Sinatra is photographed backstage with New York mobster Carlo Gambino.

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 Reagan is a character reference.

1983.

Receives Kennedy Center Honors Award for Lifetime Achievement.

1985.

January: Produces Ronald Reagan"s second inaugural.

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

May 23: Receives honorary degree from Stevens Inst.i.tute of Technology in Hoboken, N.J.

May 23: Awarded Medal of Freedom.

1988.

Goes 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 commemorate his seventy-fifth birthday.

1993.

October: Records the alb.u.m Duets Duets in collaboration with well-known vocalists who tape their parts separately, including Bono of the rock group U2. in collaboration with well-known vocalists who tape their parts separately, including Bono of the rock group U2.

1998.

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

Preface.

Numerous doc.u.ments on Frank Sinatra in the FBI files open with a short biography of the singer. Below is a typical one, from about 1950.

BIOGRAPHICAL DATA.

Francis Albert Sinatra, generally known as Frank Sinatra, was born December 12, 1915 or 1916, according to his Selective Service file, and on December 12, 1917, according to public source material. He was reportedly born in Hoboken, New Jersey, the son of Martin (also reported as Anthony) and Natalie Garavante Sinatra, 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 a Captain in the Hoboken Fire Department.

Sinatra received his public school education in Hoboken and left the Demarest High School in 1935 to work as a helper on a delivery truck for the Jersey Observer Jersey Observer and contrary to publicity reports, did not serve as a sports writer for this paper. He is also reported to have taken some engineering courses at the Stevens Inst.i.tute of Technology in Hoboken and in other reports is supposed to have attended the Drake Inst.i.tute, dates of attendance not given. and contrary to publicity reports, did not serve as a sports writer for this paper. He is also reported to have taken some engineering courses at the Stevens Inst.i.tute of Technology in Hoboken and in other reports is supposed to have attended the Drake Inst.i.tute, dates of attendance not given.

Sinatra started his singing career in 1935 after winning an amateur contest. He subsequently won a prize on the Major Bowes Amateur Hour and toured with a unit of this company for three months. By 1939 he was singing on eighteen sustaining programs on the radio, reportedly without financial remuneration. In June, 1939, he gave up his job with a New Jersey roadhouse, The Rustic Cabin, to appear with Harry James"s Band. About December, 1939, he joined Tommy Dorsey"s Band and stayed with him until the summer of 1942, when he returned to radio work and personal appearances. Sinatra was the singing star of the Lucky Strike Hit Parade radio program from February, 1943, to January, 1945. During this period he began his screen work and also appeared in the Wedgewood Room of the Waldorf-Astoria Hotel in New York City.

In addition to his work as a singer Sinatra was reported in 1946 to have an interest in a race track near Atlantic City, a band, a music publishing company, and one-third interest in the Barton Music Corporation and was then considering an interest in a sports arena to be built in Hollywood, a hotel in Las Vegas, and an office building in Beverly Hills.

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

Sinatra registered with Local Draft Board Number 19, Jersey City, New Jersey, and received a 4-F cla.s.sification on December 11, 1943.

Sinatra owned a home at 220 Lawrence Avenue, Hasbrouck Heights, New Jersey, until the spring of 1944 when he moved to Hollywood and bought a home there. He spends considerable time in New York City, but has no fixed address there.

Sinatra"s Selective Service file describes him as being 5"7," 119 pounds, slight build, dark brown hair, and blue eyes.

The files of the Identification Division also reflect that Sinatra was fingerprinted on October 6, 1943, by the War Department as a member of the USO Camp Shows, Incorporated, and that on January 30, 1947, he was fingerprinted by the Sheriff"s Office, Los Angeles, California, in connection with an application for a gun permit.

ONE.

SINATRA AND THE DRAFT.

"Bugle-deaf Frankie Boy"

During World War II, Frank Sinatra generated a lot of public resentment and complaints largely because his first peak of stardom-marked by tumultuous appearances at New York"s Paramount Theatre-had been made possible by his exemption from military service.

It turned out that the draft complaints weren"t so far-fetched: As FBI doc.u.ments in this chapter indicate, the young star had twice told the army he had no physical or mental disabilities, then later changed his story. His revised answer to draft doctors: He had suffered a perforated eardrum at birth and was "neurotic"-afraid of crowds in particular.

