On September 18, 1960, four months before the U.S. severed diplomatic relations with Cuba and 56 years before Barack Obama would become the first sitting American president in almost a century to step foot on Cuban soil, Fidel Castro arrived in New York City for the 15th session of the United Nations General Assembly.

Castro had taken in the Big Apple the previous year, fresh off the successful overthrow of U.S.-backed dictator Fulgencio Batista. He ate ice cream at the Bronx Zoo, and posed for smiling pictures with blond-haired children. Wherever he showed his scraggly bearded face, from Yankees Stadium to the New York Press Photographer’s Ball, the fatigue-clad prime minister was fawned over like a celebrity—even as animosities between his young revolutionary government and the great superpower to the north were already starting to reach a breaking point.

The reception that awaited him the following fall wasn’t nearly so warm. Castro and his bohemian entourage got off to a bad start with management at the elite Shelbourne Hotel, which allegedly demanded an exorbitant advance ahead of the Cuban delegation’s stay. Soon, New York tabloids were circulating reports that these “uncouth primitives” had “killed, plucked, and cooked chickens in their rooms at the Shelbourne and extinguished cigars on expensive carpets.” One subsequent Cuban defector later claimed that Castro had staged the drama. In any case, the Cubans left the Shelbourne, checking in instead at the Hotel Theresa, up past 124th Street in Harlem.

Castro’s decision to relocate his contingent to the heart of black New York quickened the falling out to come and presaged key pillars of Cuban foreign policy over the course of the next half-century: the explicit conflation of Cuban sovereignty with worldwide liberation struggles, particularly in Africa, and the strategic leveraging of U.S. moral hypocrisy in service of revolutionary ideology. Ploy or not, writes historian Brenda Gayle Plummer, the move “constituted a watershed” in U.S.-Cuban diplomacy, “not only because it coincided with a critical juncture in the history of U.S. race relations, but also because it marked a departure in conventional ways of perceiving, and prosecuting, the Cold War.”

To understand what it means for Barack Obama to walk the streets of Havana after all these years, it’s worth recognizing what it meant for Fidel Castro to set up shop in Harlem. ...