIFIC INQUIRIES MADE BY DAVIDSON

In his letter, Davidson stated that he planned on doing adefinitive, three-part profile onSinatra for “Look” magazine andwas concerned about several items which he had come acrosssince themanner in which they were resolved would help in “pitching” hisarticle….

Davidson asked for verification of the following:

1. That Sinatra was arrested for rape in Jersey City or Hobokenaround 1934. The charge issupposed to have been reduced toseduction and then thrown out by the Grand Jury.

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(Westbrook Pegler has reported this several times in hiscolumns.)

COMMENT: The records of the clerk of the Second CriminalJudicial District of thecounty of Bergen, Hackensack, New Jersey,reveal the following information: Docket15228 in the State vs.Frank Sinatra reflects that Sinatra was charged on November26,1938, by New Jersey, as follows: “On the second and ninth daysof

November, 1938, … under the promise of marriage, he(Sinatra) did then and there havesexual intercourse with the saidcomplainant who was then and there a single female ofgoodrepute….” The complaint was withdrawn when it was ascertained thatthecomplainant was in fact married. Docket 15307 in the case of theState vs. Frank Sinatra,indicates a complaint was filed on December21, 1938, by

New Jersey, charging Sinatra with adultery in that he “…on the second and ninth days ofNovember, 1938, …committed adultery with the said complainant, a married womanandwife of

Docket 18540, for the Prosecutor of Bills, Bergen County,reveals that no bill wasreturned on January 17, 1939, by the grandjury, and the complaint charging adultery wasdismissed in opencourt for quarter sessions on January 24, 1939….

2. That Sinatra was arrested and convicted of assault around thesame time (presumably the1930’s).

COMMENT: There is no information in Bufiles [bureau files] orthe records of theIdentification Division to substantiate such anarrest. News articles, however, reflect thatSinatra was arrested onApril 9, 1947, in Hollywood on a battery warrant based uponacomplaint by Lee Mortimer, New York columnist. Sinatra entered aplea of not guilty andwas released on a $500 bail. No dispositionof this case appears in the file.

3. That Mrs. Natalie Sinatra, his mother, was arrested 6 or 7times for operating an abortionmill in Hoboken between the years1930 and 1950 and that she might have been convicted once.

COMMENT: “Time” magazine, … a copy of which is attached,reported that Sinatra’s

mother, known generally as Dolly Sinatra, started out as apractical nurse and helped herhusband run a little barroom atthe corner of Jefferson and Fourth in Hoboken. Sheallegedly wasactive in Democratic ward politics and acted as a midwife at anumber ofneighborhood births. According to the article, shewas a “power” in her part of town, andin 1909 was made a districtleader. In 1926, the Mayor of Hoboken appointed her husbandto acaptaincy in the fire department. The records of the IdentificationDivision contain asingle card reflecting a criminal arrest onNovember 15, 1937, of Mrs. Natalie Sinatra, withalias DollySinatra, on a charge of abortion. Her residence was given as 841Garden Street,Hoboken, New Jersey, and the card was received fromthe Hoboken, New Jersey, PoliceDepartment. No disposition of thecase is given, and the incident is not mentioned inBufiles….

4. That Sinatra’s uncles, Champ and Lawrence Garavente, werearrested and perhapsconvicted of bootlegging in Hoboken in the1920’s and early 1930’s.

COMMENT: There are no references in Bufiles or the records ofthe IdentificationDivision identical with Champ Garavente. There isno information in Bufiles to the effectthat Lawrence Garavente isrelated to Frank Sinatra.

Not all journalists were treated well by the FBI. In thisexcerpt from a heavily censored

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memo dated September 17, 1963, the Los Angeles office reports tothe director on informationprovided by a “sensationalist”journalist, whose name the FBI blotted out. The memorecountsthreats the journalist received that invoked the name of thereputed mobster SamGiancana, a Sinatra friend. The journalist alsomentions an encounter he’d had with Sinatraat the restaurant thesinger owned in Beverly Hills with the actor Peter Lawford,Jack

Kennedy’s brother-in-law, and other investors.

said that SINATRA does not like him as he had written upsome articlesunfavorable to SINATRA several years ago at a timewhen SINATRA was a part owner ofPuccini’s Restaurant. statedhe had a date one night and his girl friend insisted ongoing toPuccini’s and he finally agreed to reluctantly. While was at therestaurantSINATRA came in and surveyed the customers and thereafterwas paged to thetelephone. When he answered the telephone it wasdead and as he hung it up SINATRAappeared and called him all kindsof dirty names.

told SINATRA in effect, “I am not going to hit you since Isee you have a numberof your hoodlum friends around you. Giveme my check and I will get out of here.” SINATRAallegedly replied,“I don’t want your money … it is dirty money.”

