Anti-Castro Cubans and the Mafia

Among conspiracy theorists, the most common suspects in JFK’s assassination are people associated with the Mafia, the CIA and/or anti-Castro Cubans. And there is some evidence, mostly unverifiable stories, to support each of these three groups. Indeed, we have some confessions:

Tony Cuesta

Herminio Diaz Garcia

Eladio del Valle

Anti-Castro Cubans

Fabian Escalante, a former head of Castro’s counterintelligence unit reported that Tony Cuesta, a Cuban exile prisoner confessed that he had been involved in JFK’s assassination along with Herminio Diaz Garcia and Eladio del Valle. Cuesta was a member of Alpha 66 and Commandos L. Herminio Diaz Garcia had been a gangster and hit man in Cuba under the Batista regime and in 1960 was a bodyguard for Santo Trafficante. Eladio del Valle also worked for Santo Trafficante and had been active in anti-Castro activities with Sergio Arcacha Smith, who was allegedly travelling to Dallas with Rose Cheramie.

Santo Trafficante

Sam Giancana

Carlos Marcello

Mafia

Santo Trafficante, mob boss of Florida was reported to have made comments about his role in the assassination. Jose Aleman testified to the HSCA that Trafficante told him in 1963 that JFK “is going to be hit.” After Chicago mob boss Sam Giancana was murdered, the House Select Committee on Assassinations was alleged to have obtained the records of an FBI wire tap on Trafficante. On the tape Trafficante was heard to say “now only two people are alive who know who killed Kennedy and they aren’t talking.”

The HSCA found "that it was possible, based on an analysis of motive, means and opportunity, that an individual organized crime leader, or a small combination of leaders, might have participated in a conspiracy to assassinate President Kennedy. The committee's extensive investigation let it to conclude that the most likely family bosses of organized crime to have participated in such a unilateral assassination plan were Carlos Marcello and Santos Trafficante.” In 1985 a confidential informant reported to the FBI that “CARLOS MARCELLO discussed his intense dislike of former President John Kennedy as he often did. Unlike other such tirades against Kennedy, however, on this occasion CARLOS MARCELLO said, referring to the President Kennedy, ‘yeah I had the little son of a bitch killed, and I would do it again. He was a thorn in my side. I wish I could have done it myself.’”

David Atlee Phillips

David Sanchez Morales

E. Howard Hunt

Rogue CIA Agents

Shortly before he died in 1986, David Atlee Phillips, Chief of Cuban Operations for the CIA in North America and based in Mexico City in 1963 reportedly told Kevin Walsh, former HSCA staff member, “My private opinion is that JFK was done in by a conspiracy, likely including American Intelligence officers.” Cuban exile Antonio Veciana had told the HSCA that he saw Phillips meeting with Lee Harvey Oswald prior to JFK's assassination.

Before his death David Phillips had been estranged from his brother James Phillips for many years. As described in an email exchange between researcher Gary Buell and David Phillips’ nephew, Shawn Phillips, Shawn’s father, James Phillips, became aware that his brother, David, had in some way been “seriously involved” in the JFK assassination. James and David argued about this vigorously and it resulted in an estrangement between them that lasted for almost six years. As David was dying of lung cancer, he called his brother. Even at this point there was apparently no reconciliation between the two men. James asked David pointedly, “Were you in Dallas that day?” David answered, “Yes,” and James hung up the phone on him.

David Sanchez Morales was Head of Operations at the CIA’s JM/WAVE station in Miami and heavily involved in training Castro assassination teams and later with death squads in South America. In HSCA investigator Gaeton Fonzi’s book, The Last Investigation, Fonzi recounts a story told by Morales’ close friends Bob Walton and Ruben Carbajal. After a night of heavy drinking in the spring of 1973, Morales flew into a rage and a long rant about JFK’s betrayal at the Bay of Pigs after which he stopped and said, “Well, we took care of that son of a bitch, didn’t we?” Morales also reportedly told friends, "I was in Dallas when we got the son of a bitch and I was in Los Angeles when we got the little bastard."

E. Howard Hunt was a CIA officer who worked with both Phillips and Morales on the successful 1954 coup against Jacobo Arbenz in Guatemala as well as the Bay of Pigs operation against Cuba. Prior to his death in 2007 he confessed involvement in JFK’s assassination, together with Phillips, Morales and several other CIA officers. Hunt fingered LBJ as the mastermind of the plot, together with with several CIA agents, Antonio Veciana: the anti-Castro Cuban leader of Alpha 66, and a Corsican gunman on the grassy knoll.

