Havana

On Christmas Eve, 1958, Roberta Duran asks Jack Weil to help smuggle radios for the revolutionaries aboard the Miami-to-Havana crossing. Weil agrees to the plan because he is romantically drawn to Roberta. The request sets in motion a dangerous operation that threads through the rest of the story.

Weil commits to assisting Roberta’s cause, driven by his growing attraction. He accepts the risk to his gambling livelihood and personal safety as they begin to plan the smuggling operation. The alliance marks the start of a complicated romance entangled with politics.

After arriving in Havana, Weil runs into Roberta and her husband, Dr. Arturo Duran, during a night on the town. Duran asks Weil for further aid for the revolution; Weil initially refuses, wary of dangerous entanglements. The encounter foreshadows the tensions to come.

Roberta reveals she is married, which shatters Weil's idealized pursuit of a simple romance. The disclosure complicates their relationship and raises the stakes of their political collaboration. Havana's nightlife and the revolution’s undercurrents continue to press in.

Following a night of debauchery, Weil reads a newspaper account of Duran’s arrest and death. He is stunned to learn Roberta was arrested and tortured in custody. He uses his influence with another debt-holder to secure her release, escalating his involvement.

Shaken by her husband’s death and her own jail ordeal, Roberta seeks shelter in Weil’s apartment. She vanishes later that afternoon, leaving Weil anxious and more determined to find her. The disappearance deepens the emotional stakes and the mystery surrounding her.

Weil, now in love and encouraged by a gambling friend, travels into Cuba’s interior to locate Roberta at Duran’s old estate. He persuades her to return with him to Havana and to consider leaving Cuba together. The rescue mission becomes a turning point in their relationship.

Weil checks with Marion Chigwell, a CIA acquaintance, who confirms that Duran is still alive. He pressures Chigwell to help free Duran, weaving a web of deception that pretends CIA involvement. This alliance strengthens Weil’s leverage against the regime.

Pretending to work for the CIA, Weil visits Duran, held by the chief of the secret police. He claims Washington wants Duran released and plans to pay a $50,000 payoff to secure his freedom. The scheme hinges on manipulation and the fragile line between ally and coercion.

Weil hurries to a doctor and then a jeweler to extract money from the diamond hidden in his arm, in order to raise the ransom for Duran’s release. He reveals to Roberta that her husband is alive, shocking her and prompting her to go in search of him. The revelation intensifies the emotional stakes and the race against time.

Weil bets big in the casino to fund the rescue plan, but he loses the high-stakes game. Joe Volpi, the casino’s manager, forgives him, recognizing that Weil’s priority is saving Roberta, even if it costs him personally. The loss is a setback that tests his resolve.

On New Year’s Eve, 1959, the revolution has won and the elite scramble to flee Cuba. The streets erupt with celebration as casinos are trashed and the people embrace the change. Weil and Volpi decide it’s time to leave, seeking safety as the regime changes hands.

The next morning, Weil sits in a Havana restaurant preparing to depart when Chigwell arrives with news of a new book project. Roberta appears to bid him farewell and notices the bandage on Weil’s arm, understanding the cost of saving her husband. She chooses to stay with the revolution, and Weil is forever changed by the experience.

Four years later, in 1963, Jack drives down to the Florida Keys and gazes toward Havana, hoping to see a boat bringing Roberta. He knows the ferry no longer runs, but he performs this yearly vigil as an echo of the changes in Cuba reverberating through the United States. The ritual underscores the lasting costs of love and revolution.