Nixon, Sinatra and the Mafia

Sep 12, 2009 - by Don Fulsom - 0 Comments

Updated Feb. 23, 2010

Frank Sinatra

Frank Sinatra

Both Nixon and Sinatra had deep ties to the Mafia. It was only natural that after President John Kennedy dumped Sinatra that Ole Blue Eyes hooked up with the biggest politician in the Mob’s pocket. Sinatra hung around with Nixon and Vice President Agnew so much he even acquired a Secret Service code name, “Napoleon.”

by Don Fulsom

John Kennedy banished Frank Sinatra from Camelot when the singer’s Mafia ties clashed with the President’s crackdown on organized crime. But those well-documented ties didn’t keep President Richard Nixon—a big recipient of Mob payoffs—from wooing the popular crooner away from the Democratic Party.

The courtship actually started with Nixon’s unsavory vice president, Spiro Agnew—who first got together with Sinatra during the Thanksgiving holiday in 1970. They enjoyed each other’s company so much that Agnew became a regular houseguest at Frank’s (Palm Springs) place, and made 18 visits in the months that followed. 

 The two men played golf together, dined out, talked through the night in Frank’s den, and on one occasion watched the porn movie Deep Throat together.  Frank’s guest quarters, once remodeled for John F. Kennedy, were eventually renamed “Agnew House,” according to Anthony Summers and Robbyn Swan in Sinatra:  The Life.

Nixon and Sinatra

The President himself evinced a keen interest in Sinatra’s possible endorsement during a Sept. 13, 1971 Oval Office meeting with top aide Bob Haldeman. Nixon was in the middle of a rant against the IRS for investigating some of his friends (including preacher Billy Graham, movie actor John Wayne, Bebe Rebozo and Robert Abplanalp), when he worried aloud over whether he could obtain Sinatra’s support.  

Nixon ordered Haldeman to look into Sinatra’s possible ties to Democratic presidential hopeful Sen. Edmund Muskie:  “(The IRS is) after, you know, every one of our people.  Goddamnit, they were after me … Somebody told me that Muskie used Frank Sinatra’s plane in California.  Did you hear that?  Maybe we should investigate that.”

Haldeman was hot on the case the next day. In a Sept. 14th memo, he sought a secret White House probe to discover “whether this is true.  If so, check with the Vice President’s office and find out how this jibes with the reports that Sinatra wants to support the President … As you probably know, we’ve received reports from a number of directions that Sinatra was on our side.  His supplying a plane to Muskie would not seem to be evidence of that.”

The Haldeman memo, sent to key assistants and stamped “Administratively Confidential,” was declassified in 2010.

In another newly released confidential memo dated Sept. 16, 1971, Haldeman staffer Gordon Strachan cites the probe’s main findings:  Muskie had indeed used a plane jointly owned by Sinatra and Danny Schwartz, a San Francisco Democrat and supporter of Hubert Humphrey.  Schwartz okayed Muskie’s use of the plane.  But most important, Strachan reported, "The Vice President’s Office (Roy Goodearle) reports that 'Sinatra is still with us.’”

Strachan’s investigation also determined that aide Chuck Colson was pressing “very hard to have Sinatra introduced to the President quietly,” but that Attorney General John Mitchell opposed the idea—though, possibly, Mitchell’s mind could be changed.

The Strachan memo ends brightly for those favoring a solid Nixon-Sinatra alliance:  “The net result is that Sinatra is still with us and could be brought into full endorsement if he met the President, if this were deemed appropriate.”

On Oct. 25, 1971, Chuck Colson—Nixon’s top political advisor—sent out a “Confidential/Eyes Only” memo to Haldeman.

Also released in 2010, the Colson memo recommends an informal “one-on-one” White House meeting, over drinks, between the President and the Mob-tainted singer. Colson suggests that if such a session were held—and a number of other steps were taken—“we are relatively certain to have completed our seduction of Frank Sinatra.”

