Doug MacRay is a longtime thief, who, smarter than the rest of his crew, is looking for his chance to exit the game. When a bank job leads to the group kidnapping an attractive branch manager, he takes on the role of monitoring her – but their burgeoning relationship threatens to unveil the identities of Doug and his crew to the FBI Agent who is on their case.

The true story of Whitey Bulger, the brother of a state senator and the most infamous violent criminal in the history of South Boston, who became an FBI informant to take down a Mafia family invading his turf.