U.S. Central Intelligence Agency

The U.S. Central Intelligence Agency appears in the book not as a fully documented institutional portrait but as a powerful outside actor whose anti-Castro operations intersected with the criminal networks surrounding Russell Bufalino and Sam Giancana. The account links intelligence activity to mob leaders who had lost casinos and other property in Cuba, then returns to that connection when Senate scrutiny and a killing make the cost of exposure visible. The book’s claims are consequential, but its presentation also makes clear that the agency’s covert relationship with these figures is reconstructed through reporting, committee findings, and Frank Sheeran’s recollections rather than laid out as a complete operational record.

Anti-Castro operations and Bufalino

The central allegation concerns the period around the Bay of Pigs invasion. In its account of Senate Church Committee hearings, the book says that the U.S. Central Intelligence Agency recruited Russell Bufalino’s help in a plot to assassinate Fidel Castro. The Church Committee concluded that Bufalino was part of a conspiracy involving poison pills intended for Castro shortly before the April 1961 invasion. This places Bufalino, described elsewhere as a far-reaching Mafia power broker, inside an operation that joined intelligence aims to underworld access.

The account also connects Bufalino and Giancana to more than one phase of anti-Castro activity. Time magazine reported in June 1975 that the two had worked on behalf of the U.S. Central Intelligence Agency in 1961 in connection with the Bay of Pigs invasion and in a 1962 plot to kill Castro. The book presents this report as especially sensitive for Bufalino: seeing his name in print was, Sheeran recalled, the sort of exposure that enraged him. The difference between a covert connection and a public report is therefore central to the episode; the relationship that depended on secrecy became news just as federal investigators were examining the agency’s ties to organized crime.

Cuba, lost assets, and criminal networks

The political context was also personal and financial. The book describes mob leaders whose Cuban casinos were taken from them after Castro came to power. Russell Bufalino, Carlos Marcello, and Santo Trafficante are identified as close associates angered by the loss of their Cuban interests; Trafficante had also been jailed in Cuba. Sheeran recalls that Bufalino repeatedly cursed Castro during a boat trip after the casinos had been lost. The account thus sets the anti-Castro plots against a material grievance: Cuba was not an abstract policy question for these figures but a place where they had possessed businesses and money.

The reported intelligence connection sits within a broader network of meetings, messages, and personal ties. Sheeran says he drove with Bufalino to gatherings at Joe Sonken’s Gold Coast Lounge in Hollywood, Florida, where figures from around the country met. Bufalino met there with Trafficante and Marcello, and Sheeran encountered Trafficante’s lawyer, Frank Ragano, who was later loaned to Jimmy Hoffa to assist with trials. This does not establish that every person in the network participated in U.S. Central Intelligence Agency operations. Rather, it shows how the book situates the reported plots within a cross-regional world where criminal leaders, intermediaries, union relationships, and political concerns could overlap.

The wider labor context sharpens that distinction. The Teamsters pension fund, created under Hoffa, became a source of loans to organized crime, while Bufalino was among the figures with whom Hoffa did business. The book presents this as a separate channel of influence, not as proof that pension lending was part of an intelligence operation. Its juxtaposition with the Cuba material instead shows the breadth of the relationships through which powerful figures could move: shared commercial interests and private meetings on one side, a reported covert anti-Castro collaboration on the other.

Senate scrutiny and the danger of exposure

In 1975, the connection became a matter of public and congressional attention. The book places the reporting about Bufalino and Giancana during the Senate Church Committee hearings on the U.S. Central Intelligence Agency’s ties to organized crime. Giancana had been subpoenaed to testify about the agency’s hiring of mob figures to assassinate Castro. According to Sheeran’s account, Giancana was killed in his kitchen four days before he was due to appear, shot from behind and then beneath the chin. The timing makes the suppressed testimony part of the narrative’s pressure, but the passage does not establish who ordered the killing or demonstrate that the U.S. Central Intelligence Agency caused it.

Sheeran’s recollection of Bufalino’s maxim, “When in doubt have no doubt,” gives the episode a terse language of certainty that sits uneasily beside the gaps in the record. The Senate inquiry, the press report, and the killing converge in the narrative, but convergence is not the same as proof of a single chain of command. The book uses the episode to convey the stakes of speaking about covert alliances while keeping the identity of Giancana’s killers unresolved in the cited account.

The agency within the book’s larger account

The U.S. Central Intelligence Agency’s place in the narrative is defined by this narrow but consequential intersection with organized crime. The book attributes to the agency a recruitment effort involving Bufalino and reports a wider relationship with Giancana; it does not provide a complete account of the agency’s structure, decision-making, or internal procedures. Its emphasis falls instead on the intermediaries and circumstances through which covert action became entangled with criminal power, and on the risk that a secret relationship could become public through a magazine report or Senate subpoena.

That entanglement also borders the book’s account of Hoffa’s disappearance without establishing an intelligence role in it. The narrative notes that Hoffa kept a yellow pad beside his phone with the words “Russ & Frank,” referring to Bufalino and Sheeran, and that investigators later focused on a group of suspects that included both men. These details belong to the separate Hoffa investigation; they do not show that the U.S. Central Intelligence Agency participated in Hoffa’s disappearance. Their proximity to the Cuba material instead underlines the book’s recurring picture of overlapping personal and criminal networks, whose connections could be politically significant while remaining difficult to disentangle or conclusively prove.