Doug MacRay (Ben Affleck) was born and raised in Charlestown, a blue-collar neighborhood in Boston, where crime is a part of life. Charlestown is the world's capital for carjacking, kidnappings, and armed robberies. The tricks of the criminal trade are passed down from father to son. Doug is the brains and ruthless leader of a gang of bank robbers who have been able to get out clean after each bank robbery. But Doug knows that his luck will not last forever, and he is looking for one last big heist that will give him the chance to leave the town in his rear-view mirror. But no one will let him, especially, his right-hand man "Jem" James Coughlin (Jeremy Renner); because he believes that it would be a personal betrayal to him, and he is not going to allow that. In a recent bank job, Doug forced the bank manager Claire (Rebecca Hall) to open the safe, and then took her hostage as leverage for the getaway, and eventually setting her free unharmed. Doug knows that he should leave Claire alone, but she only lives four blocks from him, and he can handle it, but he begins to fall for her. Their romantic involvement is about to take them down a perilous path.