Michael Sullivan Sr. (Tom Hanks) is a trusted aide to John Rooney (Newman), an Irish American organized crime boss. Sullivan, an orphan and a soldier in the Great War, was adopted by the older man as a child, and he has been working with him ever since his teens. Rooney treats Sullivan as a surrogate son, being closer to him than his own son and heir, the vain and insecure Connor Rooney (Daniel Craig). Further frustrating Connor, his father treats Sullivan's two sons, Peter and Michael Jr. like grandchildren. At a wake of a former buisness associate, Michael Jr. and Peter notice the subtle friction between their father and Connor.
Sullivan senior and Connor are instructed by Rooney to deal with Finn McGovern, another employee of Rooney's whose brother was murdered by the Rooney organization as punishment for allegedly stealing from them. Unbeknownst to both Michael Sullivan and Connor Rooney, a curious twelve-year-old Michael Sullivan Jr. hides in the car and witnesses the ensuing scene where Connor, acting against his father's wishes, murders McGovern. The shocked Sullivan Sr. swears his son to secrecy, while John Rooney humiliates his son by demanding an apology for his seemingly hotheaded actions. Ostensibly to prevent the threat of Sullivan Jr. divulging the murder he witnessed (but in reality feeling jealous of and threatened by Sullivan Sr.), Connor, again against his father's wishes, attempts to have Sullivan murdered at the same time as personally killing his wife Annie and younger son Peter. Both Sullivan Sr. and Jr. survive the attempt on their lives and flee to
When it becomes clear that Al Capone's crime syndicate will not countenance Sullivan's goal of taking revenge on the Rooneys, he develops an elaborate scheme to protect his son and to blackmail the mob into giving up Connor by robbing its secret accounts in banks throughout
It later becomes apparent that Connor has been embezzling money from his father, holding the money under the names of gang members that he has murdered. Confronted by Sullivan with the evidence that his son has been betraying him, John Rooney refuses to stop protecting Connor. He reminds Sullivan that, they too, are murderers, that this life they chose, and that "none of us will see heaven." Wanting his son to avoid traveling the road he has taken in life, Sullivan has a difficult decision to make. In order to gain revenge and protect his son, Sullivan must then kill the members of Rooney's gang, including John Rooney. He is then able to track down and avenge himself on Connor. Since Capone protected Connor because he was only Rooney's son, there was no more reason to hide him after his father was dead.
Subsequently, the psychopathic (and disfigured) Maguire succeeds in tracking down the Sullivans and murders Michael Sullivan senior at a beachside house in Perdition. Apparently, he traced a call placed from Sullivan to his wife's sister, Sarah, and he was able to determine that they were headed for the town of
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