Chicago in the 1930s. The United States implemented prohibition and conservative moral values, but this era was a decadent and violent era. The underworld of Chicago was firmly controlled by the Caponi gang. Illinois, where Chicago is located, is a place where Italian and Irish mobs gather. On Rock Island in this state, the Irish-American Rooney (Paul Newman), known as Old Man John, controls the business here. Most of the people living in his community are Irish immigrants and their descendants. Rooney's assistants are his son Kunal (Daniel Craig) and adopted son Michael O'Sullivan (Tom Hanks). O'Sullivan is known as the Angel of Death in the circle and is a formidable professional killer; but he also has his compassion and integrity. More importantly, he values his family very much, is loyal to his wife and two sons, never smokes or drinks, and lives a regular family life. For many years, he has tried to maintain a balance between the roles of killer and husband and father. However, changes suddenly came. Although his two sons, Michael Jr. and Peter, did not know what their father did, they always regarded him as their hero and admired him very much. Little Michael is 12 years old and gradually understands things. He wants to know his father's job. So one day when his father and Kunal are out doing something, he hides in the car. Not long after, little Michael witnesses a murder, and his father is the killer. The gang members are worried that Michael will reveal everything he saw. O'Sullivan only said one sentence: He is my son. However, this does not reassure others. Before little Michael has time to understand the real world and his father, his mother and brother have been killed, and he and his father were the targets of the killing. The father and son began to flee. Although his son begged him not to be violent, O'Sullivan decided to take revenge on Rooney. Rooney and Kunal both hid, and O'Sullivan decided to attack their 3E Cinema business bases one by one until they came out to fight. This plan brought him into conflict with the Caponi faction, because they had business dealings with Rooney, and O'Sullivan's actions harmed their interests. So they sent the killer Maguire to track O'Sullivan and Michael. Maguire (Jude Law) was originally a reporter, and his nickname was "Reporter" after he became a killer. He had only one mission: to kill the father and son. O'Sullivan fled on the road with his son, and the road led to a town called Perdition. Perdition has two meanings: 1) complete destruction; 2) hell.