Mike, having taken a part time job to make ends meet driving a delivery truck for a fellow rounder, Knish, (John Turturro) who also witnessed his loss to Teddy KGB, stops off on his way home to deliver papers to his law professor, Petrovsky (Martin Landau), who is playing poker with colleagues and several judges. Stunned by the loss he decides to concentrate on his law school studies, and makes a promise to his girlfriend and fellow law student Jo (Gretchen Mol), to not play cards anymore.
Young hotshot poker player Mike McDermott (Matt Damon) loses his entire bankroll of $30,000 in a hand of Texas hold'em against Teddy 'KGB' (John Malkovich), a Russian Mobster, who runs an illegal underground poker room Mike frequents.