Mike Sullivan works as a hit man for crime boss John Rooney. Sullivan views Rooney as a father figure. However after his son is witness to a killing he has done Mike Sullivan finds him self on the run trying to save the life of his son and at the same time looking for revenge on those who wronged him. Jude Law co stars as a hit man hired to kill Sullivan.
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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.
