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Authors: Tom Kuntz

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We have received information over an extended period of time from sources, who have furnished reliable information in the past and who have knowledge of general criminal activities in the United States, that Sinatra has been a close friend and associate of Samuel Giancana, a former chauffeur and bodyguard for Anthony Accardo, the acknowledged leader of the syndicate (La Cosa Nostra) in Chicago, Illinois, prior to 1956. Giancana, described as a cold, brutal killer, assumed leadership of the syndicate in Chicago in approximately 1956. Giancana has been a guest at various places owned or operated by Sinatra and at Sinatra’s home in Palm Springs, California. It has been reported that due to Sinatra’s close association with Giancana and other syndicate hoodlums he lost his license to operate gambling establishments in the State of Nevada.
As a result of this loss, Sinatra was reported to have sold his interest in the Sands Hotel, Las Vegas, Nevada, for $43,500 per point for a total of $391,000 and his entire interest in the Cal Neva Lodge at Lake Tahoe, Nevada….

In March, 1963, an informant who has furnished reliable information in the past advised that Sinatra and Dean Martin, well-known singer, were long-time friends of John Anthony Matassa. Matassa is a former member of the Chicago Police Department, who resigned many years ago after taking the Fifth Amendment before the McClellan Committee and as of 1963 was a business agent for a Chicago, Illinois, local of the Teamsters Union and reportedly a close associate of Samuel Giancana and other syndicate hoodlums.

In early 1964 another informant, who has furnished reliable information in the past regarding general criminal activities in the United States, indicated among other things that Paul “Skinny” D’Amato, operator of the 500 Club, Atlantic City, New Jersey, and a business partner with Sinatra in Nevada, was a hoodlum and a member of the La Cosa Nostra syndicate. The informant stated that although Sinatra was not a member of the syndicate, he was big enough and close enough to the organization to obtain any favors he desired.

    
In January 1967, Sinatra testified behind closed doors before a federal grand jury in Las Vegas looking into casinos allegedly controlled by the mob. That May the Italian-American Anti-Defamation League tapped Sinatra to head a nationwide effort to discourage the stereotyping of Italians as mobsters. The choice of an entertainer publicly known to associate with accused gangsters seemed odd to some. Still, the new group helped persuade the producers of
The Untouchables
television series to change some of its hoodlum characters’ surnames
.

And it managed to land Vice President Humphrey as a speaker. A Justice Department official requested and received the usual briefing materials on Sinatra, which included some new information. (The next year, Sinatra returned the favor: He endorsed Humphrey for president in the Democratic
primary over Robert Kennedy, who had quit the Justice Department in 1964 to become a senator from New York.)

TO: Mr. Gale
DATE: May 18, 1967
FROM: W. V. Cleveland

SUBJECT: PROPOSED SPEECH BY VICE PRESIDENT
HUMPHREY BEFORE AMERICAN ITALIAN ANTI-DEFAMATION LEAGUE, INC., NEW YORK CITY, MAY 20, 1967

    On the night of 5-17-67, Mr. John T. Duffner, Executive Assistant, Office of the Deputy Attorney General, telephonically requested name checks of the following: Frank Sinatra, Ross J. DiLorenzo and the American Italian Anti-Defamation League, Inc. Duffner stated he was requesting this information in connection with a proposed speech by the Vice President before the American Italian Anti-Defamation League, Inc., on May 20, 1967.

Frank Sinatra is well known for his hoodlum associations and, according to recent press reports, has been named National Chairman of the above-mentioned league. The Department has been previously furnished complete details on the background of Sinatra and his association with hoodlums. Ross J. DiLorenzo is the president of this league. With reference to this organization, recent newspaper publicity has criticized it for the appointment of Sinatra to a high position in this organization. In an article dated May 12, 1967, in the “New York Times,” former New York Police Officer Ralph Salerno took this organization to task for appointing Sinatra as National Chairman and indicated strongly that the Italian American community should face the facts that some 10,000 Italian wrongdoers were disgracing the 20 million law abiding Italian American citizens and that this organization should devote its activities to assisting law enforcement in cleaning up that element of Italian American communities which is in violation of law and order.

Among the directors of the American Italian Anti-Defamation
League, Inc., are listed Anthony Scotto and Dr. Mario Tagliagambe, concerning whom we have received allegations from confidential informants that they are reported members of La Cosa Nostra.

With specific reference to Ross J. DiLorenzo, he is the individual who, in a letter to the Bureau in March of this year, endeavored to imply that a Bureau television show defamed Italian Americans. In our reply, we set the record straight and pointed out to DiLorenzo that no such defamation occurred and, in fact, the principal character of the show in question was named Roland which is not an Italian name.

May 18, 1967

FRANK SINATRA

During the summer of 1964 an informant who has furnished reliable information in the past indicated that he had learned from one of the top hoodlums in the syndicate that on one occasion Sinatra owed the syndicate “a lot of money.” He also stated that although it was publicly reported that Sinatra divested himself of all financial interests in gambling establishments in Nevada, he had actually not “cut loose” from his night clubs but that the names were changed concerning reported ownership.

The May 4, 1967, issue of “The New York Times” newspaper, New York City, contained an article captioned “Sinatra to Head Antibias Group.” This article indicates in part Sinatra had been named National Chairman of the American Italian Anti-Defamation League. A copy of this article is enclosed.

