Sydney (Philip Baker Hall – Psycho) is a poker-faced professional gambler with a soft heart for a hard luck story. He plays guardian angel to unlucky John (John C. Reilly – The Thin Red Line) and a hooker, Clementine (Gwyneth Paltrow – Shakespeare In Love), whom he grows to love like family. When John's and Clementine's honeymoon night leads to a disastrous hostage situation, Sydney takes care of it, as usual. But when slick casino pro Jimmy (Samuel L. Jackson – Star Wars: The Phantom Menace) threatens to reveal a secret from Sydney's past that could destroy his relationship with the newlyweds, Sydney decides to hedge his bets and not leave anything to chance.