The story is based on events in the life of Pino Lella from June 1943 to May 1945. In Milan, 17-year-old Pino Lella knows that the Nazis are struggling to keep their hold on Italy, but all the teenager dreams about is getting a date. He approaches a young woman and asks her to meet him at the cinema later. She agrees and tells him her name is Anna.
Pino and his younger brother, Mimo, sneak out of their house to go to the movie. Anna never shows up, but the boys enjoy the film until Allied planes bomb the city. Pino and Mimo escape and make it home. Mimo is sent to Father Re, a priest who runs a school for boys in the mountains. Pino and his family evade the nightly air raids by taking the train out to the country and sleeping in fields. After their apartment and purse store are destroyed, Pino is also sent to Father Re.
When Pino arrives at the train station, Alberto Ascari, a boy about Pino’s age, meets him. Alberto aspires to be a racecar driver and demonstrates his skill as he weaves through mountain roads. Pino promises to teach Alberto how to ski if he will teach Pino how to drive.
Father Re welcomes Pino to the school. The following day, Father Re wakes him before dawn and makes him hike in the mountains. Each day, the priest assigns Pino a new trail and longer miles to trek. After a week, Pino is allowed to take the weekend off. He visits Alberto, and true to his word, his friend teaches him how to drive.
When Pino returns to the school, Father Re continues to make him hike. Pino soon learns why. Father Re eventually asks Pino to guide three people, who are Jews, over the mountains to Switzerland. Pino safely escorts the two men and one woman over the difficult mountain pass to safety.
Over the following weeks, Pino continues to lead Jewish refugees and escaped Allied pilots to freedom in Switzerland. He teaches Mimo and several other boys the different routes through the mountains so they can also help. On New Year’s Eve, Pino celebrates with his friend Alberto.
Partisans break into the party and demand the guests give them money to help them fight the Germans. Their leader, Tito, warns Pino to keep off certain passes or he will turn him over to the Nazis. But, as the winter progresses, Pino continues to use all the passes through the mountains in order to save the Jews. The partisans attempt to kill him, but he survives.
Pino has many close calls with avalanches, Nazis and the partisans before he is ordered by his father to return to Milan on a matter of life and death.
Back home, Pino is told he must register for the army because he will be 18 in a few weeks. If he waits, the draft office will put him into the fascist army and send him to fight in Russia. He would have a 50/50 chance of surviving. Pino’s father wants him to register with the German army in the OT, or “Organization Todt.” They do not fight on the Russian front. Pino reluctantly agrees in order to keep suspicion from his family, after a family friend is arrested for espionage.
Pino becomes a soldier. His hand is wounded when the train station he is guarding is bombed. He is sent home to Milan to recuperate. One afternoon he sees a Nazi soldier trying to fix an officer’s car. Pino offers to help, using the knowledge he gained from his friendship with Alberto.
He impresses the officer, Gen. Leyers, when he is able to get the car started. Leyers makes Pino his new driver. That night, Pino’s Uncle Albert explains that Leyers is the most powerful German in Italy. He has intimate knowledge of Hitler and the German war effort.
He asks Pino to spy on Leyers for the resistance, and Pino agrees. The hardest part of the assignment is that he must not tell the truth about his activities to anyone else. The rest of his family and his friends believe he is willingly serving the Nazi officer.
Pino is shocked to see Anna when he goes to pick up Leyers the following morning. She was the young woman who stood him up the first night Milan was bombed. She works as a maid for Leyers’ mistress, Dolly. Pino is thrilled to be back in contact with Anna as he has often thought about her in his dreams.
As he chauffeurs Leyers, he comes in contact with the “gray men.” These are prisoners, Jews and Allies, dressed in gray and used as slave laborers for the Nazi army. Pino is appalled at the men’s appearance and furious at Leyers for his obvious abuse of the prisoners.
Leyers has Pino serve as a translator between him and Benito Mussolini. Leyers needs Mussolini to end the machinists’ strikes in Milan and Turin. Mussolini agrees, but demands that Leyers arrange a phone call with Field Marshal Kesselring and Adolph Hitler. Leyers promises to try.
As Pino drives the general, he picks up as much information as he can about troops and armaments to pass on to the resistance. He is desperate to get into the general’s locked valise to see the top-secret papers inside. One night when the general leaves the valise in his mistress’s apartment, Pino seizes the opportunity. He finds the general’s spare key in Dolly’s jewelry case but is discovered by Anna.
