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Authors: Tom Kuntz

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is aware of the fact that SINATRA enjoys surrounding himself with hoodlums and believes that SINATRA would give up his show business prominence to be a hoodlum himself if he had the courage to do so.

    
In 1959, an agent for the Internal Revenue Service questioned Sinatra under oath in Los Angeles during an investigation of possible mob skimming at clubs where Sinatra performed. In his testimony, Sinatra denied that the Chicago mob boss Sam Giancana was present at a string of nightly parties he threw that summer during an extended engagement at the Claridge Hotel in Atlantic City. But he did acknowledge recently becoming acquainted with the mobster. Sinatra’s friendship with Giancana would grow in the coming years and figured prominently in the singer’s life as he grew close to a rising young senator from Massachusetts, John F. Kennedy
.

    
Set out herein is the affidavit in question:

  • “Q. Are you acquainted with a Mr. Sam Giancana?

  • A. I am.

  • Q. How long have you known the gentleman?

  • A. A couple of years. A little under a couple of years.

  • Q. Approximately when did you first meet Mr. Giancana?

  • A. March 11, I think, 1958.

  • Q. Where did this meeting take place?

  • A. In the Fontainebleau Hotel.

  • Q. Miami Beach, Florida?

  • A. Yes.

  • Q. Have you ever had any business dealings with Mr. Giancana?

  • A. None.

  • Q. Has this relationship been strictly social?

  • A. Yes.

  • Q. Has Mr. Giancana ever approached you in connection with any financial business proposition?

  • A. No.

  • Q. When was the last time you saw Mr. Giancana?

  • A. Sometime early in August.

  • Q. 1959?

  • A. At the Chicago Airport, 1959.

  • Q. Mr. Sinatra, in regard to the previous interview which we had with you on November 6, 1959, at your attorney’s office, at that time you supplied information substantially as follows: That your relationship with Mr. Giancana was strictly friendly; that you had seen him approximately 6 to 10 times, several of these meetings having taken place at the Sands Hotel, Las Vegas, Nevada, where you were appearing at the time.

  • A. Yes.

  • Q. That you had considered Mr. Giancana more or less a fan of yours; that you possess no knowledge as to Mr. Giancana’s business activities; that you have never been approached by Mr. Giancana with a financial proposition. Is that correct?

  • A. That is absolutely correct.

  • Q. Do you have any way of knowing at this time how Mr. Giancana would have come into possession of your unpublished home phone number, CR 4-2368, listed to you at 2666 Bowmont Drive, Beverly Hills, California? Can you give us information as to how he may have come—

  • A. I gave it to him.

  • Q. Was there anything specific that you recall with reference to giving him this phone number?

  • A. Not at all. I give my phone number to many people.

  • Q. Would this likewise be true of your CRestview 5-4977, Oxford Publications, Inc., the unpublished number, TExas 0-8701, your unpublished phone at Metro Goldwyn Studios?

  • A. Yes.

  • Q. Was there any specific purpose that you had given these numbers to Mr. Giancana? A. None.

  • Q. Mr. Sinatra, information has come to our attention that during the period July 25, 1959 to August 2, 1959, you were staying at the Hotel Claridge, Atlantic City, New Jersey, and at that time you had rented numerous rooms at this hotel and had given a party which was attended by Mr. Giancana. Is that correct?

  • A. No.

  • Q. Were you staying at the Claridge at that time?

  • A. Yes.

  • Q. Has Mr. Giancana attended any parties given by you, Mr. Sinatra?

  • A. No.

  • Q. With reference to the last interview, at that time you supplied information that the occasion of your last meeting with Mr. Giancana was in Chicago and at that time you had contacted Mr. Giancana for the purpose of making arrangements to have him transfer your luggage from the airport to the train in Chicago. Is that correct?

  • A. I guess so, except one little thing. I don’t remember calling him because I don’t know where to call him. Apparently—I have to guess, but apparently he called me; that is probably what happened. I don’t remember calling him. I wouldn’t know where to call him.

  • Q. Have you ever had occasion to visit Mr. Giancana at his residence in Chicago?

  • A. No.

  • Q. Do you know where he lives?

  • A. No.”

    
Much later, the FBI would decide that Sinatra had probably made a false statement in the affidavit: An informant, a chorus-line dancer at the same party, apparently contradicted the singer’s account. The alleged lie would be discovered as the bureau closed in on Sinatra, aspirant to royal status in JFK’s Camelot
.

FIVE
SINATRA, THE KENNEDYS, AND THE MOB—THE COURTSHIP

“Some sort of indiscreet party.”

Sinatra met the actor Peter Lawford in April 1944, at a party given by the boss of MGM, Louis B. Mayer. Ten years later, Lawford married Patricia Kennedy, younger sister of John F. Kennedy. Sinatra’s friendship with Lawford blossomed into a friendship with Kennedy, whose stay at the singer’s home would later be memorialized by a bronze plaque on the door to its guest room.

By 1960, Sinatra and his Rat Pack colleagues had taken Las Vegas by storm, and the Massachusetts senator had become their golfing pal—and their candidate for president. On stage with Sinatra at the Sands one night, Dean Martin called the boyish politician in the audience “one of my best buddies”—and then cracked up the senator by turning to Sinatra and saying, “What the hell is his name?” All the while, mobsters like Chicago boss Sam “Momo” Giancana and Johnny Roselli lurked in the background, seeking to use Sinatra to gain political influence.

Memos about the overlapping exploits of Sinatra, Kennedy, and alleged mobsters soon swelled the FBI’s files.

    
The FBI first became interested in Sinatra’s friendship with Kennedy in early 1960 as the Massachusetts senator’s campaign was touring the country blaring its theme song—Sinatra’s specially reworked recording of “High Hopes.” On March 23, 1960, the special agent in charge (SAC) of the New Orleans FBI office gave Hoover an early indication of Sinatra’s role in the campaign and the mob’s interest in its outcome. It also provided evidence of Kennedy’s weakness for the ladies—including an as-yet-unidentified woman he met at the Sands in Las Vegas. She would become quite significant later
.

TO: DIRECTOR, FBI
FROM: SAC, NEW ORLEANS

SUBJECT: SENATOR JOHN F. KENNEDY
INFORMATION CONCERNING

    On 3/22/60,
who operates a
in New Orleans, La., furnished the following information:

stated that among
are JERRY WALD, Hollywood motion picture producer, and PHILLIP FRANK KASTEL, New Orleans top hoodlum.
stated that
KASTEL and other clients, he travels frequently to Las Vegas, Nev., Hollywood, and Miami, Florida. He said that
KASTEL’s
he has met a number of well known hoodlums, such as MEYER LANSKY, whom he described as a gambler operating in Miami and Havana, Cuba, and JOE FISCHETTI, aka. JOE FISH, who
believes is the dominant figure in the racketeering element in the Miami area.
claims that as a result of his contacts with these individuals, he has met socially a number of their associates, whose identities are not known to him, and whom he has not sought to identify, feeling that inquisitiveness on his part might be detrimental to his relationship with KASTEL.

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