Fidel Castro

Fidel Castro’s decisive significance in this account is the upheaval his rule brought to organized crime’s Cuban empire: after toppling Fulgencio Batista, his government removed mob figures from the island and took their casinos and other property. The resulting losses were financial and political, and the resentment they provoked surfaces in Frank Sheeran’s recollections of mob leaders and in later reporting about a plot against Castro. He does not appear in a scene with Sheeran; instead, he is presented through the interests, anger, and secondhand accounts of men whose power his revolution disrupted.

Revolution and the Loss of Cuban Assets

Castro toppled Batista in 1959. Under Batista, Russell Bufalino had owned a racetrack and a major casino near Havana, with Batista’s blessing. Castro’s government took those properties when it expelled mob figures from Cuba. Bufalino also had secret interests in Las Vegas casinos, but the Cuban seizures represented a direct loss of assets and a rupture in the criminal network’s access to the island.

The book conveys the scale of that loss through Sheeran’s account of mob leaders’ anger. He recalls that figures associated with casinos in Cuba lost a million dollars a day after Castro took power and removed them from the island. That figure is presented as part of the men’s own grievance, not as an independently established accounting. In this telling, Castro’s revolution was not merely a change of government: it closed off a lucrative arena in which organized crime had invested and expected to keep operating.

A Grievance Told Through Bufalino

Sheeran recalls traveling with Bufalino and hearing about the latter’s anger toward Castro. On a boat leaving Cuba in 1960, Bufalino smoked repeatedly and cursed Castro softly. Sheeran also says Castro had put Santo Trafficante in jail. The account describes the mob’s response through its own intermediaries: Sam Giancana allegedly sent Jack Ruby to Cuba to distribute trading stamps in an effort to secure Trafficante’s release and departure from the country. That episode is reported as something Sheeran had heard, rather than as an event he witnessed.

The recollection also turns Bufalino’s anger into an anecdote about self-control. Jimmy Blue Eyes wagered $25,000 that Bufalino could not stop smoking for a year. Bufalino threw his cigarette overboard, quit at once, and did not resume smoking after the year had passed and the wager had been paid. The story gives the resentment a concrete setting and a small, telling reversal: the man cursing Castro could control his own habit, while the loss of Cuba remained beyond his control.

The Assassination Plot and Its Record

Castro’s conflict with organized crime also enters the account through later investigations of U.S. dealings with the mob. In June 1975, amid the Church Committee’s Senate hearings on the U.S. Central Intelligence Agency’s ties to organized crime, Time magazine reported that Bufalino’s assistance had been recruited for a mysterious plot against Castro. The account dates the alleged scheme to just before the April 1961 Bay of Pigs invasion and describes poison pills as its intended means of assassination.

The Church Committee concluded that Bufalino had been part of the conspiracy. This is not evidence of Castro’s participation in the plot, but of the way his removal of mob assets helped make him a target in a broader nexus of political and criminal activity. The episode also shifts the account beyond private grievance: Castro’s confrontation with the mob is linked to covert state action, while the committee’s findings turn a once-secret scheme into a matter of public record.

Narrative Role and Limits

Castro is defined here less through personal characterization than through consequences. His government’s seizure of casinos and expulsion of mob figures altered the financial landscape described elsewhere in the account, where Havana casinos appear among ventures supported by Teamsters pension-fund loans. The same revolution that ended those Cuban holdings thus shadows a wider story of organized crime seeking capital and influence beyond the island.

The evidence is uneven in kind. Sheeran’s account supplies the boat, the curses, and the wager, but explicitly presents some details as hearsay; the later account invokes contemporary reporting and the Church Committee’s conclusion. Taken together, these perspectives make Castro a force at the edge of the narrative: absent from its personal scenes, yet consequential enough to provoke a durable grievance and become the target of an alleged assassination conspiracy.