The ear ailment was bona fide, and Sinatra throughout his career demonstrated emotional instability. But this idol of millions of swooning teenaged girls, afraid of crowds? Could Sinatra have been pulling out all the stops to ensure a 4-F cla.s.sification?

The time was one of extreme patriotism and high paranoia, as demonstrated by the first complaint received by the FBI, the earliest doc.u.ment in the Sinatra files. The letter, received on August 13, 1943, was from a resident of San Jose, California, who had just heard a Sinatra radio broadcast. The FBI withheld the writer"s name.

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 ma.s.s-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. As you are well aware the future of some of these manufacturers is rather shaky unless something is done like that.

Sincerely, Hoover"s reply was perfunctory.

September 2, 1943 DearThis will acknowledge your recent communication.

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

Should you obtain any information which you believe to be of interest to this Bureau, please feel free to communicate directly with the Special Agent in charge of our San Francisco Field Division which is located at One Eleven Sutter Building, Room 1729, San Francisco, California.

Sincerely yours, John Edgar Hoover Director Complaints about Sinatra"s draft exemption soon attracted the FBI"s attention. One tip was pa.s.sed on by a man who couldn"t be ignored: the New York Mirror New York Mirror columnist Walter Winch.e.l.l, perhaps the most influential journalist of his day, and a very close friend of Hoover. An anonymous, typed letter to Winch.e.l.l prompted top FBI officials to order an investigation into Sinatra"s draft record in early 1944. The letter was dated just three weeks after Sinatra was cla.s.sified as 4-F (unacceptable for medical reasons) and only days after top draft officials questioned subordinates about the singer"s case columnist Walter Winch.e.l.l, perhaps the most influential journalist of his day, and a very close friend of Hoover. An anonymous, typed letter to Winch.e.l.l prompted top FBI officials to order an investigation into Sinatra"s draft record in early 1944. The letter was dated just three weeks after Sinatra was cla.s.sified as 4-F (unacceptable for medical reasons) and only days after top draft officials questioned subordinates about the singer"s case.

December 30, 1943 Mr. Walter Winch.e.l.l New York Mirror 235 East 45th Street New York, N.Y.

Dear Mr. Winch.e.l.l: 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 cla.s.sification. The money is supposed 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. MacArthur.

If there is any truth to these reports I think that it should be made known. Mothers around this section who have sons in the service are planning a pet.i.tion to Pres. Roosevelt asking for a re-examination of the singer by a neutral board of examiners. You"ll probably read about this in the papers within a few days unless you break the story first.

I wish I could give you my name but I would lose my job within 24 hours if I did. You"d probably recognize it immediately if I did because I have sent you numerous items in the past which appeared in your column.

In fact, the FBI had not been investigating Sinatra"s draft record. But the letter became a self-fulfilling prophecy. The resulting investigation prompted this memo several weeks later to a.s.sistant Director D. M. "Mickey" Ladd, head of the FBI"s Domestic Intelligence Division. The initial inquiry into Sinatra"s draft status was undertaken by the special agent in charge (SAC) for Newark, Sam K. McKee, who is reputed to have been one of the agents who gunned down Pretty Boy Floyd ten years earlier.

February 8, 1944 Call 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 above time and date I asked him whether or not he had heard any rumors to the effect that Frank Sinatra had paid $40,000 to obtain a 4-F cla.s.sification. Mr. McKee stated that he had heard nothing to this effect.

I asked SAC McKee to ascertain definitely whether Sinatra"s cla.s.sification was 4-F and if so, to determine why he received this cla.s.sification. However, I told him that it would not be necessary at this time to make a full scale investigation or to look into the charges of $40,000 being paid the examining doctors at Newark. McKee stated that he would do this immediately and advise the Bureau of the results.

Respectfully, G. C. Callan McKee informed headquarters of the results of his investigation several days later, first in a telephone call with one of Ladd"s underlings, Christopher Callan. McKee"s report was the first hint that Sinatra had given draft officials inconsistent statements about his medical condition. And the report was spiced up with a little s.e.x.

February 10, 1944

MEMORANDUM FOR MR. LADD.

Re: FRANK SINATRA Selective Service SAC McKee of the Newark Office advised that Sinatra"s cla.s.sification appeared to be regular and that he was disqualified because of a perforated ear drum and chronic mastoiditis and that his mental condition was one of emotional instability. McKee stated that in a prior physical examination in the fall of 1943 none of these defects were noted and that in a questionnaire dated December 17, 1940, in answer to a question as to his physical condition, Sinatra noted there were none to the best of his knowledge. He is cla.s.sified 4-F as of December 11, 1943.

