Plot summary

In December 1958, former British military officer and counter-insurgency specialist, Major Robert Dapes (Sean Connery), arrives in Havana, Cuba, as a mercenary. He has been hired by General Bello (Martin Balsam) on behalf of the military dictator General Fulgencio Batista (Wolfe Morris) to help the Cuban army defeat Fidel Castro's rebellion. Arriving on the same flight is American investor, Larry Gutman (Jack Weston), who is met outside the terminal by elegant businesswoman, Alexandra Pulido (Brooke Adams). Passing by, Robert thinks he recognizes her as a former lover, but her chauffeured car drives away as he calls out to her. Captain Ramirez (Hector Elizondo), Robert's military escort, informs him that she is married to a member of Cuba's oldest and wealthiest families, the Pulidos.From the airport, Alexandra takes Gutman to the cigar factory she manages. In her absence, Juan Pulido (Chris Sarandon), Alexandra's philandering husband, is involved in a continuing his affair with factory worker Therese Mederos (Lonette McKee), and when Alexandra returns to the office, she notices a flirtatious exchange between them. While Juan escorts Gutman through the plant, Alexandra fires Therese. To impress Gutman, Juan shows him the scope of his family's business, encompassing tobacco, sugar, and rum, and then introduces him to his father, the tycoon Don Jose Pulido (Walter Gotell). Don Jose informs Gutman that his daughter-in-law Alexandra is the real executive of the cigar factory while his son Juan would rather be a playboy. When Alexandra announces that she dismissed Therese, Juan appears unconcerned and promises to refrain from dallying with the staff. Gutman then leaves and meets with British executive Donald Skinner (Denholm Elliott) who is looking for Gutman's representation to buy up more sugar field land in Cuba to open a sugar factory.Meanwhile, Ramirez takes Robert to a luxurious, modern hotel, but Robert chooses to stay in less conspicuous, modest accommodations at a local seedy hotel. After settling in, Robert meets with General Bello and emphasizes that strategy rather than weapons will subdue the rebels. As the general grants him exclusive security clearance, Robert warns Bello that Castro will be difficult to defeat if the people are on his side.While visiting a military barracks, Robert sees the woman from the airport again and realizes that she is "Alex." Robert interrupts her tennis game to say hello, but she discourages his greeting, stating that she is married now.During a reconnaissance patrol, Robert helps capture a rebel soldier as well as enemy documents. Despite this small gain, Ramirez tells Robert that he might have arrived too late to help the Cuban army win the larger battle.That evening, the rebels ambush a formal dinner party hosted by General Bello and kill several high-society guests. Robert and Ramirez arrive immediately after the shooting and assist the wounded until ambulances arrive.Elsewhere in the city, Julio Mederos (Danny De La Paz), an ambitious young teenage rebel fighter, prepares to kill Juan Pulido for betraying his sister, Therese, but she tries to dissuade her brother. Meanwhile, at the Flamingo nightclub during a Christmas Eve party, Alexandra is angry with Juan for assuming that she would share a table with Gutman's companion, a prostitute. When Robert arrives, she joins him at the bar, recalling fond memories of their passionate affair 15 years ago. Robert is about to warn her of the recent massacre, but is interrupted by Juan's appearance. As Alexandra introduces the two men, Robert notices Julio aiming a gun at them, reacts quickly, and they dodge the bullet. Ramirez runs after Julio, but is unable to catch him. After assisting the police investigation, Robert returns to the nightclub and finds Alexandra waiting for him. As dawn breaks, the former lovers stroll through Havana and reminisce. After sharing a kiss, they return to Robert's hotel room and make love. Meanwhile, Juan is busy carousing with Therese.Elsewhere in Havana, Castro's intelligence agent, Nunez (Roger Lloyd Pack), criticizes Julio for attempting an unnecessary assassination on Pulido. The agent tells the brash rebel that if he wants to kill, he should target someone more valuable and shows a photograph of Major Robert Dapes.That morning, Rivero Agüero, a candidate backed by Batista, is announced as the new President of Cuba. At breakfast, Alexandra informs Robert that Agüero was not elected by the Cuban people, but was chosen by Batista in a rigged election. Recognizing that Alexandra is unhappy in her marriage, Robert invites her to leave Cuba with him. However, she reminds Robert that she has responsibilities at the factory and that she enjoys her luxurious lifestyle. As their conversation turns into an argument, she leaves.Meanwhile, rebels call for a nationwide strike on the radio, in protest of the rigged election. At the Pulido cigar factory, Alexandra is unable to prevent workers from leaving as the streets of Havana fill with protesters. Elsewhere, Cuban army soldiers detain Julio, along with other bus passengers, at a military checkpoint. As Ramirez and Robert arrive at the same barrier, Julio withdraws his concealed gun and fires at the soldiers. During his escape, Julio aims at Robert, but he accidentally kills Ramirez instead.Robert then goes to the deserted cigar factory looking for Alexandra and finds Julio with a gun to her head. Threatening to kill Alexandra, Julio orders Robert to drive the three of them to Castro's camp where Julio hopes to prove his worth as a revolutionary by handing over valuable hostages. Along the way, Castro's guerrillas intercept the car. Alexandra and Robert are taken to a gasoline depot that has just been captured by the rebels and are detained with Cuban army soldiers. Unlike the thug Julio, Carrillo (Tony Mathews), one of the rebel leaders, does not want to kill the captives, but instead wants to convert them and win the revolution through strategy. When General Bello and his army counterattack to regain the depot using an armored train, Robert, now fully alienated with the government that hired him, tries to aide the rebels, realizing that the revolution is on the verge of toppling Batista's corrupt government. In a climatic gun battle, Robert commandeers a government tank and opens fire on the government troops. Many government soldiers and rebels are killed or wounded in the battle. Carrillo is wounded in his right leg by shrapnel, but Alexandra manages to tend to his wound. Gutman even joins in on the fighting by manning a heavy .50 caliber machine gun. Gutman shoots up at a twin-engine plane, thinking that it's a government bomber, but it is a charter flight piloted by Donald Skinner, who manages to fly the damaged plane away from Cuba to land safely in Miami, Florida. The end result of the battle is the rebels defeat the Cuban military and capture many government troops, including General Bello.Later on New Years Day, Robert drives Alexandra home and tells Juan that he is taking her away from Cuba now that Fidel Castro will becoming to power. However, Alexandra argues that she feels like a pawn between the two men, and declares that she wants to remain in Cuba, asking Robert to stay with her. Frustrated, Robert leaves to make arrangements for departure, hoping that Alexandra will change her mind and meet him at the airport. As Alexandra drives her sports car to escape, Juan continues to indulge and behave as if nothing will change, but the teenage rebel Julio sneaks onto the property and shoots him dead in the swimming pool.Later, at the airport, Robert, Gutman, and other foreigners, wait in the departure lounge for the last flights out of Cuba and watch as Batista and Don Jose Pulido easily flee the country on private planes. Before boarding, Robert leaves a ticket at the gate for Alexandra. She arrives in time, but instead of joining him, she watches as his plane prepares for departure. Tearful, she returns to Havana alone to face an unknown future without Robert and her late husband Juan. In the city, a large crowd of cheering Cubans welcome Fidel Castro to power.The film closes with the caption 'Cuba, 1959' as the end credits roll over the Cuban flag.