The hit man and the mobster: Jack Ruby and Santos Trafficante

130 Comments / Assassination, Question / By Arnaldo M. Fernandez

Why did Jack Ruby kill Lee Oswald?

Gail Raven,” an exotic dancer, was friends with Jack Ruby, the Dallas nightclub owner who killed Lee Harvey Oswald.

When Ruby’s friend Gail Raven was asked that question, the former exotic dancer told JFK Facts: “He had no choice. Jack had bosses, just like everyone else.” Raven said she did not know who those bosses were.

Joe Shimon, a well-connected Washington cop, told syndicated columnist Jack Anderson that Ruby had received specific orders from a famous former Havana crime boss. “Santos Trafficante called in the mob’s chits with Ruby and ordered him to kill Oswald,” Anderson wrote in his 2000 memoir, Peace War and Politics.” (p. 117.)

Both the Warren Commission (1964) and the House Select Committee on Assassinations (1978) investigated the two men and found no significant link between them. But in the 1990s, two officials from the Cuban government’s security service concluded that Trafficante played key roles in a conspiracy to kill President Kennedy.

So who’s right? Is it possible that Trafficante was one of the bosses of Ruby to whom Gail Raven alluded? Was Jack Anderson correct when he wrote that Ruby killed Oswald at the behest of Trafficante?

Trafficante’s Career

Santos Trafficante Jr. was the son of Santos Trafficante Sr., who owned several casinos in Havana. When his father died in 1954 he took control of these establishments. He was known as an organized crimes figure. He attended a notorious convention of Mafia bosses held in the upstate New York town of Apalachin on November 14, 1957. When the meeting was raided by the police, Trafficante was arrested. He said his last name was “Santos” and managed to get himself released; he made his way back to Cuba.

On January 23, 1958, the Cuban police arrested Trafficante for questioning about “The Apalachin Meeting.” After Fidel Castro took power in Cuba in January 1959, Trafficante was arrested again. This time it wasn’t for questioning. Castro had ordered a raid against all the foreign citizens involved in the gambling business, and Trafficante was arrested on June 10, 1959. The detainees were declared subject to deportation and sent to the immigration detention center at Tiscornia near Havana.

Santos Trafficante
Santos Trafficante (center) escorted by Cuban police officers on January 1958.

Ruby told the Warren Commission he had only visited Havana once on vacation, but Cuban immigration records told a different story. Ruby had entered Cuba from New Orleans on August 8, 1959, and left on September 11, 1959. He re-entered from Miami on September 12, 1959, and returned to New Orleans on September 13, 1959.

That was not the only evidence that Ruby had been in Havana.

After Ruby killed Oswald, a British journalist, John Wilson Hudson, called the U.S. Embassy in London to report that he had been incarcerated at Tiscornia during the summer of 1959. He said that “an American gangster called Santo [had been] visited by an American gangster type named Ruby.”

According to British journalist Anthony Summers, Robert McKeown, a gunrunner in Texas, said that Ruby hoped to meet Castro to arrange the release of some unnamed friends detained in Havana.

But while Ruby seems to have visited Havana while Trafficante was detained there, there is no corroboration of Hudson’s claim that they met.

It is known that Trafficante got permission to attend his daughter’s wedding on August 18, 1959, and was allowed to leave Tiscornia. He testified to HSCA that he appeared in person at his deportation hearings in October and November 1959. Although he was spotted back in the United States around January 1960, there is no record of him leaving Cuba under his alien number 93461.

Ruby was known to have been in Dallas on August 10, 21, 31, and September 4, 1959, according to FBI and Dallas police. Thus, it seems that Ruby was able to get in and out of Cuba without going through immigration and customs. By the same token, Trafficante could have left Cuba by yacht or private plane.

There is no doubt that Trafficante was involved in various joint ventures of the CIA and Mafia to kill Castro between September 1960 and April 1962. Another crime boss, Sam Giancana, approached him and Trafficante agreed to recruit an asset for carrying out the assassination. Trafficante and Giancana were dropped from the project in 1962 on the the orders of Richard Helms, deputy director of the CIA. Helms gave “explicit orders” to Bill Harvey, the chief of Cuba operations and the agency’s assassination program, not to collaborate with the two gangsters.

