What Is Havana About?
The premise of Havana in 329 words, with nothing given away. The full story follows below.
In the fever‑dream of late‑1950s Havana, a city teeters between decadence and upheaval. Neon signs flicker over bustling cafés while the streets pulse with whispered rumors of an impending revolution. The air is thick with cigar smoke, salt from the harbor, and the restless energy of a society on the brink of transformation. Within this vibrant, volatile backdrop, the glitter of high‑stakes casino tables offers a fleeting refuge for those willing to gamble with more than just money.
Jack Weil arrives in the capital with a reputation for mistrust and a talent for reading opponents across a felt surface. A seasoned high‑roller accustomed to the cut‑throat world of professional poker, he carries the weight of past cons and the constant itch for the next perfect hand. The city’s casinos become his stage, where every bet is a negotiation with fate and every glance across the table a test of resolve. His guarded nature masks a lingering yearning for something—perhaps redemption or a chance to prove his worth—that goes beyond the usual chase of chips and cash.
Roberta Duran steps onto this scene as a striking, daring presence whose own stakes are far more precarious. Married to a man deeply entangled in the revolutionary cause, she navigates the dangerous overlap of personal loyalty and political conviction. Their paths cross against the roar of clinking glasses and the hushed tension of secret deals, sparking an unexpected and volatile attraction that threatens to upend both of their carefully constructed facades. The chemistry between them crackles amid the chaotic rhythm of a city where love, danger, and ambition are inextricably linked.
Amid the looming promise of change, the narrative swirls with smoky intrigue, intoxicating romance, and the relentless pull of risk. The characters move through a world that doubles as a playground for fortune‑seekers and a crucible for revolutionaries, leaving the audience to wonder how far each will go when the line between personal desire and the tides of history begins to blur.
What Happens in Havana?
The complete story of Havana, from the first scene to the last, in 789 words (about 3 minutes). Spoilers throughout.
Spoilers ahead
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.
Havana Timeline: Every Key Event in Order
14 key events in the order they happen, from “Roberta enlists Weil to smuggle radios from Miami to Havana” to “Four years later; 1963; Weil’s annual vigil in the Florida Keys”. 14 events name a place, across 9 locations.
- 1
Roberta enlists Weil to smuggle radios from Miami to 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.
When:Christmas Eve, 1958 Where:On a boat from Miami to Havana
- 2
Weil agrees to help because of his romance with Roberta
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.
When:Christmas Eve, 1958 Where:On a boat from Miami to Havana
- 3
In Havana, Weil meets a Cuban journalist; encounter with Roberta and Duran
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.
When:Late 1958 Where:Havana
- 4
Roberta's marriage revealed; Weil's hopes dashed
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.
When:Late 1958 Where:Havana
- 5
Duran's arrest and Roberta's arrest; Weil acts
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.
When:Early 1959 Where:Havana
- 6
Roberta shelters with Weil; disappears
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.
When:Early 1959 Where:Weil's apartment, Havana
- 7
Weil falls in love and ventures into Cuba's interior to find Roberta
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.
When:Early 1959 Where:Duran's old estate, interior Cuba
- 8
Chigwell confirms Duran is alive and contributes to the plan
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.
When:Early 1959 Where:Cuba
- 9
Weil confronts the secret police; plans a release through bribery
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.
When:Late 1958 / Early 1959 Where:Secret police headquarters
- 10
Weil sells the diamond to fund the bribe; Roberta learns the truth about her husband
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.
When:Late 1958 / Early 1959 Where:Havana
Show the other 4 events of Havana Hide the last 4 events
- 11
Weil loses the big casino game; Volpi forgives him
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.
When:Late 1958 / Early 1959 Where:Havana casino
- 12
New Year's Eve 1959; revolutionaries triumph; the exodus begins
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.
When:New Year’s Eve, 1959 Where:Havana
- 13
The morning after; Roberta chooses the revolution; Weil is changed
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.
When:January 1, 1960 Where:Havana restaurant
- 14
Four years later; 1963; Weil’s annual vigil in the Florida Keys
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.
When:1963 Where:Florida Keys
Who Are the Main Characters in Havana?
6 characters, among them Jack Weil (Robert Redford), Roberta Duran (Lena Olin) and Arturo Duran (uncredited) (Ral Juliá): who each one is and the part they play in the story. Every profile links to the actor’s page.
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Jack Weil (Robert Redford)
Played by Robert Redford
A sharp, charming American gambler who navigates Havana’s casino world with improvisational wit. He becomes entwined with Roberta’s mission to aid the revolution, agreeing to help only out of romantic interest. Throughout the story he risks wealth and safety, undergoing a personal transformation shaped by the upheaval.