McKee also said it had come to the attention of one of the Resident Agents at Hackensack, New Jersey, that Sinatra has an arrest record and that[image] Hackensack County Jail, who furnished this information, gave the Agent a photograph of Sinatra, arrest #42799. McKee advised that Sinatra was arrested in 1938 on a charge of seduction which was dismissed and he was later arrested on a charge of adultery. Hackensack County Jail, who furnished this information, gave the Agent a photograph of Sinatra, arrest #42799. McKee advised that Sinatra was arrested in 1938 on a charge of seduction which was dismissed and he was later arrested on a charge of adultery.

I instructed McKee not to take any further action in this matter. He said he would submit a letter today covering the above.

Respectfully, G. C. Callan A more detailed letter to Hoover disclosed that at Sinatra"s induction physical, he left the chief clerk of his local draft board in Hudson County, N.J., with the impression that he knew he"d be rejected. And it detailed how many times Sinatra had denied being emotionally unstable before claiming, in December 1943, that he was.

February 10, 1944 Director, FBI Re: FRANK ALBERT SINATRA SELECTIVE SERVICE.

Dear Sir: Reference is made to the telephone message from Mr. Christopher Callan at the Seat of Government on February 8, 1944 concerning the receipt by the Bureau of an anonymous letter alleging, in effect, that $40,000 had been paid to the doctors who examined FRANK ALBERT SINATRA and thereafter gave an opinion that SINATRA had a perforated eardrum and was unsuitable for military service.

In accordance with instructions, the investigation was limited to an examination of SINATRA"s Selective Service File in order to obtain from that file certain information as set forth below. On February 9, 1944, the file was examined by Special Agent[image] at Local Draft Board #19 for Hudson County, Room 308, 26 Journal Square, Jersey City, New Jersey. The Chief Clerk of this board is Mrs. MAE E. JONES. at Local Draft Board #19 for Hudson County, Room 308, 26 Journal Square, Jersey City, New Jersey. The Chief Clerk of this board is Mrs. MAE E. JONES.

(1) PRESENT CLa.s.sIFICATION: 4F as of December 11, 1943.(2) REASON FOR THAT CLa.s.sIFICATION: D.S.S. Form #221, "Report of Physical Examination and Induction," carries under Section 4, "Physical Examination Results," the following certification: "78. I certify that the above-named registrant was carefully examined, that the results of the examination have been correctly recorded in this form, that to the best of my knowledge and belief: ... (e) FRANK ALBERT SINATRA is physically and/or mentally disqualified for military service by reason of: 1. chronic perforation [left] tympanum; 2. chronic mastoiditis."This was supported by the stamped name, "J. WEINTROB, Captain, M.C., a.s.sistant Chief Medical Officer." Immediately following"79.... (b) FRANK ALBERT SINATRA was on this date rejected for service in the Army of the United States."This statement was supported by the typewritten name, "R. G. WALLS, Captain, Infantry." The certification and statement carried the place and date of Newark, New Jersey, December 9, 1943.

More detailed notations appeared in Section 4, "Physical Examination Results," as follows: "40. EAR, NOSE, THROAT ABNORMALITIES: Chronic perforation lt. drum. Hist of repeated discharge from ear-mastoid areas show coating in remaining cells and deformity of ca.n.a.l. Marks sclerosis in mastoid area...."50. MUSCOLOSKELETAL DEFECTS: Fracture deformity 3rd finger rt. N.D." N.D.""55. MENTAL: Emotional instability. N.D 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 file appeared to be in regular order. Mrs. Jones said that the Local Board had been particularly careful not to afford SINATRA special treatment and where any question of importance arose, the Board would immediately communicate with the State Headquarters for advice in view of the "position" held by SINATRA. Mrs. Jones also said that although it had been reported over the radio and otherwise that SINATRA had had a pre-induction physical examination and knew two weeks before the date set for his induction examination that he would be rejected, no such pre-induction examination was ever given by her board for any registrant. It had been the impression of Mrs. Jones that SINATRA had had the belief that he would be rejected inasmuch as he had continued to make plans for his new radio show, but she had readily explained that to herself through the thought that he had probably had his own physician examine him.