With all these alleged confessions who are we to believe? Well, maybe they're all correct. During the period 1959-1963, the CIA, Mafia and anti-Castro Cubans were all working together to assassinate Castro. In a variant of Johnny Roselli’s Political H-Bomb story to Jack Anderson, some conspiracy theorists think that the CIA/Mafia/anti-Castro Cuban assassination teams were turned on JFK, not by Castro, but by the teams themselves. In order to explore this theory, we need to look at the long history of Castro assassination plots, in order to understand the players. We’ll then return to more closely examine the proposed plotters.

History of Castro Assassination Attempts

1959

There are reports that prior to Castro’s takeover of Cuba on January 1, 1959 the Mafia and perhaps the CIA were involved in providing arms and money to Castro, most likely as a way to hedge their bets since the fall of the Bastista regime seemed inevitable. Although some in the CIA and Mafia were suspicious of Castro, in April of 1959 he travelled to the US, gave talks at Columbia, Harvard and Princeton and met with the CIA and Vice-President Nixon. However on May 17, 1959 Castro signed the first Agrarian Reform Law limiting privately owned sugar cane land to 3,300 acres per owner. Castro had closed the Havana casinos when he took over, but then reopened them under government control, until they were finally shut down in 1961. Meyer Lansky headed the Mafia casino effort under Batista, but Santo Trafficante and other mob figures owned casino interests. So by the spring of 1959, both the US Government and the Mafia casino interests had turned against Castro. Frank Fiorini Sturgis claimed that in early 1959 he was offered $1 million by Meyer Lansky to assassinate Castro but the American Embassy in Havana would not authorize the hit. In March 1959 there was allegedly a second assassination attempt by four of Rolando Masferrer’s men, together with (according to Cuban accounts) David Morales of the Havana CIA station.

According to Lamar Waldron, Ultimate Sacrifice p 324, Jimmy Hoffa, the leader of the Teamsters Union, served as go between between the CIA and the mob on a third Castro assassination attempt in June 1959, this time involving Pennsylvania mob boss Russell Bufalino and Cleveland gangster Dominick Bartone. Hoffa was working on a deal to sell planes and jeeps to Castro in order to get close enough to Castro to assassinate him. There is evidence that Bartone’s partner, a man who went by the name of Jack La Rue, was actually Jack Ruby, with partial corroboration by Jack Ruby’s sister and Robert McKeown. The plan fell through when Bartone was arrested by US Customs agents. Bobby Kennedy was investigating Hoffa in the Senate Labor Rackets Committee and uncovered the Bartone plane deal but was unable to determine the identity of Bartone’s partner “Jack La Rue”.

The 1959 plots against Castro were led by the old Havana casino Mafia crowd, with the CIA playing a background role. This changed in 1960 when planning started for what was to become the Bay of Pigs. In December 1959 J.C. King, Chief of CIA’s Western Hemisphere Division advocated that “thorough consideration be given to the elimination of Fidel Castro.” In the summer of 1960 Richard Bissell, who was the CIA officer in charge of the future Bay of Pigs invasion, contacted Sheffield Edwards, head of the CIA’s Office of Security and asked him to find someone who could assassinate Castro. Edwards contacted former FBI agent Robert Maheu who brought in mobster Johnny Roselli, who in turn brought in Sam Giancana and Santo Trafficante. The CIA needed the mob because the old Havana casino crowd had friends in Havana who could help with the operational aspects. The mob welcomed the involvement with the CIA because it helped to shield them from prosecution from the FBI and Justice Department. Vice President Nixon who was overseeing the Bay of Pigs operations on behalf of the administration desperately wanted the CIA to “get off their tails and do something.” The toppling of Castro would be “a real trump card” for the 1960 election. During 1960 the invasion plan morphed from a small guerrilla infiltration to a large paramilitary invasion force, and the operation wasn’t ready to go until well after the 1960 November election. An assassination of Castro was apparently part of the Bay of Pigs plan, using poison pills provided by the CIA to a Havana colleague of Tony Varona, a Cuban exile leader. However, the assassination plot was so tightly held that E. Howard Hunt, not knowing of the plot, locked up Varona together with other Cuban exile leaders so they couldn’t get a jump on establishing a new Cuban government. With Varona incommunicado, he was unable to get word to his colleague and the poison pill plot failed.

The CIA's Assassination Program: ZR/RIFLE

During 1960 the CIA decided to professionalize their assassination program and assigned William Harvey, head of the CIA’s Staff D department to develop an assassination capability with the cryptonym ZR/RIFLE. Staff D was responsible for code breaking. It was an ideal place within the CIA to house an assassinations capability because it was unusually secretive and often worked with local lock pickers, safe crackers and gangsters. By this time, the CIA had learned not to put references to assassination in writing. Approvals were all done orally, for the purposes of plausible deniability. When the Church Committee investigated CIA assassination of foreign leaders, they found very few documents, and the participant’s memories became very hazy. Fortunately, handwritten notes on ZR/RIFLE surfaced from Bill Harvey’s personal effects after his death, despite two burglaries and ransackings of his house. They can be seen HERE.

