Havana

Roberta Duran asks Jack Weil to help smuggle radios for Cuban revolutionaries aboard the Miami to Havana crossing. Weil agrees, drawn to her romantically even as he understands the mission's danger. The pact sparks a fragile alliance that threads through the explosive events to come.

Upon arriving in Havana, Weil encounters a Cuban journalist acquaintance, and during a night on the town they unexpectedly run into Roberta and her husband Arturo Duran. Duran asks Weil for continued aid to the cause, testing his loyalty. Weil declines, setting the stage for later tension.

After a night of revelry, Weil reads a newspaper report that Arturo Duran has been arrested and killed. The shock pulls him into the underworld of the city as he learns Roberta has also been arrested and tortured. The personal stakes suddenly dwarf his earlier plans.

Weil engineers the release of Roberta by pressuring a fellow debtor to help, though the rescue is precarious. She is sheltered in his apartment, but she vanishes that afternoon, leaving Weil unsettled and more determined to find her. The events dramatize the cost of love and the risks of rebellion.

Realizing he is in love with Roberta, Weil, spurred by an old gambling friend, travels deep into Cuba to locate her at Arturo Duran's former estate. He persuades her to return with him to Havana and to consider leaving the country. He reveals a diamond in his arm that he carries as a personal insurance in case of need.

Two Cuban men intercept Weil's return and inform him that Duran demands Roberta be taken out of the country. Weil then enlists Marion Chigwell, a CIA acquaintance, who confirms that Duran is alive and pushes him to help. He pressures Chigwell to cooperate in freeing Duran.

Posing as a CIA operative, Weil visits Duran, who is being held by the chief of the secret police. He tells the chief that Washington wants Duran released for a payoff of $50,000. He funds the bribe by selling the diamond, visiting a doctor and a jeweler. He also tells Roberta that her husband is alive, prompting her to leave to find him.

Weil shifts his focus to the casino, pulling off a big gamble that tests his nerves and finances. Joe Volpi, the casino manager, forgives him, understanding that his priority is saving Roberta rather than profit. The line between gambling risk and personal rescue blurs on the floor.

On New Year’s Eve, 1959, the revolutionaries win and Havana erupts in celebration as the old order scrambles to flee. The upper class abandons their luxury while the people trash the casinos in a spontaneous show of power. Weil and Volpi decide it is time to leave, even as their personal story remains unresolved.

The next morning, Weil sits in a Havana restaurant preparing to depart when Roberta appears to bid him farewell. She sees the bandage on his arm and realizes the price he paid to save her husband. She chooses to stay with the revolution, and Weil is forever changed by the ordeal.

Four years later, in 1963, Jack drives to the Florida Keys and gazes toward Havana, hoping to glimpse a boat bringing Roberta. He knows the ferry no longer runs, yet he keeps the annual vigil as a symbol of longing and of Cuba's shifting fate. He recognizes that changes in Cuba are echoed in the United States.

Roberta remains with the revolution, while Weil's experiences have left him a changed man. The ending underscores the collision of personal longing with political upheaval and hints that some bonds survive only in memory.