The following inconsistencies appeared in the file: In his Selective Service Questionnaire executed December 17, 1940, under series 2, "Physical Condition," SINATRA wrote in under "Have No"-"To the best of my knowledge, I have no physical or mental defects or diseases." In an undated Current Selective Service Questionnaire which was to be returned prior to November 7, 1941 and in answer to the question, "Do you have any physical or mental defects or diseases?," SINATRA wrote "No." On October 22, 1943, in the "Extract for D.S.S. Form #221-Report of Physical Examination and Induction," SINATRA answered Question #5, "What Physical or Mental Defects or Diseases Have You Had in the Past, if any?" by the one word, "No." In answer to Question #6, "Have you ever been treated at an inst.i.tution, sanitarium or asylum?" SINATRA wrote, "No." On October 22, 1943, Local Board Examining Physician A. 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 the attention of Special Agent[image] that FRANK SINATRA had a criminal record in Bergen County. From that FRANK SINATRA had a criminal record in Bergen County. From[image] Bergen County Jail, Hackensack, New Jersey, there was obtained an enclosed picture of FRANK SINATRA and the following information regarding the two occasions on which SINATRA was held in the Bergen County Jail: FRANK SINATRA, Arrest # 42799, Bergen County Sheriff"s Office, Hackensack, New Jersey was arrested on November 26, 1938 charged with Seduction. Disposition was marked, "Dismissed." FRANK SINATRA, Arrest #42977, was arrested on December 22, 1938, charged with Adultery. The disposition on this charge was not listed. Bergen County Jail, Hackensack, New Jersey, there was obtained an enclosed picture of FRANK SINATRA and the following information regarding the two occasions on which SINATRA was held in the Bergen County Jail: FRANK SINATRA, Arrest # 42799, Bergen County Sheriff"s Office, Hackensack, New Jersey was arrested on November 26, 1938 charged with Seduction. Disposition was marked, "Dismissed." FRANK SINATRA, Arrest #42977, was arrested on December 22, 1938, charged with Adultery. The disposition on this charge was not listed.[image] stated that the fingerprints taken at the time of the listed arrests were submitted to the Federal Bureau of Investigation, Washington, D.C. stated that the fingerprints taken at the time of the listed arrests were submitted to the Federal Bureau of Investigation, Washington, D.C.

The following description of SINATRA was obtained from the Selective Service File:

Name: FRANK ALBERT SINATRA FRANK ALBERT SINATRA.

Race: White White Age: 28 or 29 28 or 29 Date of birth: December 12, 1915 is listed in two forms; December 12, 1916, in one. December 12, 1915 is listed in two forms; December 12, 1916, in one.

Place of birth: Hoboken, New Jersey Hoboken, New Jersey Residence: 220 Lawrence Avenue, Hasbrouck Heights, New Jersey 220 Lawrence Avenue, Hasbrouck Heights, New Jersey Height: 5"7" 5"7"

Weight: 119 lbs. 119 lbs.

Build: Slight Slight Hair: Dark Brown Dark Brown Eyes: Blue Blue Complexion: Ruddy Ruddy Scars and Marks: Scar on left side of chin below mouth Scar on left side of chin below mouth Occupation: Vocalist Vocalist Education: 4 years high school, one year business school 4 years high school, one year business school Marital Status: Married 2-4-39, Jersey City, New Jersey Married 2-4-39, Jersey City, New Jersey Immediate relatives: Wife, Mrs. NANCY R. SINATRA, same address; Daughter, NANCY SANDRA SINATRA, born 6-8-40 (no record of second daughter appears in Selective Service File); Father, ANTHONY SINATRA, age 52, Hoboken, New Jersey; Mother, NATALIE SINATRA, age 49, Hoboken, New Jersey. Wife, Mrs. NANCY R. SINATRA, same address; Daughter, NANCY SANDRA SINATRA, born 6-8-40 (no record of second daughter appears in Selective Service File); Father, ANTHONY SINATRA, age 52, Hoboken, New Jersey; Mother, NATALIE SINATRA, age 49, Hoboken, New Jersey.

SocialSecurity#: 138-16-0442 138-16-0442.

Nationality: United States citizen ... United States citizen ...

This office has not received any rumors which would substantiate the allegations made in the anonymous letter.

Because of the limited investigation requested, no additional investigation is contemplated by this office.

Very truly yours, S. K. MCKEE.

SAC.

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