In the memo, Colson concluded that a personal relationship between the President and Sinatra could yield major campaign contributions because “(Sinatra) has a great deal of control over what we understand to be massive financial resources.”

The Colson memo does not contain a single cautionary word about Sinatra’s longtime ties to the Mafia.  But the proposed one-on-one meeting apparently never took place.

When a House committee sought to question Sinatra about his Mob ties in 1972, Agnew unsuccessfully tried to delay the service of a subpoena.  When Sinatra did testify, he was surly and defiant. President Nixon personally phoned Sinatra to congratulate him for stonewalling the panel.

At least Nixon had the good political sense to reject Agnew’s attempt to get a top government post for Sinatra—director of the American Revolution Bicentennial Administration. Nixon aide John Ehrlichman said he “gulped” when Agnew phoned him with that suggestion.  Agnew, in his “high singsongy voice,” pitched the crooner for the job because Sinatra was what Agnew called a “world-renowned figure, an ethnic, an Italian and an able executive,” Ehrlichman remembered in Witness to Power.

Ehrlichman promised the vice president he’d pass the suggestion on to Nixon.  “But,” he added, “I’d seen Sinatra’s thick FBI package, full of innuendos about connections with organized crime.  I couldn’t imagine trying to get him through a Senate confirmation.”  Sinatra’s FBI file ran to 1,275 pages, 36 pages more than Carlo Gambino’s. When Ehrlichman did tell Nixon about Agnew’s off-the-wall idea (Nixon had long before concluded that Agnew was lazy, incompetent and dumb), he said the President “just laughed.”  The bicentennial job eventually went to future U.S. Republican Sen. John Warner of Virginia.

Nixon, Roselli and Sinatra

Sinatra ultimately headed “Entertainers for Nixon,” which did not require Senate confirmation or a background check into the singer’s “thick FBI package,” which included tight links to major Mafia figures like Johnny Roselli.  Indeed, “Ole Blue Eyes” even sponsored Roselli for membership in the exclusive Friar’s Club of Beverley Hills. Roselli was tossed out, however, after he was indicted for fixing key gambling operations there.

Roselli also had several Nixon connections. In the early 1960s, he was a key Mob contact in the CIA’s plot to kill Cuban leader Fidel Castro. Vice President Nixon initiated that plot. The CIA gave Roselli the rank of a colonel.

Roselli once claimed to a fellow gangster that he, Roselli, was one of the shooters who murdered President Kennedy in Dallas on November 22, 1963. Roselli’s gangland associate, striptease club owner Jack Ruby, of course, went on to kill the alleged lone assassin of Kennedy, Lee Harvey Oswald.  

Roselli and Ruby may have known each other since 1933.  Roselli said Ruby was “one of our boys” and that Ruby shot Lee Harvey Oswald to silence him.

In All American Mafioso, Charles Rappleye and Ed Becker say Roselli and Ruby met at two small hotels in Miami during October 1963.

In 1975, shortly after agreeing to testify before Congress about the JFK murder, Roselli’s decapitated and dismembered body was found floating in an oil drum off the coast of Florida. Major Nixon benefactor Santos Trafficante was suspected of the murder.

Chicago godfather Sam Giancana (a confederate of Roselli, Ruby and Trafficante) had actually been talking to Senate investigators about the JFK assassination, but was rubbed out while under police protection in his own suburban Chicago home. He died on June 19, 1975—shot in the back of the head, and then six times around his mouth.  The method of the murder matched Mob symbolism for “talks too much.”

Santos Trafficante—who survived the internal Mafia warfare—was tight with Nixon’s closest buddy, Bebe Rebozo. Trafficante—who had controlled many Mob operations in Cuba before Fidel Castro’s revolution—directed secret Nixon-instigated Mob/CIA plots to snuff Castro.  In the mid-1970s, the House Assassinations Committee concluded that Trafficante “had the motive, means, and opportunity” to plan and carry out the murder of President Kennedy. 