These notes include the following assassination guidelines: “Never mention word ‘assassination’… no projects on paper… strictly person to person, singleton ops, planning should include provision for blaming Sovs or Czechs in case of blow… should have phony 201 (file) in RG (Central Registry) to backstop this, all documents therein forged and backdated… should look like a CE (counter espionage/counter intelligence) file… [executive action would] require most professional, proven operationally competent, ruthless, stable, CE-experienced ops officers.”

Castro Assassination Attempts 1961-1962

Following the failed Bay of Pigs invasion in 1961, there were several Castro assassination attempts using poison pills as well as a rifle/mortar/bazooka attack organized by Antonio Veciana with the CIA’s David Atlee Phillips. In November 1961, Bill Harvey was asked to target his ZR/RIFLE capability against Castro and started working with Johnny Roselli, who was given the nominal rank of Colonel. The administration’s efforts to oust Castro were organized under a task force named the Special Group (with Bobby Kennedy, called Special Group Augmented) under the leadership of counterinsurgency expert General Edwin Lansdale. The plan to oust Castro was called Operation Mongoose and consisted of a series of raids and propaganda efforts against Cuba. In April 1962 there was also a large amphibious invasion military exercise including 40,000 Marine and Navy personnel, Operation Ortsac (Castro spelled backwards) with military plans for an invasion in the fall of 1962. The CIA’s work for Special Group Augmented, mostly through the Miami JM/WAVE station was organized under Task Force W. In November 1961, Harvey recruited the CIA’s David Morales, who had been forced to flee Havana, to become Director of Operations at JM/WAVE. During 1962 Harvey and Morales worked very closely together with “Colonel” Roselli based in CIA training camps in the Florida Keys working with Cuban exile sniper teams. There were several assassination attempts on Castro thought to be linked to Roselli’s team, including a sniper attack in Oriente Province in November 1962 on a motorcade which killed a driver and Castro’s lookalike bodyguard, Captain Gamonal, a March 13, 1963 attempt using rifles, machine guns, and grenades, and an April 7, 1963 grenade and pistol attack.

It is unknown how many attempts were made to assassinate Castro. In 1975 Castro gave George McGovern a Black Book with information on 24 assassination attempts that Castro knew of which he claimed involved the CIA. It is an open question as to whether JFK or Bobby Kennedy knew of these assassination attempts. The Church Committee investigated this and learned that Bobby Kennedy was told of the contact between the CIA and Giancana and Trafficante and responded “I hope this is followed up vigorously.” Given the culture of deniability, ZR/RIFLE and assassination plans were not discussed at the level of Special Group Augmented. JFK made public statements deploring the use of assassination by the US, and Bobby Kennedy made statements against working with underworld figures. However, some assassination researchers believe that Bobby’s zeal to oust Castro would have led him to sanction the use of assassination, and that his depression following JFK’s death might have been due to guilt from a sense of complicity over his involvement in Castro assassination attempts which backfired.

Cuban Policy Changes in 1963

The Cuban Missile Crisis ended with a pledge by JFK not to invade Cuba. During 1963, the US continued to plan for regime change in Cuba, but they tried to move anti-Castro assassination and invasion teams off shore in Nicaragua, under a program called AMWORLD. Following the Cuban Missile Crisis, on October 30, 1962 RFK terminated “all sabotage operations” against Cuba. During the crisis, Bill Harvey had sent several teams into Cuba without the authorization of the SGA. Bobby Kennedy, who shared a mutual loathing with Harvey was furious and terminated him from Cuban operations; Harvey was transferred to be CIA Station Chief in Rome in June of 1963. Larry Hancock posits that the infiltrations during the Cuban Missile Crisis may have been assassination teams that Harvey could not disclose. During 1963 Cuba planning changed course from exile raids to a plan for a “palace coup”, where a moderate within Castro’s administration would overthrow Castro and his brother and declare a new course for the Cuban revolution free of Soviet involvement. At the same time, starting in June 1963, the administration opened a dual track of rapprochement with Castro, offering to end the embargo and normalize relations if he would cut his ties to the Soviets and forswear fomenting revolution in South America. Details can be found in the files of Joseph Califano.

Despite the official termination of the Castro assassination program, Harvey, who had become very close with Roselli, continued to meet with Roselli during the spring of 1963, expensing a boat trip with him to the ZR/RIFLE accounts and calling him to Washington for an all night meeting in June, just before Harvey left for Rome. David Morales, head of operations at JM/WAVE in Miami also continued to work closely with Roselli.

Bradley Ayers, an Army officer assigned to assist in the paramilitary training of CIA backed Cuban exiles wrote a book titled The War that Never Was: An Insider’s Account of CIA Covert Operations Against Cuba, in which he describes seeing elite snipers training in Colonel Roselli’s training camp in the Florida Keys in the summer of 1963. Ayers may not be trustworthy, but if he is, this effort in 1963 would be in direct opposition to Bobby Kennedy's orders.

