CIA–Mafia plots to assassinate Fidel Castro

The CIA–Mafia plots against Fidel Castro emerge in the book as a covert alliance whose secrecy was threatened when the press and the Senate began drawing attention to it. The alleged operation connects Russell Bufalino and Sam Giancana to the U.S. Central Intelligence Agency, and its exposure becomes part of the dangerous background to Giancana’s killing.

Reports and the alleged operation

A week before Giancana was killed, Time reported that Russell Bufalino and Giancana had worked for the U.S. Central Intelligence Agency in 1961 during the Bay of Pigs invasion of Cuba and in a 1962 plot to kill Castro. The account places two different episodes under the same shadow: the failed invasion and a subsequent assassination scheme. For Bufalino, the disclosure had a personal danger as well as a political one; the narrator says that seeing his name in print was what drove him especially mad.

The Senate had subpoenaed Giancana to testify about the CIA hiring the Mafia to assassinate Castro. Four days before he was due to appear, he was shot in his kitchen: once in the back of the head and six times under the chin, which the narrator describes as a Sicilian signal that he had been careless with his mouth. The scene suggested an assailant close enough to share the room and its ordinary domestic work. In the book’s account, Giancana’s death thus follows the public reporting of the alleged covert relationship and prevents his scheduled testimony from bringing it further into view.

The poison-pill allegation

The book places the reported collaboration earlier than the 1962 assassination scheme. In its account of the Senate Church Committee’s findings, Russell Bufalino was implicated in a plot with the CIA to kill Fidel Castro using poison pills shortly before the April 1961 Bay of Pigs invasion. The committee’s conclusion turns the episode from a generalized claim of mob assistance into a specific alleged method and a sharply defined moment: the pills were intended to be used just before the invasion. The account does not describe how the plan was to be carried out or whether the pills were ever deployed; it presents the committee’s finding as evidence of a covert conspiracy, not as a completed assassination attempt.

Cuban stakes and the wider network

The assassination allegations sat within a longer struggle over the mob’s Cuban interests. Before Fidel Castro toppled Fulgencio Batista in 1959, Russell Bufalino had owned a racetrack and a major casino near Havana; the revolution cost him both properties and a great deal of money. The book also describes Teamsters pension money flowing into ventures that included casino construction in Havana and Las Vegas, placing the alleged CIA–Mafia operation amid business interests already tied to Cuba. In June 1975, as the Senate Church Committee examined the CIA’s connections to organized crime, Time reported Bufalino’s alleged help in a conspiracy to use poison pills against Castro shortly before the Bay of Pigs invasion. The report joined a secret political operation to the mob’s lost Cuban assets and existing financial reach, while placing Bufalino’s name in public circulation at a moment of heightened scrutiny.

Testimony and evidentiary frame

The account reaches the reader through the book’s interview-based history of Frank Sheeran, not through a scene in which the covert operation is independently reconstructed. Charles Brandt first interviewed Sheeran in 1991, but Sheeran ended that session after having disclosed more than he wanted to; after a later meeting, he agreed to renewed questioning, and the interviews continued for four years. Brandt brought prosecutorial and interrogation experience to those conversations, while taking care that Sheeran’s statements would not become legally admissible confessions. Sheeran read and approved each chapter and then the full manuscript. That process establishes how the book’s account was assembled and endorsed by its subject, while leaving the operation itself presented as an allegation rather than a completed killing of Castro.