Jim Bennett (Mark Wahlberg) is a risk taker. Both an English professor and a high-stakes gambler, Bennett bets it all when he borrows from a gangster (Michael Kenneth Williams) and offers his own life as collateral. Always one step ahead, Bennett pits his creditor against the operator of a gambling ring (Alvin Ing). He plays both sides, immersing himself in an illicit, underground world while garnering the attention of Frank (John Goodman), a loan shark with a paternal interest in Bennett’s future.