Evidence of Cuban Exile Involvement in JFK's Assassination

There are certainly a number of stories about anti-Castro Cubans who may have been involved with Oswald or JFK's assassination:

In Week 2: Dealey Plaza, we saw several reports of people who saw a dark complected man, either Black, or Mexican or perhaps Cuban on the sixth floor of the TSBD and driving away in a Nash Rambler. Some conspiracy theorists believe the dark complected man could be either the CIA's David Morales or Herminio Diaz Garcia.

In Week 6: Secret Service, we heard stories of Lee Harvey Oswald associating with anti-Castro Cubans who may have been posing as pro-Castro supporters during the summer of 1963. These stories were told by Richard Case Nagell, in Dick Russell's book, The Man Who Knew Too Much, as well as by Sylvia Odio and Robert McKeown.

Another story about Oswald and anti-Castro Cubans is the story by Harold Reynolds of Abilene Texas. He claimed to have seen a note to his Cuban exile neighbor Pedro Valeriano Gonzalez on Sunday November 17, 1963, signed by Lee Oswald with two Dallas phone numbers.

In Week 6: Secret Service, we saw the reports of two JFK assassination attempts, one in Chicago which purportedly included anti-Castro Cubans, and one in Tampa which included a potential patsy, Gilberto Policarpo Lopez.

The Parrot Jungle story which was verified by co-workers involved a recent Cuban exile talking about his friend Oswald who lived in Texas, had been to Russia and was an excellent shot. This friend, named Lee, hated Kennedy and "could shoot him between the eyes".

John Martino was an electronics expert who worked in the Havana casinos before Castro took over. He allegedly told his wife on the morning of 11/22, "Flo, they're going to kill him (Kennedy). They're going to kill him when he gets to Texas."

Larry Hancock’s research turned up two of Martino’s associates: Felipe Santiago Vidal and Roy Hargraves, who may have played roles in the assassination. Vidal had known of JFK’s peace feelers with Castro in the fall of 1963 and they both spent time in Dallas in October. Roy Hargraves was reported to be a heavily armed ex-Marine who had Secret Service credentials in his possession and a neighbor of his said of Roy that “Somebody is going to die.” and “It will be the biggest thing this country has ever seen.” Some people think that the picture below, depicting two men on Elm Street just after the assassination are Felipe Vidal Santiago and Roy Hargraves:

Photomontage supplied by James Richards

Finally we have two stories that Cuban exiles who were trained to assassinate Castro turned and killed JFK instead. The first story was the Political H Bomb story told by columnist Jack Anderson in 1967 and sourced from Johnny Roselli’s lawyer. The second one was told by Gene Wheaton to the ARRB. Wheaton said that he was told by CIA officer Carl Elmer Jenkins and Cuban exile Raphael (Chi Chi) Quintero that Jenkins had trained assassination teams and that both Jenkins and Quintero were involved in JFK’s assassination.

So what are we to make of all these stories? Many could be lies or disinformation, so the heaviest weight should be the evidence which emerged prior to the assassination. Many of the stories concern people associated with the Havana casino crowd. Many of the Cuban exiles were connected to Alpha 66. Larry Hancock has done a great deal of research tracking the involvement of various suspects and pulled together a plausible scenario of their involvement in the assassination in a book published online at MaryFerrell.org, called Tipping Point.

Evidence of Mafia Involvement in JFK's Assassination

J. Edgar Hoover's FBI did not look into the possibility of Mafia involvement in JFK's assassination for two reasons: Hoover avoided exploring any evidence of conspiracy because the implications of Russian conspiracy could lead to nuclear war, and for a long time Hoover specifically denied the existence of a national level Mafia. Hoover's favorable treatment towards the Mafia could have been because they had compromising material on him or because they did him favors, or both. According to Anthony Summers in his book Official and Confidential: The Secret Life of J. Edgar Hoover, Hoover and his partner, Clyde Tolson used to vacation each year and gamble at the Del Mar Race Track in California where the Mafia would let him keep his gambling winnings and cover his losses. One summer Billy Byars Jr, son of the Humble Oil millionaire, asked Hoover "Do you think Lee Harvey Oswald did it?" "And he stopped and he looked at me for quite a long time. Then he said, 'If I told you what I really know, it would be very dangerous to this country. Our whole political system could be disrupted."

Besides the pseudo-confessions of Santo Trafficante and Carlos Marcello noted above, what additional evidence is there for Mafia participation in JFK’s assassination? The Mafia certainly had motive, as Bobby Kennedy’s Justice Department crusade against the Mafia and Jimmy Hoffa had impacted their operations. Marcello loathed the Kennedys, especially after RFK deported Marcello to a remote airstrip in Guatemala and he almost died on the long trek back to civilization. However, motive alone is not sufficient to support a charge of involvement in JFK’s assassination.

