Read the CIA's 'Crown Jewels' files in full

The CIA worked with two of America’s top Mafia mobsters in a botched attempt to assassinate the Cuban President Fidel Castro with poisoned pills, according to previously classified documents released by the spy agency yesterday.

The extraordinary details of the 1960 plot were contained in more than 700 pages of documents that revealed some of the agency’s past illegal activities, including the targeting of foreign leaders, wiretapping of US journalists, CIA break-ins and thefts.

The documents are known as the CIA’s “Family Jewels” and relate to the period between the 1950s and early 1970s, an era of Cold War dirty tricks when successive administrations became obsessed with domestic radicals and the threat from Communism.

In one sheaf of documents that read like a cheap spy novel, the agency’s efforts to persuade Johnny Roselli, a mobster, to help plot the assassination of Castro are laid out in excruciating detail. A CIA memo, entitled The use of a member of the Mafia in an attempt to assassinate Fidel Castro, states that an agency official, Richard Bissell, approached Colonel Sheffield Ed-wards of the agency’s Office of Security in August 1960 to determine whether he “had assets that may assist in a sensitive mission requiring gangster-type action”. It adds: “The mission target was Fidel Castro.”

Roselli was believed by the CIA to be a high-ranking member of the crime syndicate, who controlled all the ice-making machines on the Las Vegas strip.

He was approached by a go-between, Robert Maheu, who believed that Roselli had connections leading into Cuban gambling interests. The story that Roselli was to be told was that several international businesses were suffering heavy financial losses in Cuba as a result of Castro’s action and that they were willing to pay $150,000 for his removal.

“It was to be made clear to Roselli that the US government was not, and should not, become aware of this operation,” a document states.

The pitch was made to Roselli at the Hilton Plaza Hotel in New York and Roselli was initially cool to the idea. But the contact led the agency to two top mobsters, Momo Salvatore “Sam” Giancana – Al Capone’s successor in Chicago – and Santos Trafficant, who were both on the US list of most-wanted men.

Giancana, who was known as Sam Gold, suggested that firearms might be a problem and that a potent pill that could be slipped into Castro’s food or drink might work. Six pills of “high lethal content” were provided to Juan Orta, identified as a Cuban official who had been receiving kickback payments from gambling interests and who still had access to Castro and was in a financial bind.

“After several weeks of reported attempts, Orta apparently got cold feet and asked out of the assignment. He suggested another candidate, who made several attempts without success,” the document said.

The plot was cancelled shortly after the Bay of Pigs debacle and the pills were retrieved by the agency. In 1976, Roselli’s body was found in a 55-gallon oil drum floating off the Florida coast.

The documents also show that the CIA wanted to assassinate Patrice Lumumba, Prime Minister of the Democratic Republic of Congo, General Rafael Trujillo, dictator of the Dominican Republic, and General René Schneider, the Chilean army commander. The CIA has always denied any responsibility for the subsequent murders of all three men.

Michael Hayden, the current CIA director, ordered that the documents be released “to provide a glimpse of a very different time and a very different agency.”

Times Recommends

• Should Knox’s trial even have reached the courtroom?
• 'Was it real?' The US bailout nightmare
• Iranian opposition plays the long game