John Roselli (Filippo Sacco) first became involved in crime when he worked for Al Capone in the 1920s. By the end of the Second World War Roselli had emerged as a senior crime boss in Las Vegas with close links to Meyer Lansky. In 1947 the Federal Bureau of Investigation (FBI) identified him as a leading figure in the Mafia and a close associate of Santos Trafficante.
In March I960, President Dwight Eisenhower of the United States approved a Central Intelligence Agency (CIA) plan to overthrow Fidel Castro. The plan involved a budget of $13 million to train "a paramilitary force outside Cuba for guerrilla action." The strategy was organised by Richard Bissell and Richard Helms.
Sidney Gottlieb of the CIA Technical Services Division was asked to come up with proposals that would undermine Castro's popularity with the Cuban people. Plans included a scheme to spray a television studio in which he was about to appear with an hallucinogenic drug and contaminating his shoes with thallium which they believed would cause the hair in his beard to fall out.
These schemes were rejected and instead Bissell decided to arrange the assassination of Fidel Castro. In September 1960, Richard Bissell and Allen W. Dulles, the director of the Central Intelligence Agency (CIA), initiated talks with two leading figures of the Mafia, Roselli (using the name John Rawlston) and Sam Giancana.
On 12th March, 1961, William Harvey arranged for CIA operative, Jim O'Connell, to meet Sam Giancana, Santo Trafficante, Johnny Roselli and Robert Maheu at the Fontainebleau Hotel. During the meeting O'Connell gave poison pills and $10,000 to Rosselli to be used against Fidel Castro. As Richard D. Mahoney points out in his book Sons and Brothers, The days of Jack and Bobby Kennedy (1999): "Late one evening, probably March 13, Rosselli passed the poison pills and the money to a small, reddish-haired Afro-Cuban by the name of Rafael "Macho" Gener in the Boom Boom Room, a location Giancana thought "stupid." Rosselli's purpose, however, was not just to assassinate Castro but to set up the Mafia's partner in crime, the United States government. Accordingly, he was laying a long, bright trail of evidence that unmistakably implicated the CIA in the Castro plot. This evidence, whose purpose was blackmail, would prove critical in the CIA's cover-up of the Kennedy assassination."
In 1961 Roselli persuaded Meyer Lansky, to join the conspiracy and was reportedly offering a million-dollar reward for the Cuban leader's murder. Richard Cain, a specialist in electronics and wire taps, was also recruited by Roselli. Cain took part in a failed attempt in March 1961 to poison Castro.
The nearest Rosselli came to killing Fidel Castro was in September 1961. Several Cubans were arrested at the intersection of Rancho Boyeros Avenue and Santa Catalina Avenue in Havana. The men were in two Jeeps armed with bazookas, grenade launchers, and machine guns. Two of those arrested, Guillermo Caula Ferrer and Higinio Menendez, made a full confession during their interrogation and admitted they had been working with CIA agents in Miami and had been trained on Guantanamo, the American naval base in Cuba. All the men involved in the plot were executed.
In April 1962, William Harvey took control of the ZR/RIFLE project. He told Johnny Roselli that Santos Trafficante and Sam Giancana had to cease involvement in the project to kill Castro. Ted Shackley, the new head of JM WAVE, also began to play a more important role in planning the assassination.
Eventually Rosselli and his friends became convinced that the Cuban revolution could not be reversed by simply removing its leader. However, they continued to play along with this CIA plot in order to prevent them being prosecuted for criminal offences committed in the United States.
In February, 1963, William Harvey was removed as head of the ZR/RIFLE project. Harvey was now sent to Italy where he became Chief of Station in Rome. Harvey was convinced that Robert Kennedy had been responsible for his demotion. A friend of Harvey's said that he "hated Bobby Kennedy's guts with a purple passion".
Harvey continued to keep in contact with Johnny Roselli. According to Richard D. Mahoney: "On April 8, Rosselli flew to New York to meet with Bill Harvey. A week later, the two men met again in Miami to discuss the plot in greater detail... On April 21 he (Harvey) flew from Washington to deliver four poison pills directly to Rosselli, who got them to Tony Varona and hence to Havana. That same evening, Harvey and Ted Shackley, the chief of the CIA's south Florida base, drove a U-Haul truck filled with the requested arms through the rain to a deserted parking lot in Miami. They got out and handed the keys to Rosselli."
In November, 1963, Roselli travelled to Arizona with a male friend and two women. He was being followed by the FBI but on the way to Los Vegas they lost contact with him. According to Tosh Plumlee, a pilot working for the CIA, he picked up Roselli from Tampa, Florida, early on the 21st November. Plumlee then took Roselli to New Orleans. After picking up several more men, Plumlee took Roselli and his friends to Garland where Roselli and some others got off. Plumlee then went to Redbird Airport in Dallas. In an interview in April, 1992, Plumlee claimed that he was told that the objective was "to abort the assassination" of John F. Kennedy.
Roselli discovered in 1966 that the FBI had been collecting information on his activities. Attempts were made to deport him as an illegal alien. Roselli moved to Los Angeles where he went into early retirement. It was at this time he told attorney, Edward Morgan: "The last of the sniper teams dispatched by Robert Kennedy in 1963 to assassinate Fidel Castro were captured in Havana. Under torture they broke and confessed to being sponsored by the CIA and the US government. At that point, Castro remarked that, 'If that was the way President Kennedy wanted it, Cuba could engage in the same tactics'. The result was that Castro infiltrated teams of snipers into the US to kill Kennedy".
Morgan took the story to Jack Anderson and Drew Pearson. The story was then passed on to Earl Warren. He did not want anything to do with it and so the information was then passed to the FBI. When they failed to investigate the story Anderson wrote an article entitled "President Johnson is sitting on a political H-bomb" about Roselli's story. It has been suggested that Roselli started this story at the request of his friends in the Central Intelligence Agency in order to divert attention from the investigation being carried out by Jim Garrison.
Roselli was eventually charged with being involved in illegal gambling in Las Vegas. In an attempt to obtain a lenient sentence, Roselli provided information in court about his role in helping the CIA with Operation Mongoose and ZR/RIFLE. The judge was not impressed and he was sent to McNeal Island prison. His good friend Fred Black intervened and used his powerful political connections to get transferred to a less harsh prison. Roselli was eventually released in 1973.
In 1975 Frank Church and his Select Committee on Intelligence Activities interviewed Roselli about his relationship with the secret services. It emerged from this interview that Roselli and fellow crime boss, Sam Giancana had taken part in talks with the CIA about the possibility of murdering Fidel Castro. Roselli also claimed that a CIA hit team that had been dispatched to Cuba had been "turned" and used to kill Kennedy.
The following year the Select Committee on Intelligence Activities decided to recall Roselli. Soon afterwards Fred Black called him and warned him that Santos Trafficante had taken out a contract on his life and that the "Cubans were after him".
In July 1976, Roselli left home in Florida to play golf. He never arrived at the golf course and ten days later 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.
Jack Anderson, of the Washington Post, interviewed Roselli just before he was murdered. On 7th September, 1976, the newspaper reported Roselli as saying : "When Oswald was picked up, the underworld conspirators feared he would crack and disclose information that might lead to them. This almost certainly would have brought a massive US crackdown on the Mafia. So Jack Ruby was ordered to eliminate Oswald."
The House Select Committee on Assassinations managed to obtain the records of an FBI wire tap on Santos Trafficante. On the tape Trafficante was heard to say "now only two people know who killed Kennedy and they aren't talking."