In 1958, agents from Cuban President Fulgencio Batista’s Servicio de Inteligencia Militar (SIM) board an American ship moored in Havana. When they threaten to create problems because of an unregistered gun, professional gambler Jack Weil claims ownership and pays a bribe. Returning to the party, Jack extracts a payment from the gun’s Cuban owner, who would have been arrested if Jack had not intervened. Roberta “Bobby” Durand, a Swedish-born American citizen, offers Jack $600 to drive her automobile off the ship. Inside the car, Jack finds U.S. Army portable radios behind door panels, but nonetheless drives through customs to Havana’s Lido casino. He talks briefly with Cuban reporter Julio Ramos, who warns that the Communist revolution in the hinterlands is nearing Havana. Lido manager Joe Volpi welcomes the American back to Havana, and Jack suggests organizing a big poker game. While Joe is convinced that fear of revolution has dampened business, Jack disagrees, claiming that uncertainty excites gamblers. Jack meets Bobby to complete their transaction, and calls her a dilettante playing at being a revolutionary. Bobby responds that Jack is arrogant and knows nothing about Cuba beyond Havana. Jack goes to another casino and starts a poker game that draws several “high-rollers” and a large crowd, prompting Joe Volpi to agree to let Jack host a similar game at the Lido, financed by Joe’s boss, mobster Meyer Lansky. All his life Jack has wanted to play “the big game,” and now he has found the perfect time and city. Later, Jack discusses the revolution with Julio Ramos and a man named Marion Chigwell, a Gourmet magazine food writer. Jack and Julio join two female American tourists and take them to dinner at a restaurant. Julio is shocked to see that Arturo Durand, a wealthy Cuban revolutionary wanted by SIM, is there. Jack is surprised to see Arturo accompanied by Bobby Durand. The couple approach Jack, and Arturo thanks him for helping his wife, then furtively returns the money she paid him by slipping it into her purse. Arturo recognizes that Jack is unaware of Cuba’s inequity under the corrupt Batista regime, but hopes someday he will become an ally. Arturo and Bobby are called away to meet with members of the resistance, and after Julio passes out from drinking, Jack accompanies the two tourists to their hotel for a night of sex. In the early morning, SIM arrests local revolutionaries, including the Durands. Later, as Jack drinks coffee at a café, Julio shows him a newspaper announcing Arturo’s death. Meanwhile, Colonel Menocal, head of SIM, personally oversees an officer pushing Bobby’s head into a bucket of water to extract information. At one point, through a partly closed door, Bobby sees one of Arturo’s intimates, Bufano, speaking with the colonel and betraying his comrades. A corporal shows Bobby the battered body of a young female revolutionary, who Bobby praises, stating that she will confess nothing. Meanwhile, Joe Volpi sets up a card game with several players, including a Cuban lieutenant and Col. Menocal. As the game begins, Jack “innocently” asks the colonel if Mrs. Durand is still alive. The table goes quiet. Early the next morning, after Jack defeats Menocal in the final hand of the game, the colonel congratulates Jack and mentions that “Mrs. Durand is being questioned.” Although the lieutenant lost badly, Jack forgives the debt and gives the soldier airline tickets to Miami, Florida, along with $2,000, in exchange for Bobby’s release. Jack takes her to an apartment he keeps in Havana, and offers to fly her to America. Exhausted from their long night, Bobby and Jack go to sleep, but he later awakens to find her gone. Suddenly, Col. Menocal and a SIM agent burst through the door and search for Bobby. The colonel returns the airline tickets Jack gave the Cuban lieutenant and warns him against helping traitors. At a party at the Lido, Julio tells Jack he is flying to Miami because the SIM has shut down his newspaper. Chigwell becomes agitated after Jack tells him Bobby has been released. Afterward, Jack sees Chigwell berating Col. Menocal. In Joe Volpi’s office, as a radio announcer broadcasts fighting in the Cuban city of Santa Clara, Joe informs Jack that the rebels have “cut the island in half.” Meyer Lansky enters and tells Joe to order President Batista to destroy the rebels, or he will find someone else to do it. During a walk through the city with Jack, Joe laments that he is no longer an American citizen because of his involvement with organized crime, so he will stay in Cuba until the end, then perhaps start over with Lansky in another Caribbean country. The next day, Jack visits his aging gambling mentor, the “Professor,” talks about Bobby, and expresses his uncertainty about staying in Cuba. The Professor suggests he follow his heart and pursue a relationship with Bobby. Jack drives 200 miles south to Santa Clara and finds himself in a war zone. A village has been destroyed, and its inhabitants hanged and shot. Eventually, a boy leads Jack to Bobby. He pleads with her to leave Cuba, but she chides him for not believing in anything but his own comfort. After several rebels visit the house to privately confer with Bobby, Jack insists she cannot “live ideas,” but she claims she loves being part of something bigger than herself. Despite Jack’s cynicism, he confesses that Bobby has changed his world. They return to Havana and make love in Jack’s apartment. Afterward, Bobby notices a scar on his arm, and he explains that his mentor had a diamond sewed into his arm, so he would always have “a last chance,” and Jack did the same. When Jack returns to the Lido, Joe tells him the poker game is set for that evening. Jack meets with the captain of a small boat and pays him to have it ready to leave at midnight. Returning to his apartment, Jack is assaulted by two men, who tell him Arturo Durand wants Bobby out of Havana the next day. Jack informs Bobby that they will leave the island at midnight, but she cannot go home to pack. Returning to the Lido, Jack spots Chigwell at the busy casino and asks if Arturo is still alive. When Jack threatens to expose Chigwell as a member of the Central Intelligence Agency (CIA), Chigwell reveals that Col. Menocal works for both SIM and the CIA. Jack drives to Col. Menocal’s estate, tells him Chigwell is offering him asylum in America, and demands to see Arturo Durand. Angry at Chigwell’s betrayal, the colonel explains that America pays him to keep Communists under control, and he resents the CIA wanting to spare one of them. His men take Jack to Arturo’s cell, and the revolutionary thanks Jack for seducing his wife, because his hatred for Jack kept him alive. Meanwhile, the card game begins at the Lido. After arranging for Menocal to take Arturo to the boat, Jack returns for Bobby. She is excited about her new life with Jack, but when he informs her that Arturo is alive and waiting for her, she slaps him, leaves his apartment, and returns home. Gunshots are heard outside the city, government officials are fleeing the country, and revelers celebrate the end of the Batista regime. Jack hurries to the Lido and tells Joe Volpi that Bobby has rejoined her husband. A crowd smashes through the doors and wrecks the casino, while others rush to the harbor, hoping to escape. The next morning, at a seaside restaurant, Chigwell tells Jack that the colonel left Cuba the previous night, and Chigwell himself is off to Indochina. Now that Bobby and Arturo no longer have to flee Cuba, she asks Jack where he plans to go. He says California, and she notices a bandage over the place on his arm where the diamond was embedded. Jack declares his love for her, but accepts his fate. They embrace and say goodbye. Five years later, in 1963, Jack drives to Key West, Florida. The ferry between Key West and Communist Cuba no longer operates, but he anticipates Bobby’s arrival, because sometimes boats are blown off-course, and “this is hurricane country.”