Cuba

Cuba is an offstage center of loss and political intrigue in the book. Although much of the island’s significance is recalled from elsewhere, its casinos and racetracks help explain the anger of powerful mob figures, the alliances surrounding Jimmy Hoffa, and the reported convergence of organized crime and the U.S. Central Intelligence Agency in anti-Castro operations. Frank Sheeran’s recollections make the island both a place of vanished wealth and a distant cause of events unfolding in the United States.

Casinos, Exile, and Lost Property

The account places the mob’s rupture with Cuba in the period when Fidel Castro was expelling its members and confiscating their casinos, racetracks, houses, and bank accounts. Sheeran recalls traveling there with Russell Bufalino as the confiscations were beginning. He describes Bufalino as exceptionally angry, and says that a later trip was worse because Santo Trafficante had been arrested by the Communists and held in jail. Sheeran had heard that Sam Giancana sent Jack Ruby to distribute money in an effort to secure Trafficante’s release and get him out of Cuba; the book presents this as a rumor he heard, not as something he witnessed.

The financial losses were concrete. With the approval of Cuban dictator Fulgencio Batista, Bufalino had owned a racetrack and a major casino near Havana. Castro’s seizure of those properties cost him both. The episode helps explain why Cuba appears in the narrative not simply as a foreign setting but as lost territory whose value continued to shape the interests and grievances of men based in the United States. Bufalino also had secret interests in Las Vegas casinos, but Cuba’s confiscated holdings were among the assets the book specifically connects to his earlier position on the island.

Anger on the Road

One memory compresses that grievance into an oddly intimate detail. In 1960, Bufalino and Meyer Lansky were on a boat leaving Cuba when Castro’s takeover and the loss of the casinos weighed heavily on Bufalino. Sheeran says that Bufalino smoked cigarette after cigarette and quietly cursed Castro. Jimmy Blue Eyes saw an opportunity to bet him twenty-five thousand dollars that he could not go a year without smoking. Bufalino threw his cigarette overboard and, according to Sheeran, never smoked again—even after the year had passed and the bet had been paid.

The anecdote gives the island’s political consequences a personal measure: anger at dispossession becomes the setting for a wager, and the wager becomes a lasting break with tobacco. Sheeran also recalls being told that the losses in Cuba amounted to a million dollars a day. The figure belongs to the recollected account, but its function is clear: it conveys the scale of the losses as the men around him understood them. Bufalino’s close friends included Carlos Marcello and Trafficante, and the book depicts all three as especially hostile to Castro’s seizure of their interests. Trafficante’s imprisonment made that hostility personal as well as financial.

From Lost Assets to Covert Operations

Cuba also drew figures who did not share the same political judgment. In a conversation recalled elsewhere in the book, Giancana argued that John F. Kennedy would help the mob remove Castro and recover its casinos. Hoffa distrusted the Kennedy brothers after the McClellan hearings and expected President Nixon to win and assist them in Cuba; Giancana countered that the original events had unfolded under Dwight Eisenhower and Nixon. Their discussion, as Sheeran presents it, joined the fortunes of the island to domestic politics and to the men’s calculations about which administration might serve their interests.

Sheeran describes being drawn into one operation through a truck assignment. He drove a load of war matériel from Maryland to a dog track in Florida, where it was handed over to E. Howard Hunt and anti-Castro Cubans. Afterward, Sheeran went to Kingston to report to Bufalino. Bufalino told him that something was going to happen in Cuba and that Hoffa had called on him because Hoffa was keeping an open mind about the Kennedy administration. In Sheeran’s account, Hoffa cooperated out of respect for Giancana and Bufalino and because recovering Cuba could benefit everyone involved, even if it also benefited the Kennedys.

The invasion that followed did not restore the lost property. Sheeran recalls learning on television that President Kennedy had withheld American air cover for the Bay of Pigs invasion. He describes the anti-Castro force as exposed on the beach, with no ships offshore to shell the land above the beachhead; some invaders were killed and others captured. His account turns the failed invasion into another reversal in the Cuba story: a plan associated with recovering the island’s assets ended in defeat rather than return.

The Plot and the Limits of Recollection

Sheeran says that he later flew with Bufalino to the Gold Coast to meet Trafficante and others. He emphasizes that he did not hear anyone, including Bufalino, discuss a plan with the Kennedy administration to kill Castro with poison or a bullet. He says that reports of such a plot appeared in newspapers years later. This distinction matters: his account places him near people and operations connected to Cuba, while also marking the limit of what he personally says he heard.

The book sets that recollection beside the 1975 Senate investigation chaired by Frank Church. The Church Committee examined suspected mob ties to the Bay of Pigs invasion and a CIA–mob plot to assassinate Castro. According to the book, the U.S. Central Intelligence Agency admitted to the committee that the mob had been involved in and assisted with the invasion, as well as acknowledging the existence of a plot to kill Castro. The reported assassination scheme, primarily involving poison, was called Operation Mongoose; the committee concluded that Bufalino was part of a conspiracy involving poison pills intended for use before the April 1961 invasion.

This contrast leaves Cuba at the intersection of testimony, recollection, and later investigation. Sheeran’s reported proximity does not mean he claims to have witnessed every operation, while the committee account supplies a public record of a covert relationship he says he did not hear discussed. Across these different kinds of evidence, Cuba’s narrative significance rests on the same chain of consequences: Castro’s seizure of property drove anger and recovery schemes, and those schemes entangled mob figures, Hoffa, and American political and intelligence activity.