In the climax of “The Town,” Doug and his crew plan one last heist, targeting Fenway Park during a Boston Red Sox game. However, the heist goes awry when they are confronted by the FBI. During the ensuing shootout, Jem is killed, and Doug is wounded but manages to escape.
Doug realizes that he needs to leave town to avoid capture by the FBI. He meets with Claire one last time to say goodbye and reveals his true identity as one of the bank robbers who kidnapped her. Despite this revelation, Claire agrees to keep his secret and wishes him luck in his escape.
As Doug prepares to leave Charlestown for good, he decides to confront the local crime boss, Fergus “Fergie” Colm (played by Pete Postlethwaite), who has been pressuring him to stay in the criminal world. Doug kills Fergie and his bodyguard, tying up loose ends before leaving town.
In the final scenes, Doug boards a freighter and sets sail, leaving Charlestown and his criminal past behind him. Meanwhile, Claire visits the FBI and provides them with a false description of Doug, allowing him to escape detection.
The film ends with Doug looking out at the ocean, contemplating his future and the possibility of starting a new life away from the crime and violence of Charlestown.
Overall, the ending of “The Town” provides closure for Doug’s character arc, as he makes the difficult decision to leave behind his old life and pursue a fresh start. Despite the loss of his friend Jem and the challenges he faces, Doug ultimately finds redemption and hope for the future.