Plot

In 1967, Ernesto 'Che' Guevara leads a small partisan army to fight an ill-fated revolutionary guerrilla war in Bolivia, South America.

In 1965, Ernesto 'Che' Guevara resigns from his Cuban government posts to secretly make his latest attempt to spread the revolution in Bolivia. After arriving in La Paz, Bolivia late in 1966, by 1967, Che with several Cuban volunteers, have raised a small guerrilla army to take on the militarist Bolivian movement. However, Che must face grim realities about his few troops and supplies, his failing health, and a local population who largely does not share the idealistic aspirations of a foreign troublemaker. As the US supported Bolivian army prepares to defeat him, Che and his beleaguered force struggle against the increasingly hopeless odds.—Kenneth Chisholm (kchishol@rogers.com)

The film begins in October 1965 with Fidel Castro (Demian Bichir) on local Cuban TV reading a three-page letter from Che Guevara (Benicio Del Toro) which he calls Che Guevara's "Farewell Letter", which Guevara declares his support to Cuba and the revolution, but declaring his intention to leave Cuba to fight for the communist revolutionary cause abroad until the entire world is brought under communist control. Many are left to grasp why Che would leave his family, and the nation that owed him so much, and travel to abroad to start another revolution.

In July 1966, after an unsuccessful attempt to start a revolution in the African nation of The Congo the previous year, Guevara secretly travels to Cuba to visit his wife as well as see his five children (whom are unaware that Guevara is their father). Pretending to be an uncle, Guevara tells his five young children to be great revolutionaries that self-sacrifice is needed to bring change to the world.

On November 3, 1966, Day 1, Guevara arrives in La Paz, the capital city of Bolivia, disguised as a middle-aged representative of the Organization of American States hailing from Uruguay, who subsequently drives into the mountains to meet his men, a small guerrilla army numbering about 50 men, a mix of local Bolivians, Cubans, Peruvians and a few Europeans.

Note: the film is organized by the number of days that Che Guevara was in the country.

On Day 26, there is solidarity among Guevara's men despite his status as a foreigner.

On Day 67, Guevara, however, has been set up for betrayal. He tries to recruit some peasants only to be mistaken for a cocaine smuggler, and the Bolivian Communist Party, led by Mario Monje (Lou Diamond Phillips), refuses to support the armed struggle because they are distrustful of Guevara and his methods of confrontation rather than compromise.

On Day 100, there is a shortage of food and Guevara exercises discipline to resolve conflicts between his Cuban and Bolivian followers.

By Day 113, some of the guerrillas have deserted, and, upon capture, have led the Bolivian Army to the revolutionaries' base camp, which contained vast stockpiles of food, much-needed supplies, and intelligence identifying much of the group as Cubans. Much to Che's disappointment Tamara "Tania" Bunke (Franka Potente), Guevara's East German revolutionary contact has botched elaborate preparations and given away their identity.

On Day 141, the guerrillas capture a small number of Bolivian soldiers that refuse to join the revolution, but soon free them so they can return to their villages. Meanwhile, Bolivian President and dictator René Barrientos (Joaquim de Almeida) calls upon the United States for help to defeat the insurrection happening in Bolivia. A small team of CIA agents and US Army Special Forces advisers arrive in Bolivia to supervise anti-insurgent activity and to train the Bolivian Army.

On Day 169, Guevara's visiting friend, the French intellectual Régis Debray (Marc-Andre Grondin), is captured at Muyupampa by the Bolivian Army along with two of Che's last contacts with the outside world. A Bolivian airstrike then occurs against Che's guerrillas on Day 219, driving them deeper into hiding. By this time, Che has split his forces; his best fighters travel with him in one column, while another column contains other personnel, including Tania, and carries much of the remaining supplies.

Guevara grows sick and by Day 280 can barely breathe as a result of his acute asthma. Nevertheless, he continues to lead his group towards the other column of revolutionaries.

On Day 302, the Bolivian Army wipes out the other column, killing Tania Bunke, Juan Acuña Ñunez, and several others in an ambush as they attempt to cross the Vado Del Yeso river after a local informant tells the Bolivian troops about the movements of the rebels.

On Day 340, Guevara is trapped by the Bolivian Army in the Yuro Ravine near the village of La Higuera. Che is wounded and captured. The next day, a helicopter lands and Cuban American CIA agent Alejandro Ramírez (Yul Vazquez) (a fictionalized version of Félix Rodríguez) emerges to interrogate Che, but without success. The Bolivian high command then phones and orders Guevara's execution (using the code 'Order 600'). He is shot to death by a half-drunk Bolivian army sergeant (Cristhian Esquivel) on October 9, 1967, and his corpse lashed to a helicopter's landing skids and flown out.

In a final flashback scene, Guevara is aboard the Granma back in 1956, looking out over the ocean, as the Cuban Revolution is about to begin. He sees the two Castro brothers alone at the bow of the ship; Fidel is talking and Raúl is taking notes. Guevara hands a peeled orange to one of his comrades and returns his gaze to the lone brothers before the scene fades to black.