 In 1992, former Mob lawyer Frank Ragano disclosed that he had once carried a message to Trafficante and New Orleans godfather Carlos Marcello that Teamsters chief Jimmy Hoffa wanted them to kill President Kennedy.  In 1959, while in one of Castro’s jails, Trafficante was visited by Jack Ruby—who reportedly helped arrange for Trafficante’s release.

Sinatra, JFK and Nixon

Frank Sinatra, the greatest popular singer of the 20th century, was a high-strung alcoholic whose ties to organized crime were "woven into the fabric of his life and career," according to author Anthony Summers. Frank usually carried a pistol in a shoulder holster.

Sinatra is credited with deliberately pairing Mob mistress Judith Campbell Exner (whose other lovers included Sinatra, Roselli and Chicago godfather Sam Giancana) with presidential candidate John Kennedy.  Sinatra also introduced JFK to Hollywood Sex Goddess Marilyn Monroe. 

 After President Kennedy was forced to dump Judith Exner—and stop associating with Sinatra—Frank hooked up with the biggest politician in the Mafia’s pocket, Richard Nixon.   He hung around with Nixon and Agnew so much he even acquired a Secret Service code name, “Napoleon.”

Sam Giancana, the dapper don of Chicago, was so tight with Sinatra he always wore a star sapphire pinky ring, a gift from the Mafia’s favorite entertainer.  And Sinatra had such great affection for Giancana, he would end every personal performance with a tribute to Sam, “My Kind of Town, Chicago is.”

By 1960, Giancana had had been arrested some 70 times and had reportedly ordered some 200 torture-murders of men who had done him wrong.  Sinatra’s friend, movie actor Peter Lawford (President Kennedy’s brother-in-law), told Sinatra biographer Kitty Kelley that “when the word got out around (Hollywood) that Frank was a pal of Sam Giancana, nobody but nobody ever messed with Frank Sinatra.  They were too scared.  Concrete boots were no joke with (Giancana).  He was a killer.”  Kelley conducted the interview with Lawford for her book, His Way.

Giancana, Sinatra and Nixon

Sam Giancana later blamed Sinatra for failing to persuade his buddy, the newly elected President Kennedy, to turn a blind eye toward the Mafia in exchange for the election victory Giancana had helped swing Kennedy’s way in 1960.  At one point, the Chicago godfather was so incensed, he considered having Sinatra bumped off.  But Sinatra never got more than a chilling warning.

Early in the JFK years, the singer received a traditional Mafia death threat, according to Sinatra the Life by Anthony Summers and Robbyn Swan.  When a silver dome was lifted off a silver room service dinner tray in Sinatra’s Miami Beach hotel suite, the skinned head of a lamb was displayed as the main course.

Summers and Swan also note: "According to a member of (Giancana’s) family, only the intercession of East Coast associates persuaded Giancana not to have Frank killed in 1963. 'That motherf****r, ' he said when Frank arrived unexpectedly at the Armory Lounge (in Chicago), 'is lucky to be alive'."

Unlike Sinatra, Richard Nixon was always on the best of terms with Giancana. 

The Chicago godfather’s half-bother Chuck and nephew Sam claimed in their 1992 book Double Cross that Nixon and Giancana had a mutually rewarding relationship that dated back to the 1940s.

In recounting for his relatives major government help Nixon gave him back then, Giancana also established a direct link between Nixon and a Chicago gangster who later moved to Texas and went on to shoot the alleged assassin of President Kennedy, Lee Harvey Oswald: "Nixon's done me some favors, all right, got us some highway contracts, worked with the unions and overseas,” Sam asserted. “And we've helped him and his CIA buddies out, too. Shit, he even helped my guy in Texas, (Jack) Ruby, get out of testifying in front of Congress back in forty-seven … By sayin' Ruby worked for him." 

 A 1947 FBI memo confirms this—asking that Ruby be excused from testifying before Congress because “he is performing information functions for the staff of Congressman Richard Nixon, Republican of California.”

