Mike McDermott (Matt Damon) attends law school and lives with Jo (Gretchen Mol), a classmate. She's trying to keep him on the straight and narrow far away from what she perceives as his gambling addiction. He's done well over the years in New York's underworld of back room poker games. But after he loses a big wad of money to Teddy KGB (John Malkovich) in a high stakes game, he has to take a job making truck deliveries for Joey Knish (John Turturro), his gambling mentor, just to pay his bills.
Despite his good intentions to study, he is drawn back into the poker world when Worm (Edward Norton), his best friend and card-playing buddy, is released from prison. A vicious debt collector (Michael Rispoli) wants $15,000 from the ex-con, and Mike finds himself caught in the middle. His law school dean (Martin Landau) helps him see that you've got to follow your bliss no matter what happens.
In his bestselling The Soul's Code, James Hillman writes: "A calling may be postponed, avoided, intermittently missed. It may also possess you completely. Whatever, eventually it will out. It makes its claim." This gritty and engaging film directed by John Dahl provides a fascinating meditation upon this process. Through several critical choices and a few frightening darkenings, Mike eventually finds his way to his true calling as a world class poker player.