The May 12, 1967, issue of “The New York Times” contained an article captioned “Sinatra Assailed as Ethnic Leader.” This article indicates in part that Ralph Salerno, a former member of the New York City Police Department’s Central Investigation Bureau, criticized the selection of Sinatra as National Chairman of the
American Italian Anti-Defamation League stating Sinatra’s friendship and association with identified members of the Mafia “hardly matches the image the league is seeking to project as representative of the 20 million Americans of Italian birth or ancestry.” A copy of this article is enclosed. Details concerning Sinatra previously furnished Department.

    
Three months later, White House aide Mildred Stegall again asked for and received an update on the Sinatra file from the FBI, as shown in this excerpt
.

August 21, 1967
BY LIAISON      

Mrs. Mildred Stegall
The White House
Washington, D.C.
Dear Mrs. Stegall:

    Reference is made to your request for a review of the information in FBI files subsequent to the previous name check which was made on November 20, 1964, regarding Frank Sinatra.

Our files reveal that Frank Sinatra continues to associate both socially and on a business basis with alleged members of La Cosa Nostra and other members of the hoodlum element in this country. Notable among such associates are Sam Giancana, Chicago, Illinois, who reportedly has been out of the country for the past year, and Joseph Fischetti, Miami, Florida.

    
Meanwhile, Sinatra kept showing up in reports about the FBI’s routine surveillance of mob figures and hangouts
.

TO: Director, FBI
FROM: SAC, Miami

SUBJECT: ELSUR [Electronic Surveillance]
FRANK SINATRA 4/18/68

    In connection with the Anti-Racketeering investigation of JOSEPH FISCHETTI, aka, Miami installed an eavesdropping device in Puccini’s Restaurant, 991 N.E. 79th St., Miami, Florida.

On 3/26/62, FRANK SINATRA and FISCHETTI came to Puccini’s Restaurant for dinner and parts of the conversation were overheard concerning his, SINATRA’s, returning to Los Angeles and the airport being “fogged in,” and they discussed the possibility of chartering a plane to New Orleans. It was general conversation and nothing was disseminated nor learned of value.

    
Later that year, Sinatra canceled campaign appearances on behalf of Humphrey, after
The Wall Street Journal
detailed his continuing mob associations. By 1969, Sinatra’s politics had begun to lean right. Shortly after Nixon’s inauguration, the FBI (presumably Hoover himself) wrote to Nixon’s top aide, John D. Ehrlichman of Watergate fame, to fill him in on Sinatra’s background
.

April 25, 1969

Honorable John D. Ehrlichman
Legal Counsel to the President
The White House
Washington, D.C.
Dear Mr. Ehrlichman:

    This letter is being written to you to outline briefly association for many years by Frank Sinatra with many leaders of La Cosa Nostra. As you know, that organization is the dominant force in the country’s organized crime underworld.

Sinatra, who was born December 12, 1915 (or 1916), in
Hoboken, New Jersey, was associated early in his singing career with the late notorious Willie Moretti, a long-time La Cosa Nostra leader in northern New Jersey who became the victim of a gangland type slaying in 1951. Also quite early in his career, Sinatra was quite friendly with Paul Emelio D’Amato, a La Cosa Nostra member who, for many years, was the proprietor of The 500 Club, a night spot in Atlantic City, New Jersey.

Sinatra’s association with D’Amato, who has served a penitentiary sentence as a panderer, continued over the years with Sinatra appearing at The 500 Club during many summer seasons. It has been reported that during some of those appearances, Sinatra rented one or two entire sleeping floors in the Claridge Hotel in Atlantic City for party purposes, the party actually being a cover for clandestine meetings of La Cosa Nostra leaders.

D’Amato and Sinatra were associated in the operation of the Cal Neva Lodge at Lake Tahoe, Nevada, during 1963. Salvatore “Sam” Giancana, long-time “boss” of the Chicago “family” of La Cosa Nostra, was frequently Sinatra’s guest at the Cal Neva Lodge during that period. These connections on the part of Sinatra provided a basis for the revocation of his gambling license in the State of Nevada and the disposal of his interest in the Cal Neva Lodge as well as the Sands Hotel in Las Vegas, Nevada.

Sinatra was present in 1947 in Havana, Cuba, with top leaders of La Cosa Nostra who had gone there to meet with Salvatore Lucania, more commonly known as Lucky Luciano, former “boss of bosses” of La Cosa Nostra in the United States. Luciano had entered Cuba surreptitiously from his native country, Italy, to which he had been deported under his parole from a New York State penitentiary where he had been serving a sentence on conviction for compulsory prostitution.

Sinatra has long been very friendly with the Fischettis, particularly Joseph and Rocco. The Fischettis were connected with the Chicago “family” of La Cosa Nostra once headed by their cousin, the late Al Capone. Their deceased brother, Charles Fischetti, was once “boss” of the Chicago La Cosa Nostra.

In addition to the foregoing,
that Joseph Colombo, a New York La Cosa Nostra leader, met with Sinatra
of Raymond Patriarca, New England La Cosa Nostra leader,
that Colombo was asked by Patriarca to meet with Sinatra because of a close friendship between the two. In prior years, Sinatra, together with his friend and fellow entertainer, Dean Martin, became a director of the Berkshire Downs Race Track in western Massachusetts.

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