The Charlestown neighborhood of Boston is renowned for churning out a high number of armed robbers, generation after generation. These robbers never leave their Charlestown life of their own volition, the neighborhood where there is an unwritten code to protect that lifestyle. Such robbers include friends Doug MacRay, James Coughlin, Albert 'Gloansy' Magloan, and Desmond Elden. Doug and James in particular treat each other like family, as the Coughlins have realistically been to Doug since his mother ran off and his father, Stephen MacRay, was sent to prison. Doug has a casual-sex relationship with Krista Coughlin, James' drugged-out single-mother sister. The foursome carry out a mostly-successful bank robbery, but circumstances make them take the bank manager, Claire Keesey, hostage for a short time before releasing her physically unharmed. They find out that Claire lives in Charlestown, so they want to ensure that she saw nothing that could incriminate them if they would ever run into her, so Doug begins a personal relationship with her to find out what she knows and what she's told the police and the FBI, who have taken charge of the investigation. He learns that she has kept some information from the authorities for her own protection--that could specifically identify James. But Doug slowly falls for her, as she does for him. Ultimately, Doug dreams about leaving his Charlestown life to be with Claire--anywhere but there. He must try to keep his true identity from her, and keep the fact that he's seeing her from his colleagues. But leaving is not easy; he and the gang are tasked with a big job by a local gangster named Fergie whether Doug likes it or not. And Adam Frawley, the FBI's lead investigator, comes into evidence that links the foursome to the bank robbery and a subsequent armored car heist, so is on their tail for evidence that will send them away dead or alive.