Robert Blakey, the chief counsel of the HSCA, published a book titled The Plot to Kill the President: Organized Crime Assassinated JFK. Blakey started with the HSCA conclusions: that Oswald fired three shots that killed JFK and wounded Governor Connolly and an unidentified gunman fired a shot from the Grassy Knoll that missed. Blakey’s conclusion that organized crime assassinated JFK goes beyond the HSCA which concluded that the Mafia may have been involved. However Blakey offers only two pieces of circumstantial evidence to support an Oswald association with the mob. Oswald’s uncle, Dutz Murret was a bookie in New Orleans in Carlos Marcello’s organization. And Oswald’s friend David Ferrie did work for Carlos Marcello, although he also certainly worked with anti-Castro Cubans and was reported to be a contract agent with the CIA. If associations with the mob are proof of conspiracy, we should not leave out Dallas County Sheriff Bill Decker, whose recommendation led to early parole for Dallas mobster Joe Civello, and who was lifelong friends with Dallas mobster R.D. Matthews.

Besides the alleged statements by Trafficante and Marcello, the most significant evidence linking the mob to JFK’s assassination is Jack Ruby’s murder of Lee Harvey Oswald. Ruby’s action appeared to many as a classic mob style execution, presumably to keep Oswald from talking. The Warren Commission dismissed any association of Ruby with the mob by having the FBI interview Ruby’s lifelong Chicago friend and mob executioner, David Yaras and asking Yaras if Ruby was affiliated with the mob. Yaras wisely said no. However, the HSCA looked more deeply and found that Ruby had many connections, not only with the Mafia in his hometown of Chicago, but more importantly with members of the Las Vegas/Havana gambling syndicate.

Jack Ruby's Relationship with the Dallas Police

Born Jacob Rubenstein in 1911, Jack Ruby grew up in a Chicago slum with seven siblings, a disturbed mother and an alcoholic and abusive father. At the age of 16 “Sparky” as he was known quit school and took to the streets in search of a quick buck or a fight. He ran errands for Al Capone’s betting operation, sold peanuts, chocolates, race track tip sheets, discount jewelry, newspaper subscriptions, hot music sheets, and punchboard chances. He was an off key singing waiter and a bouncer, a sharp dresser with a hot temper who would often get into fistfights, whenever anyone made disparaging remarks about Jews. In 1933, both Ruby and Johnny Roselli moved from Chicago to Los Angeles; Roselli ran the gambling operations at Santa Anita racetrack and Ruby sold handicapper’s tip sheets at the track. By 1939 Ruby was back in Chicago working as a “union organizer” for the Scrap Iron and Junk Dealers Union, which by that time was mob controlled and described by the AFL-CIO as largely a shake down operation. After the founder of the union was murdered by its President, Paul Dorfman, the union was renamed the Chicago Waste Material Handlers Union and taken over by Dorfman, who later was central to the mob takeover of the Teamster’s Central States Pension Fund under Jimmy Hoffa. Ruby served in the Army Air force from 1943 to 1946 as a Private First Class.

In 1947, Paul Rowland Jones was arrested for attempting to bribe the new Dallas County Sheriff Steve Guthrie in order for the Chicago mob to take over gambling, prostitution and illegal drug rackets in Dallas. Jones was also arrested for smuggling 57 kilograms of opium from Mexico. (see McClennan Committee page 12526). Douglas Valentine, in The Strength of the Wolf, noted that both Jack Ruby and his brother Hyman (who had been convicted of possessing 2 ounces of heroin in 1937) were suspects in Jones' drug deal. In 1964 Jones told the FBI that he met Ruby in 1947 and learned that Ruby was connected to the Chicago syndicate. Ruby moved to Dallas in 1947; Dallas businessman Giles Miller claimed that Ruby told him he “had been exiled from Chicago and although he had wanted to go to California he had been directed to go to Dallas.” Ruby ran a number of nightclubs, together with his sister Eva Grant. In 1950 Ruby briefed the Kefauver Committee about organized crime in Chicago, with an agreement that the Kefauver Committee not ask him any questions about Dallas. Louis Kutner said that his staff learned that Ruby was a syndicate lieutenant who had been sent to Dallas to serve as a liaison for Chicago mobsters. Both the Warren Commission and the HSCA depicted Ruby as a small time unsuccessful nightclub operator and downplayed his role as liaison with Dallas law enforcement. Bobby Gene Moore was a part time employee from 1952 to 1956 of both Joe Civello, mob boss of Dallas and Jack Ruby and told the FBI that Ruby was a frequent visitor and associate of Civello’s who he suspected of being involved in narcotic smuggling and illegal gambling. Moore also described payoffs to judges and police; in the McClellan Hearings, Dallas Lieutenant George Butler said the Chicago mob “had some plans to have decisions handed down by certain judges that they controlled, which practically handcuffed the law-enforcement field in their fight against narcotics.” After Civello was convicted of a narcotics charge in the 1930’s, he obtained early parole at the recommendation of Dallas County Sheriff Bill Decker. In 1956, Bunny Breen, wife of convicted narcotics trafficker James Breen told the FBI that “James got the OK to operate through Jack Ruby of Dallas.” Jack Hardee told the FBI that “in order to operate in Dallas it was necessary to have the clearance of Jack Ruby who had the ‘fix” with the county authorities.” Mike Ryan, the former bookkeeper of Ruby’s Carousel Club is alleged to have said that “Ruby is the payoff man for the Dallas Department and whenever liquor and gambling raids were to be made on the Dallas underworld, Ruby would always be contacted first.”

