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 puts his creditor against the operator of a gambling ring and leaves his dysfunctional relationship with his wealthy mother (Jessica Lange) in his wake. 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. As his relationship with a student (Brie Larson) deepens, Bennett must take the ultimate risk for a second chance..