Thinking he is a thief, she threatens to tell Dolly, until Pino convinces her he is a spy. He makes a wax impression of the key so he can get a duplicate made. Instead of opening the valise that night, Pino and Anna celebrate their small victory by having a romantic interlude in Dolly’s kitchen.
When he returns home that night, he discovers Mimo hiding. Mimo has left Father Re to join the resistance. He is appalled to see Pino in a Nazi uniform. For his own safety, Pino cannot tell Mimo the truth about his spying on the general. Mimo leaves in the morning, convinced that Pino is willingly serving the Germans.
Pino witnesses numerous Nazi atrocities: the brutal shooting of partisan prisoners; the beating and starvation of slave laborers; the looting of towns and farms for food; and soldiers beating and shooting anyone who tries to stand in their way. Pino also sees Leyers supervising a secret transfer of gold bars onto a rail car. Pino races back to the general’s car in order to remain undetected. He hears four gunshots. One for each prisoner that helped the general loads the gold.
As winter approaches, the situation in Italy becomes more desperate. Leyers forces factories across Italy to provide his soldiers with supplies. Cases of wine and cows are stolen to give the soldiers a merry Christmas, while Italians are left to freeze and starve. But there is some good news. Pino and Anna’s love for each other continues to grow. The two are inseparable, whenever they get time away from their jobs.
In a rare act of compassion, Leyers saves several Jewish children from being sent to a concentration camp. Instead, he has Pino take them to the Cardinal of Milan for safety. Leyers does several favors for Italian factory owners, promising to keep their factories from being destroyed when the Allies defeat Germany. Pino knows it is the way the general has gained success. He does favors for people so that when he needs help he will have people who owe him.
In April of 1945 the war is coming to an end. Mimo returns to Milan. He knows Pino has been spying for the resistance and the two brothers reconcile. Mimo gives him orders from the resistance to arrest Leyers in two days. Pino spends a wonderful night with Anna before she and Dolly plan to leave Milan for the safety of Innsbruck.
Two days later, Pino acts as a translator between Leyers and an American officer. The general promises to order his men not to fight when the Allies enter Milan. As Pino translates, he tells the American that the Nazis are burning all their top-secret documents.
Pino arrests the general that evening and delivers him to the resistance. As Pino walks back to the city, gunfire and grenades break up the celebrations about the war’s end. Nazis, partisans and fascists all fight for control of Italy. In the morning, Pino walks through streets littered with bodies. He meets with another American officer who asks for his help getting into the telephone exchange and also arranging for alcohol, women and music to be brought in for a party that night.
Pino is successful in his task, even playing piano in a band with his friends for the dance. The night is a blur of alcohol and joy. Bleary-eyed, Pino walks home in the morning, still in his uniform. He is mistaken for a fascist and chased through the streets with gunfire. Desperate to escape, he runs to Dolly’s apartment. He had expected to find it empty, but he discovers it has been trashed. Dolly and Anna were taken prisoner before they could escape to Innsbruck.
Pino finds himself drawn to a square in the town. Nazi collaborators are being led out for execution. Among them are Dolly and Anna. Too scared to try and save her, Pino watches in horror as the mob shoots the woman he loves. The following day, the American officer takes him to see the execution of Mussolini and his mistress. Pino is appalled at the mob’s insatiable thirst for revenge.
Pino is asked to help the Americans one more time. He and his friend are to transport an American ally to safety. Pino agrees, only to discover it is Gen. Leyers he must save. Pino evades Allied tanks and partisan gunfire, but then points his gun at Leyers as the general leaves the car to urinate. Pino accuses him of caring for no one but himself.
When Leyers argues that he cares for Pino and Dolly and Anna, Pino tells him of the women’s deaths. Leyers then delivers the devastating blow. If Pino had not arrested him, the general would have made sure they had been evacuated. Pino is the reason Anna died.
Despondent, Pino allows Leyers to live. Although he prays for death as he continues to drive through the war torn mountain pass, he delivers the general to safety. Before they part, Leyers shakes Pino’s hand and calls him by his codename in the resistance. Stunned, Pino is left to try and understand who Leyers really is and what part he played in the war.
In the aftermath, we learn that although Pino survived the war and became a successful businessman, he never truly recovered from all he had seen and the loss of his true love. He married and divorced twice, had four children and lived the life of a jetsetter. Leyers survived an allied POW camp and went on to live on an estate in Germany.