Mob Ties of Sinatra, Nixon

Frank Sinatra's Mob ties go back to at least 1947, when he was photographed with the notorious Lucky Luciano on a balcony of the Hotel Nacional in Havana.  Luciano, who headed the world’s largest illegal drug cartel, was in Havana for a convention of about one dozen American crime bosses, including Trafficante, Marcello, and the owner of the Nacional, Meyer Lansky.  Sinatra used the occasion to give Luciano a gold cigarette case that was inscribed, "To my dear pal Lucky, from his friend, Frank Sinatra."

Nixon’s Mafia connections went way back too. In his first race for Congress, in 1946, Nixon won the secret financial support of Mickey Cohen—the head of the Syndicate in California—with the approval of East Coast Mob financial genius Meyer Lansky.  Lansky had developed pre-Castro Cuba for Mafia gambling, prostitution, drug trafficking, and other nefarious activities.

In the early 1950s, Meyer Lansky met Richard Nixon and Bebe Rebozo in Havana, where Nixon lost a reported $50,000 at one of Lansky’s gambling casinos—but Rebozo picked up his buddy’s marker. Lansky operated in Havana with the approval of—and with millions of dollars in cash payoffs to—Cuban dictator Batista.  Nixon embraced and lauded Batista during an official vice presidential visit to Cuba.

Most of Nixon's Havana gambling occurred at Lansky's Hotel Nacional, where Nixon got the royal treatment—including complimentary stays in the Presidential Suite.

 As far back as 1951, Bebe Rebozo—Nixon’s almost constant companion—had been involved with Lansky in illegal gambling rackets in southern Florida. Former crime investigator Jack Clarke said Rebozo was pointed out to him, back then, as ''one of Lansky's people …When I checked the name with the Miami police, they said he was an entrepreneur and a gambler and that he was very close to Meyer.''

When Fidel Castro took over Cuba and shuttered Havana’s casinos, Lansky put out a $1-million contract on Castro.  This went hand-in-hand with Vice President Nixon’s secret CIA/Mafia plans to eliminate the Communist leader of the island nation only 90 miles from U.S. shores.

Nixon, Agnew and Sinatra

 President  Nixon finally lured Sinatra out of retirement so that he could sing at a White House State Dinner for Italian Prime Minister Giulio Andreotti in April 1973.  In introducing Sinatra, the President lavishly praised the singer—even comparing him to the Washington Monument, “the Top.”  Andreotti—who had alleged Mafia links in Italy—expressed his gratitude to Nixon for inviting Sinatra: “I am going to be able to listen to him singing here. This is something which will give much prestige to me with my children.”

Nixon did not keep up his contacts with Sinatra—at least not publicly—after the 37th chief executive was forced to resign over the Watergate scandal in the summer of 1974.

But Sinatra proved to be Agnew’s true friend and financial savior after Nixon’s vice president quit the job in 1973 over bribery and tax evasion charges.  Sinatra made several big loans to Agnew—including one of $200,000—so the disgraced politician could pay fines and back taxes…as well as help out with, in Agnew’s words, “family expenses until I could find some way to make a living.”

In Go Quietly…or Else, Agnew wrote, “As time went by and my business improved through my numerous trips abroad, I earned an adequate income and paid back the last of the Sinatra loans in 1978.”

After his resignation, Agnew faded into political obscurity and totally cut himself off from Nixon—refusing to even take any phone calls from the fallen president. Agnew did, however, maintain his strong loyalty to Sinatra. Visitors to Agnew’s mansion in Rancho Mirage, California, were greeted by a bust of Sinatra on top of the former vice president’s piano.

 In 1995, a bust of Agnew was finally installed with those of other vice presidents in the U.S. Capitol. 

 --Sources in addition to those cited include: Peter Lawford by James Spada; Encyclopedia of the JFK Assassination, by Facts of File;; Very Strange Bedfellows by Jules Witcover; The Arrogance of Power by Anthony Summers; Abuse of Power by Stanley Kutler; and the Nixon Presidential Library @

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