Synopsis for
Road to Perdition (2002) More at IMDbPro »

Michael Sullivan, Sr. is an enforcer to John Rooney, an Irish American organized crime boss in Illinois during the Great Depression. Sullivan, an orphan raised by Rooney, has worked for the crime boss most of his life. Sullivan and Rooney's son, Connor, are sent by Rooney to talk to Finn McGovern, a disgruntled employee. Sullivan's son, twelve-year-old Michael Sullivan, Jr., follows the enforcers, witnesses Connor's impulsive killing of McGovern, and stumbles into discovery by Connor and his father. Although Sullivan swears his son to secrecy, Connor tries to seal the secret with a failed attempt to kill Sullivan, while murdering Sullivan's wife, Annie, and the younger son, Peter. Sullivan and his son Michael escape the attack and flee to Chicago.

Sullivan requests assistance from Al Capone's crime syndicate to seek revenge, but when he is rejected, Sullivan and his son plan a string of robberies to steal the syndicate's laundered money. Sullivan hopes to coerce Capone into giving up Connor for the money, but Capone instead dispatches assassin Harlen Maguire to kill Sullivan and his son. Maguire sets up a trap for Sullivan with the aid of Rooney's accountant, Alexander Rance. Sullivan arrives at Rance's hotel room, seeking assistance, and Rance stalls him long enough for Maguire to appear. Rance is killed in the crossfire of the ensuing gunfight, but Sullivan escapes, however he is shot in the arm. Maguire receives a superficial wound to his face, where debris is embedded down one side of his head, but he survives. Sullivan's son takes his father to a farm where a childless and elderly couple helps the former enforcer recover. During his recuperation, Sullivan finds in ledgers taken from Rance that Connor had embezzled money from his father under the names of gang members that he had murdered.

When Sullivan recovers, he secretly meets with John Rooney during Mass and shares his discovery about Connor. Rooney refuses to let his son be harmed. Sullivan is forced to hunt down and kill members of Rooney's gang, including John Rooney himself. With the crime boss dead, Capone finds no reason to protect Connor anymore, and Capone's lieutenant Frank Nitti gives Sullivan a tip to track Connor down and kill him. Apparently free from pursuit, Sullivan and his son make their way to the town of Perdition, Michigan. A disfigured Maguire surprises Michael Sullivan Sr. in the summer house of Sarah (Annie's sister). Maguire shoots Sullivan Sr. from behind, and the assassin finds himself held at gunpoint by Sullivan's son. Maguire approaches the son as Sullivan discourages his son from firing to have blood on his hands. Sullivan is able to shoot Maguire from behind instead, and Sullivan dies in his son's arms. The son mourns his father's death and finds his way to the elderly couple that had helped him and his father, growing up with them.