And there is evidence that Trafficante was aware of efforts to assassinate JFK.

José Alemán, a friend of Rolando Cubela, told journalist George Crile III that he met with Trafficante at the Scott Bryan Hotel in Miami in June 1963. When he mentioned in passing “that Kennedy would get reelected, Trafficante reportedly replied, ‘No, José, he is going to be hit.’”

When the HSCA asked Aleman to explain Trafficante’s comment, he chickened out, suggesting implausibly that Trafficante meant JFK would be “hit with a number of votes.”

Cuba’s account

Fabian Escalante, retired chief of counterintelligence for Cuba’s Dirigencia General de Inteligencia gave more details to a group JFK researchers in Nassau, Bahamas, in 1995.

Fabian Escalante
Fabian Escalante, retired Cuban intelligence officer.

Trafficante had received permission to attend his daughter’s wedding from Rolando Cubela, a former commandante who had a position in the Castro government, according to Escalante. It seems that Trafficante’s lawyer, Rafael García-Bango, was a friend of Cubela’s.

In 1963, the CIA would attempt to enlist Cubela, known by the code names AMLASH, in a scheme to kill Castro. In 1966 Cubela and Garcia-Bango would be arrested, convicted, and sentenced to jail terms for their roles in the plot.

[More on the case of Rolando Cubela here.]

Escalante also told the Cuban version of events to Claudia Furiati, a Brazilian journalist and author of the book entitled “ZR-RIFLE,” the code name of the CIA assassination program. “Like Ruby, Trafficante was a small-time Mafia capo,” she wrote (see p. 114). In fact, neither Ruby nor Trafficante fit that description.

Nonetheless, Escalante concluded from data in the Cuban government’s still-undisclosed JFK files that both were the third-level players in the plot to kill the American President. According to Escalante, the chief mastermind at the top level may have been deputy director Helms, with senior operations officers David Atlee Phillips and Howard Hunt acting as transmission belts in the second level.

The fourth-level players — the shooters — were organized in two teams, according to Escalante. The American mobsters Richard Cain, Lenny Patrick, and Dave Yara were coordinated by Ruby. Escalante contended that Trafficante coordinated the Cuban exiles Herminio Diaz and Eladio del Valle, former Trafficante bodyguard and drug courier, respectively.

In 2013, Richard Cain’s brother Michael told JFK Facts that he had investigated Richard’s alleged role in JFK’s assassination and concluded he was not in Dallas on November 22.

Ruby gets ready

Jack Ruby, upper right, expert on the Fair Play for Cuba Committee.

“The murder of Oswald by Jack Ruby had all the earmarks of an organized crime hit, an action to silence the assassin, so he could not reveal the conspiracy,” wrote HSCA General Counsel G. Robert Blakey and co-author Richard Billings in their book, “The Plot to Kill the President.” (See p. 339.)

After Oswald was arrested, 90 minutes after JFK was killed, Ruby began stalking him.

When Oswald was brought out to speak with reporters later that night, District Attorney Henry Wade said the suspected assassin was a member of “the Free Cuba Committee.” From the last row, a “newsman” wearing glasses corrected Wade:

“Fair Play for Cuba,” he called out.

The  fact-checker was Ruby, a nightclub operator, who was not a reporter and not known to wear glasses. Oswald was led back to his cell.

Thirty-six hours later, Ruby strolled into the basement of the Dallas Police Department headquarters with a loaded pistol in his pocket, just as Oswald was being led out to be transferred to another jail. A phalanx of cops guarded the suspect, but left his front unprotected. Ruby walked up and shot and killed Oswald.

On March 20, 1964, Warren Commission assistant counsels Leon Hubert and Burt Griffin sent a memo to General Counsel J. Lee. Rankin, stating, “The most promising links between Jack Ruby and the assassination of President Kennedy are established through underworld figures and anti-Castro Cubans, and extreme right-wing Americans.”

Neither the Warren Commission nor the HSCA seems to have pursued these leads far enough.

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Published by Nelle

I am interested in writing short stories for my pleasure and my family's but although I have published four family books I will not go down that path again but still want what I write out there so I will see how this goes

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