The film focuses on a hit man's point person, Jackie Cogan (Pitt), who becomes involved in investigating a heist against the mob.
The film is based on the George V. Higgins novel, which is described as:
Crackling dialogue, mordant humor, and unremitting tension drive the suspenseful stakes of the game higher in Boston's precarious underworld of small-time mobsters, crooked lawyers, and political gofers as George V. Higgins, the writer who boiled crime fiction harder, tracks Jackie Cogan's career in a gangland version of law and order. For Cogan is an enforcer; and when the Mob's rules get broken, he gets hired to ply his trade—murder. In the gritty, tough-talking pages of Higgins's 1974 national best-seller, Cogan is called in when a high-stake card game under the protection of the Mob is heisted. Expertly, with a ruthless businessman's efficiency, a shrewd sense of other people's weaknesses, and a style as cold as his stare, Cogan moves with reliable precision to restore the status quo as ill-conceived capers and double-dealing shenanigans erupt into high-voltage violence.