Jim Bennett is a risk taker. Both an English professor and a high-stakes gambler, Bennett bets it all when he borrows from a gangster and offers his own life as collateral. Always one step ahead, Bennett pits his creditor against the operator of a gambling ring and leaves his dysfunctional relationship with his wealthy mother in his wake. He plays both sides, immersing himself in an illicit, underground world while garnering the attention of Frank, a loan shark with a paternal interest in Bennett's future. As his relationship with a student deepens, Bennett must take the ultimate risk for a second chance.