Three years later, the same journalist contacted the FBIagain, as recounted here in anexcerpt from a heavily censoredTeletype.

TELETYPE

FBI LOS ANG.

7:07 PM PDST URGENT 5/9/66TO: DIRECTOR

FROM: LOS ANGELES

INFORMATION CONCERNING

CAPTIONED INDIVIDUAL TELEPHONICALLY CONTACTED THE OFFICE ATELEVENTHIRTY A.M. THIS DATE AND ADVISED THAT HE HAD BEEN BEATEN BYFOURINDIVIDUALS WHOM HE SUSPECTS AS BEING FRANK SINATRA’SMOB. HEREQUESTED FBI ASSISTANCE IN IDENTIFYING THESEINDIVIDUALS.

RELATED TO SINATRA’S DIFFICULTIES WITHMEXICANAUTHORITIES. WENT ON TO STATE THAT ONWHEN HE DROVE HIS CAR HE WASGRABBED BY FOUR THUGS AS HELEFT THE CAR AND WAS SEVERELY BEATEN. HESAID HE IMMEDIATELY NOTIFIEDTHE HOLLYWOOD DIVISION OF THE LOSANGELES PD WHO IS INVESTIGATING.

HE SAID HE IS CERTAIN IN HIS OWN MIND THAT THE FOUR THUGSWHOCOMMITTED THE BEATING WERE MEMBERS OF SINATRA’S GROUP. HE SAIDHEBELIEVES THIS SINCE SINATRA THREATENED HIM IN THE PAST

IT IS NOTED IN LOS ANGELES FILES THAT BY LETTER DATEDSEPTEMBERSEVENTEEN, NINETEEN SIXTY-THREE, THE BUREAU WASADVISED OF A CONTACTWITH AT WHICH TIME HE SPOKE OF AN ALLEGEDTHREAT MADE

BY SINATRA WHILE WAS DINING AT PUCCINI’S RESTAURANT, OFWHICHSINATRA IS REPORTEDLY PART OWNER.

REQUESTED THAT THE FBI IMMEDIATELY MAKE AVAILABLE TOHIMPHOTOGRAPHS OF SINATRA’S HOODLUM ASSOCIATES SO THAT HE, ,MIGHTVIEW THEM IN AN EFFORT TO IDENTIFY THE INDIVIDUALS WHO BEATHIM.

WAS TACTFULLY ADVISED THAT THIS WAS NOT A MATTER WITHINTHEINVESTIGATIVE JURISDICTION OF THE FBI, AND THAT IT WAS PURELYAMATTER FOR LOCAL POLICE AUTHORITIES. AT THIS POINT BECAMEVERYARROGANT AND OBNOXIOUS AND DEMANDED THAT THE FBI ENTER HISCASE. ITSEEMED THAT WAS MAKING EVERY ATTEMPT TO STAMPEDETHE FBI INTO HISCASE.

AFTER CLEARLY POINTING OUT THE POSITION OF THE FBI IN A MATTERSUCHAS THIS, THAT WE WILL COOPERATE WITH LOCAL POLICE AUTHORITIESIN EVERYWAY POSSIBLE, THAT IT IS A MATTER FOR POLICE INVESTIGATIONTHE CALL

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WAS TERMINATED IN WHAT APPEARED TO BE A FRIENDLY TONE.

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THREE

SINATRA AND COMMUNISM

“Mrs. Roosevelt in pants”

For many years, the FBI was much more concerned with combatingthe then ominous-seeming threat of communism than with fightingorganized crime, the very existence of which

Hoover questioned until the late 1950s. From the dawn of thecold war, the FBI intensivelymonitored the domestic activities ofnot only the Communist party, but also groups deemed tooleft-wingby Senator Joseph McCarthy, the House Un-American ActivitiesCommittee (HUAC),and conservative Sinatra antagonists in the presslike Lee Mortimer and Westbrook Pegler.

Sinatra was among the first of many entertainment figures whosepatriotism was thrown intodoubt by the red-baiting of theanti-Communists. His ardently liberal New Deal politics,ofcourse, made him an obvious target. And Sinatra wasn’t shyabout collaborating withoutspoken leftists, including Albert Maltz,the screenwriter for Sinatra’s acclaimed pro-tolerancefilm shortThe House I Live In(1945). The film, which won him a specialAcademy Award,was a mixed blessing at cold war’s outset: It madehim a darling of the American left.

It is clear, however, that the FBI was overstating the casewhen, in internal reports from the

period, it referred to Sinatra as a “communistsympathizer” or a “CP fellow traveler.” In theend, it had nothingon him but the ordinary activities of a liberal celebrity.

Moreover, the singer was more nimble than Maitz and others whowere blacklisted; he at firstbelittled charges that he was aCommunist sympathizer, then confronted them head-on. And atonepoint an intermediary told the FBI that Sinatra was willing to spyon certain