By all accounts Ruby enjoyed a very close relationship with the Dallas police, perhaps more so than would be warranted by a strip club owner who gave out free passes and discounted drinks to cops. It was estimated that he was on a first name basis with hundreds of the over 1,000 Dallas police. Officer Tippit’s attorney Travis Kirk said that Homicide Captain Will “Fritz and Jack Ruby were very close friends. Jack Ruby, in spite of his reputation of being a ‘hood’, was allowed complete run of the homicide bureau.” The Chicago FBI surfaced a report that Ruby had made trips with the Dallas Police Chief to a gambling resort in Hot Springs, Arkansas.

Part of Ruby’s influence with the Dallas Police may have been as an informant, a tactic which mobsters like Joe Civello used to curry favor with the police. Richard Clark, Dallas Police Detective working narcotics and vice used to call Ruby once per month. Sergeant Patrick Dean, who was in charge of the Dallas Police Headquarters security when Oswald was shot, and who failed a lie detector test regarding basement security, admitted that he knew Ruby and was reportedly on good terms with mobster Joe Civello. It’s possible that Ruby’s good relationship with many in the DPD was due to his role in directing payoffs to the police, a position that both the Warren Commission and the HSCA would seek to downplay. But whether from free passes to strip clubs, government informant status or payoffs, Ruby’s relationship with the Dallas police was remarkable; according to Seth Kantor, his rap sheet showed that he was arrested nine times in sixteen years for infractions including attempted murder and pistol whipping an off duty cop, but was convicted only once and charged $35 for having ignored a traffic summons.

Ruby and Cuba

As Castro’s revolution was gearing up in 1958, Ruby may have tried to get in on the action by applying for a license to import firearms. As we saw above, Lamar Waldron reviewed a great deal of evidence showing that Ruby was involved in a deal to sell planes and jeeps to Cuba in 1959 with his friend at the Havana Tropicana hotel, Lewis McWillie and mobster Dominic Bartone, which may have involved a Castro assassination plot. Ruby also travelled to Havana in 1959 with his friend McWillie and visited Santo Trafficante who was at that time imprisoned by Castro. Ruby may have been attempting to help get Trafficante freed from a Cuban jail. Robert McKeown who was close to Castro told the FBI that Ruby had visited him and offered him $25,000 for a letter of introduction to Castro in order to help free some friends of his who had been imprisoned by Castro. Ruby told McKeown that he was also interested in selling Castro jeeps and slot machines. Ruby’s sister, Eva Grant, recalled the attempted jeep sales. According to Lamar Waldron, when Ruby’s partner Bartone got arrested, the deal fell through. Ruby also admitted sending McWillie four Colt Cobra pistols at McWillie’s request; a Cuban gangster was subsequently arrested with a Colt Cobra in a Castro assassination plot.

Ruby Comes Into Money

During 1963 Ruby was under financial pressure from the IRS to which he owed $39,129. In June Ruby’s tax attorney contacted the IRS and told them that Ruby was ready to settle. He had apparently decided to borrow the money from the Chicago Mafia. Ruby placed calls in June to a delegation of Chicago mobsters who were in Dallas to discuss taking over the prostitution business there. But Kantor theorizes that the mob’s terms were too stiff and his debt wasn’t settled. Starting in October 1963, Ruby’s out of state phone calls soared. There is a report from a former FBI man based on FBI surveillance records that Ruby met with Johnny Roselli in October 1963 in Miami. On November 11, 1963, an old Chicago friend of Ruby’s, Alexander Gruber showed up to visit after not seeing Ruby for over a decade. In 1963 Gruber was a Teamsters' organizer and associate of Meyer Lansky. The next day Paul Rowland Jones showed up to visit with both men. The following week Ruby called Lenny Patrick, an old friend of Ruby’s who was a hit man in Chicago. On November 16, Ruby was seen by two people in Las Vegas at the Tropicana Hotel where his friend Lewis McWillie worked. On November 19 Ruby told his lawyer that he had a connection who would supply him with the funds to settle his IRS debt. Ruby signed a power of attorney to allow his attorney to negotiate on his behalf and purchased a safe for his office. On the afternoon of November 22, Ruby’s banker Bill Cox at the Merchants State Bank met with Ruby and estimated that Ruby had $7,000 in cash with him. There were several reports that Ruby received the money in Chicago in late October from Hoffa associate Allen Dorfman.

