Prohibition

Prohibition is recalled not through a scene set in the period itself, but as a political precedent invoked decades later. At a 1961 dinner, Russell Bufalino connected the elder Kennedy’s alleged profits from scotch brought into the country with the influence the Kennedy family was said to wield over national politics. The recollection gives Prohibition a place in the book’s account of how criminal wealth, political access, and expectations of reciprocal favors became entangled.

The 1961 recollection

Frank Sheeran recalls dining alone with Russell Bufalino at Cous’ Little Italy restaurant in Philadelphia, a few weeks after the Christmas party and before Easter. The conversation turned to President Kennedy and what he might do about Cuba. Bufalino said that during Prohibition the elder Kennedy had made money on every bottle of scotch entering the country. He further claimed that the elder Kennedy controlled the president and was expected to secure government help for the mob’s interests in Cuba and to end the McClellan hearings.

The account presents Prohibition through Bufalino’s assertion, not as a separately documented episode. Its emphasis is on the lasting political value he assigns to wealth accumulated during that earlier period: the alleged profits matter because, in his telling, they created leverage that could later be called upon.

From past profits to expected favors

Sheeran’s retrospective interpretation extends Bufalino’s claim. He speculates that the elder Kennedy may have encouraged President Kennedy to proceed on Cuba to repay Sam Giancana for help in the election. In this reading, support for recovering casinos, racetracks, and other businesses in Cuba could function like a political favor returned in kind. The proposed chain runs from Prohibition-era income, through family influence, to an anticipated benefit for mob figures in the 1960s; the book marks the final link as Sheeran’s later inference, not established fact.

Narrative significance

The brief reference makes Prohibition a remembered origin point for a larger story about influence. It is raised during a conversation about Cuba and the pressure of the McClellan hearings, so the past is made relevant by what Bufalino believes it can still purchase. The period appears less as a self-contained historical setting than as an explanation offered within a network of favors, business interests, and political expectations. Its force rests on that distinction: the narrative records what Bufalino claimed and what Sheeran later inferred, while leaving those claims attributed to their speakers.