On Christmas Eve, 1958, aboard the boat from Miami to Havana, Roberta Duran [Lena Olin] enlists the aid of Jack Weil [Robert Redford] to smuggle radios for the revolutionaries in the hills. Weil agrees only because he is romantically drawn to her, and a fragile spark of feeling threads through their uneasy alliance. When they rendezvous for the payoff, Roberta reveals that she is married, cooling Weil’s hopes and adding a complication to their already perilous task.
In Havana, Weil encounters a Cuban journalist acquaintance, and during a night on the town they run into Roberta and her husband, Dr. Arturo Duran [Raúl Juliá], a revolutionary leader. Duran asks Weil for further aid for the cause, testing Weil’s loyalties and boundaries. Weil, feeling the weight of his conscience, turns him down and tries to walk away from the escalating danger, even as the revolution tightens its grip on the city and the couple’s fates become entwined with his own.
After a night of debauchery, Weil reads a newspaper account of Duran’s arrest and death. In shock, he continues with the planned poker game, coincidentally meeting the head of the secret police. He learns that Roberta was arrested and tortured in custody. He pressures another player in debt to him to obtain her release and, upon learning of the suffering she endured, he makes a personal vow to shelter her. Shaken by her husband’s fate and her jail ordeal, she lets him shelter her in his apartment, but she disappears that afternoon, leaving Weil to grapple with a growing sense of responsibility he cannot easily shake.
Realizing that he is in love with Roberta and encouraged by an old gambling friend, Weil drives into Cuba’s interior to find her at Duran’s old estate. He persuades her to return with him to Havana and to leave Cuba with him. When she asks, he explains that a lump on his arm contains a diamond he had planted there in his youth as insurance, a symbol of the risks he is willing to take for their future. He makes arrangements for her to leave Cuba via boat, but on his return to the apartment, he is assaulted by two Cubans, who inform him that Duran demands he get Roberta out of the country nonetheless.
Weil has a CIA acquaintance, Marion Chigwell [Daniel Davis], who confirms that Duran is still alive. He intimidates Chigwell into working with him to free Duran, a dangerous alliance built on deception and faith in a distant, changing future. Pretending to work for the CIA, Weil goes to see Duran, who is being held by the chief of the secret police. He tells the chief that Washington has plans for Duran and wants him released, with a payoff of $50,000. Weil goes to a doctor and then a jeweler to sell the diamond to raise the bribe for Duran’s release. He tells Roberta, who had decided to make a life with him, that her husband is alive. In shock, she leaves on her own to find her husband, while Weil’s own fortunes swing between risk and resolve.
Meanwhile, Weil blows the big game with high rollers, for whom he had been angling since he arrived in Havana. The casino’s manager, Joe Volpi, forgives him, understanding that Weil has chosen to prioritize Roberta’s safety and Duran’s fate over personal glory. On New Year’s Eve, 1959, the revolutionaries have won, and the city erupts in a wild, celebratory upheaval as the upper class and the secret police scramble to escape. The streets fill with revelers who trash the casinos and dance in the glow of a seismic political shift.
The next morning, Weil is in a restaurant preparing to depart. He sees Marion Chigwell, who informs him that he is working on a new book, The Cuisine of Indochina, and the encounter underscores the strange disjunction between his dangerous past and an uncertain future. Roberta shows up to bid him farewell. She sees the bandage on his arm and understands what it cost him to save her husband for her. She chooses to stay with the revolution, and Weil is left transformed by what he has learned and what he has lost.
Four years later, in 1963, Jack drives down to the Florida Keys and gazes across the sea toward Havana, hoping to see a boat bringing Roberta. He knows the ferry is no longer running, yet he keeps faith with the impossible dream, returning to the same vigil each year. He also realizes that the changes roiling Cuba are echoing across the United States, shaping not only a country’s fate but the inner life of a man who took extraordinary risks for love, loyalty, and a cause larger than himself.