Ruby's Killing of Oswald

It is clear to those who have studied Ruby that he was not a mastermind of the JFK assassination. He may not have known that the President was going to be assassinated. Some speculate that Ruby's job was to organize the DPD manhunt for Oswald, perhaps being told that Oswald was a commie who was just going to stage a protest. Even though on the morning of the assassination Ruby asked an associate if he would "like to watch the fireworks" at JFK's motorcade, about ten minutes after the assassination Ruby was seen by advertising salesperson Richard Saunders at the Dallas Morning News and Ruby appeared uncharacteristically silent and pale. Ruby was next seen inquiring about JFK's condition at Parkland Hospital by reporter Seth Kantor. Kantor said Ruby "looked miserable. Grim. Pale. There were tears brimming in his eyes." At 2:37pm Ruby called Alex Gruber in Los Angeles. Ruby closed his club for the weekend and visited his sister Eva Grant. She told the Warren Commission that he was tremendously upset; he went into the bathroom and threw up. Later that evening Ruby was seen at Dallas Police headquarters posing as a reporter; at a news conference he was filmed correcting Henry Wade, telling him that Oswald had been involved in the Fair Play for Cuba Committee. Late that evening Ruby spent time with Dallas Police Officer Harry Olsen and his girlfriend Kathy Kay Coleman who was a stripper at Ruby's club. Olsen had allegedly spent the afternoon guarding a house a few blocks away from where Officer Tippit had been killed.

For the next 36 hours, a timeline shows that Ruby was hanging around the Dallas Police station, seemingly stalking Oswald. Between 2 and 3am Sunday morning four calls went out to the Dallas Police, the Dallas Sheriff’s office and the FBI warning that if they moved Oswald the way they were planning he would be killed. The Dallas Police officer who took the call recognized Jack Ruby’s voice. On Sunday morning many people saw Ruby around the Dallas Police station. Reserve Sergeant Kenneth Croy who was first on the scene of the Tippit murder and Police Sergeant Patrick Dean are thought by some to have let Ruby into the locked basement of City Hall. At 11:21am, as Oswald was being led past a crowd of reporters to be transferred to the county jail, Ruby jumped out and shot Oswald once, killing him. Ruby was hustled upstairs while Oswald was transported to Parkland Hospital. Police Officer Don Archer described Ruby after the shooting as nervous, sweating and hyperactive. However, Ruby calmed down completely when he received the news of Oswald's death. Detective Archer noted his profuse sweating stopped at once. 'I would say his life had depended on him getting Oswald.'"

Ruby's Trial and Death

Ruby’s first visitor in jail, and frequent visitor thereafter was allegedly Joe Campisi, Joe Civello’s number two man in the Dallas Mafia. Ruby’s brother Earl took over Jack’s business and arranged to hire San Francisco lawyer Melvin Belli. But Belli’s partner Seymour Ellison said that the job came from a former Havana casino contact in Las Vegas who said, “Sy, one of our guys just bumped off that son of a bitch that gunned down the President.” Ruby had told Secret Service Agent Forrest Sorrels that he shot Oswald to spare Jackie Kennedy the burden of coming to Dallas to testify and also to show that a Jew had guts. He also told the police that he had wanted to help the city of Dallas "redeem" itself in the eyes of the public, and his grief over the assassination had finally "reached the point of insanity," suddenly compelling him to shoot when Oswald walked in front of him in the basement that Sunday morning. And he said he had intended to shoot Oswald three times. Melvin Belli tried to defend Ruby using an insanity plea based on "psychomotor epilepsy." That was not successful; on March 14, 1964, Ruby was convicted of murder with malice and was sentenced to death. Ruby got a new lawyer for an appeal who brought in consulting psychiatrist Dr. Jolyon West. West had done research for the CIA's MKUltra mind control program using hypnosis, LSD and truth serum for, among other things, Elaboration of techniques for implanting false information into particular subjects, or for confusing them, or for inducing in them specific mental disorders. On April 22, 1964, the first day that West examined Ruby, Ruby suffered a psychotic break with auditory and visual hallucinations, and delusions that all the Jews in America were being slaughtered. Under Dr. West's care, Ruby's mental health deteriorated so that he seemed crazy and anything he said could be discounted. When Chief Justice Earl Warren took Jack Ruby's testimony on June 7, 1964, Ruby begged to be taken to Washington DC to give testimony because he claimed his life was in danger in Dallas. Ruby said "I want to tell the truth, and I can't tell it here." But Earl Warren told Ruby there was no way they could get him to Washington D.C. Ruby's conviction was overturned in October 1966 when the appeals court ruled that the trial should have had a change of venue. But Ruby shortly afterwards was diagnosed with cancer and died in January 1967. Ruby was convinced that Dr. Jolyon West had injected him with cancer cells.

