John F. Kennedy

John F. Kennedy is a consequential but largely offstage figure in the book: his presidential campaign becomes a point of division among powerful underworld allies, his administration’s actions reshape Jimmy Hoffa’s fortunes, and his assassination prompts new suspicions about organized crime. The account does not give Kennedy an interior voice. It constructs his role through Frank Sheeran’s recollections, reported conversations among mob figures, and the political consequences that followed.

Political Context and the 1960 Campaign

Sheeran places Kennedy’s candidacy within the conversations he says he witnessed among Hoffa and Sam Giancana. Giancana expected Kennedy to help remove Fidel Castro and restore the casinos and other valuable interests that the Cuban revolution had taken from mob figures. He also said that Kennedy’s father had promised that, if his son won, Robert F. Kennedy could be controlled and would pose no threat. Sheeran’s account describes the elder Kennedy as a former bootlegger who had brought whiskey through Canada and maintained connections with Italian associates as he moved into more legitimate ventures. These claims enter the narrative as part of what Giancana told Hoffa, not as independently established evidence about the Kennedy family.

Giancana said he would help Kennedy against Richard Nixon and claimed he could arrange the outcome in Illinois. Hoffa, according to Sheeran, was astonished by the proposal and tried to dissuade Giancana. Hoffa doubted that the Kennedys would help organized crime regain Cuba and regarded their trustworthiness with suspicion, recalling the government’s treatment of him during the McClellan Committee hearings. He believed Nixon would defeat Kennedy and was more likely to assist them in Cuba. The disagreement exposed a political calculation within the mob network: Giancana saw a possible route back to lost assets, while Hoffa thought the promised alliance was dangerous and misplaced.

The Presidency, Organized Crime, and Cuba

Kennedy won the presidency by a narrow margin. The book emphasizes the sharp reversal that followed: he appointed his brother attorney general, placing Robert F. Kennedy over the Justice Department, the United States attorneys, and the Federal Bureau of Investigation. Robert F. Kennedy then turned the department toward organized crime, forming a team of lawyers and investigators under Walter Sheridan. Its deliberately pointed name was the Get Hoffa Squad. In the book’s account, Kennedy’s election therefore did not deliver the protection that Giancana had anticipated. Instead, the new administration intensified the pressure on Hoffa and his circle.

The failed Bay of Pigs invasion further discredited the prospect of a Kennedy-led recovery of Cuba in Sheeran’s telling. He recalls hearing in April that Kennedy had withheld American air cover from the amphibious force. The anti-Castro fighters, he says, had no ships offshore to bombard the land above the beachhead; those not killed were captured. Sheeran’s account presents the result as a military disaster and as another reason for the mob figures to resent the administration. The Cuban question was not simply a foreign-policy issue in these conversations: it concerned casinos, property, and the power of men who had been driven from the island.

Sheeran also describes later reports of alleged mob plots to assassinate Castro, but he distinguishes those reports from what he says he personally witnessed. He recalls driving with Russell Bufalino to meetings at Joe Sonken’s Gold Coast Lounge in Florida, where Santo Trafficante and Carlos Marcello sometimes met. He says he never heard anyone there, including Bufalino, discuss a plot with the Kennedy government to kill Castro by poison or bullet. The difference matters in the narrative: it records both the later public allegations and the limits of Sheeran’s claimed knowledge, without establishing that Kennedy participated in such a plan.

Assassination and Suspicion

On November 22, 1963, Kennedy was assassinated in Dallas. Sheeran recalls hearing the news on the radio while visiting the union hall in Wilmington, Delaware, on union business. He says the killing troubled him, although Kennedy had not been one of his favorite politicians and he had no personal grievance against him. Before Lee Harvey Oswald was killed by Jack Ruby, Sheeran says, he wondered whether the assassination might be connected to an earlier matter at Monte’s Restaurant. He also says there was nobody he could ask. His recollection captures the atmosphere of suspicion surrounding the murder without supplying evidence that resolves it.

The book also reports that Robert F. Kennedy privately considered whether Oswald had acted alone or as part of a larger conspiracy involving Castro or gangsters. Two years after the Warren Commission issued its report, Robert F. Kennedy reportedly told Richard Goodwin that he had never thought the Cubans were responsible and that, if anyone else was involved, he suspected organized crime, though he could do nothing about it then. This is presented as Robert F. Kennedy’s private assessment, not proof of a mob role in the assassination. The narrative further stresses that he understood the danger of acting against organized crime without evidence or a broader political opening.

Narrative Role and Legacy

Kennedy’s importance in the book lies in the chain of expectations and reversals attached to his name. Before his election, Giancana imagined that a Kennedy victory could help reclaim Cuba, while Hoffa warned against trusting that promise. Once Kennedy became president, Robert F. Kennedy’s appointment and anti-crime campaign transformed the federal government into an active adversary of Hoffa. Kennedy’s death then redirected attention toward possible political and criminal conspiracies, including the question of whether organized crime had been involved.

The portrait remains mediated and qualified. Kennedy is encountered through what Sheeran says mob leaders believed, what the administration did, and what Robert F. Kennedy later suspected. The account does not confirm the criminal allegations surrounding the Cuban plots or the presidential assassination. Instead, it shows how Kennedy’s election, policies, and death became entangled with the ambitions, fears, and rivalries of the men whose world the book examines.