- 🎭 Charismatic
- 🎲 Gambler
- ❤️ Romantic
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Roberta Duran (Lena Olin)
Played by Lena Olin
A determined Cuban-American woman drawn into the revolutionary cause through personal ties and danger. Her romance with Weil complicates loyalties as she navigates arrest, torture, and shifting allegiances. She ultimately chooses to stay with the revolution and follow her husband’s fate.
- 🎭 Determined
- ❤️ Love
- 🧭 Conflicted
- AD
Arturo Duran (uncredited) (Ral Juliá)
Played by Raúl Juliá
A Cuban revolutionary leader and Roberta’s husband whose fate drives much of the plot’s urgency. He is arrested and presumed dead in a newspaper account, later revealed to be alive, complicating Weil’s efforts to rescue him. He embodies the personal cost within the broader political struggle.
- 🔥 Revolutionary
- 🎭 Husband
- 🧭 Strategic
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Joe Volpi (Tony Plana)
Played by Tony Plana
The Havana casino boss whose operations intersect with Weil’s schemes. He forgives Weil’s big night of gambling, understanding the rescue of Roberta as worth more than the payoff. He embodies the pragmatic, morally flexible side of the casino world.
- 🎰 Casino
- 🏦 Leader
- 🧭 Opportunist
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Marion Chigwell (Richard Portnow)
Played by Richard Portnow
An American CIA contact who shuttles information and legitimacy between Weil and the Cuban players. She becomes entangled in the rescue plan, pressing Weil to act while masking her own agenda. Her involvement underscores the international dimensions of the intrigue.
- 🕵️♀️ Agent
- 🎭 Ally
- 🧭 Strategist
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Meyer Lansky (Mark Rydell)
Played by Mark Rydell
A real-life figure depicted as a key influence in Havana’s casino ecosystem. His presence signals the entwinement of crime, politics, and international finance in the city’s underworld. His role underscores the era’s murky power dynamics that shape the plot.
- 💼 Financier
- 🎭 Historical Figure
- 🧭 Influential
Where and When Is Havana Set?
Havana is set in Miami, Havana and Cuba (1958-1963). Here is why the time and place matter to the story.
When
1958-1963
The action begins on Christmas Eve 1958 as the island teeters on the brink of revolution. It culminates with the revolution's victory on New Year’s Eve 1959 and later follows events four years on in 1963 along the Florida Keys, as Weil eyes Havana from afar.
Where
Miami, Havana, Cuba
Set across Miami and Havana, the story moves from a bustling port to the glittering casino scene of Havana. The Cuban capital is depicted as a playground for wealth, power, and political intrigue on the cusp of revolution. The places serve as stages for gambling, espionage, and romance that drive the plot.
- 🌊 Coastal
- 🏙️ Urban
- 🗺️ Historic
What Are the Themes of Havana?
3 ideas the story keeps returning to, among them Romance, Revolution and Gambling.
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01
Romance
A central romance threads through Weil and Roberta, influencing risky decisions and blurring lines between personal desire and political obligation. Weil pursues Roberta, risking his own safety to protect her and the revolution’s broader aims. The romance shapes key choices, including sheltering her and planning an escape.
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02
Revolution
The Cuban upheaval frames the entire narrative, turning casinos, crime networks, and expatriates into chess pieces. The fall of Batista’s regime and the escape rush reveal how quickly society can transform when political power shifts. Characters confront loyalties as the old order expires and a new Cuba emerges.
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03
Gambling
Gambling is not just a business but a metaphor for risk, deception, and leverage. Weil’s poker games and the diamond-as-insurance drive the plot and expose the moral costs of chasing fortune. The casino world tests characters’ nerve, trust, and capacity to sacrifice for others.
What Kind of Film Is Havana?
Melancholic in tone, with steady pacing and a moderate story, going by the plot summary.
- Tone
- Melancholic
- Pacing
- Steady
- Story
- Moderate
- Intensity
- High
- Ending
- Bittersweet
A tense and melancholic romantic drama set against the backdrop of a violent revolution, where a cynical man's dangerous passion for a committed revolutionary leads to profound personal sacrifice and a bittersweet sense of loss.
- romantic
- tense
- melancholic
- atmospheric
- urgent
- passionate
- political revolution
- ill-fated romance
- personal sacrifice
- moral ambiguity
Content notes: torture, political violence, imprisonment.
Quiz
How well do you remember Havana? Test yourself on the story.