Did Ruby kill Oswald because he was crazy and distraught over JFK's death, or did his friends in the mob pressure him to silence Oswald?

Other Untimely Deaths

David Ferrie: In February, 1967 Jim Garrison, District Attorney of New Orleans was investigating David Ferrie, Guy Banister, Carlos Bringuier, Eladio del Valle and Clay Shaw for conspiracy to murder JFK. When it was reported in the newspapers that Ferrie was a suspect, Ferrie called a Garrison investigator and said, "You know what this news story does to me, don't you. I'm a dead man. From here on, believe me, I'm a dead man." Five days later, Ferrie was found dead in his appartment with two typed suicide notes. An autopsy discovered that he had died of natural causes: a brain aneurysm, or perhaps an ice pick through the ear.

Eladio del Valle: Twelve hours after Ferrie was found dead, Eladio del Valle, was found dead in a parking garage in Miami. He had been tortured, shot in the heart at point-blank range, and his skull split open with an axe. Diego Gonzales Tendera, a close friend, later claimed de Valle was murdered because of his involvement in the assassination of President John F. Kennedy.

Dorothy Kilgallen: Kilgallen was a nationally syndicated reporter who had developed an interest in and was working on a book on the JFK assassination. She interviewed Jack Ruby and told a friend "In five more days I'm going to bust this case wide open." On the evening of November 7, 1964 she went out to meet a "mystery man" contact. The next day she was found dead of a barbituate and alcohol overdose. She was found sitting upright in a bedroom she didn't use, clothed in bedclothes she didn't normally wear, wearing false eyelashes, with a book she had already read on her lap and no eyeglasses nearby. None of her notes and writings on the assassinations were found. She had given a chapter of her book to a friend for safekeeping, but the friend, Florence Pritchett died two days later of a cerebral hemorrhage and the chapter was never found.

Sam Giancana: On June 19, 1975, shortly before he was scheduled to testify to the Church Committee about CIA and Mafia collusion, Sam Giancana, mob boss of Chicago, was found shot to death in his basement kitchen.

Johnny Roselli: Roselli did testify to the Church Committee and told them how he had recruited Sam Giancana into the CIA assassination plots about Castro. He also told them that a CIA hit team that had been dispatched to Cuba had been turned by Castro and used to kill JFK. The following year the HSCA called Roselli to testify. A good friend of Roselli called him and told him that Santo Trafficante had taken out a contract on his life. Roselli didn't live to testify to the HSCA. In July 1976 his body was found floating in an oil drum in Miami's Dumfoundling Bay. He had been garroted. Roselli's legs had been sawed off and squashed into the drum with the rest of his body.

David Sanchez Morales: David Morales, who had been Chief of Operations at the Miami CIA station and had trained anti-Castro assassination teams, kept a very low profile and was never identified or called to testify by any of the JFK investigative committees. Morales left the CIA around 1973 and built a house in Elfrida, Arizona, close to the Mexican border. Morales told a friend, Robert Walton, that he had put in the best security system in the United States. Walton said, “What do you need so much security for? You're still thirty miles from the Mexican border.” Morales replied, “I'm not worried about those people, I'm worried about my own." In May 1978 Morales was called to Washington, D.C. Ruben Carbajal had a drink with Morales a few days later. Carbajal told him he looked unwell. He replied: “I don’t know what’s wrong with me. Ever since I left Washington I haven’t been feeling very comfortable”. That night he was taken to hospital. Carbajal went to visit him the next morning. As Carbajal later recalled: “They wouldn’t let no one in, they had his room surrounded by sheriff’s deputies.” Later that day (8th May) the decision was taken to withdraw his life support. Morales’s wife, Joanne, requested that there should not be an autopsy. He was 53 years old.

We'll close this chapter with a story that proves that fiction can be as strange as real life. One curious incident that Johnny Roselli didn’t tell the Church Committee about was his involvement in 1948 as a financier of a Hollywood B movie titled He Walked by Night. The plot involved a murderous ex-serviceman who, like Oswald, kept his rifle wrapped in a blanket. In one scene he’s stopped by a cop on a deserted street. When the cop asks him for ID the ex-serviceman shoots the cop and runs away. Do you think that plot line was somehow reused in the plot on November 22, 1963?

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