Surfer dude and occasional thief Jack Ryan (Owen Wilson) takes a baseball bat to the head of the menacing Lou Harris (Vinnie Jones), a foreman on a Hawaii construction site run by corrupt millionaire Ray Ritchie (Gary Sinise). The police and Ritchie's right-hand man, Bob Rogers Jr. (Charlie Sheen), all tell Jack they want him off the island as soon as he's out of jail. A local judge, Walter Crewes (Morgan Freeman), has different ideas. He seems to take a liking to Jack and offers him a job as a handyman at a small resort of beachfront bungalows he owns. Ritchie has been cheating on his wife with a much younger mistress, the sexy Nancy Hayes (Sara Foster), who catches Jack's eye. The judge warns him that she likes "the criminal type" and can't be trusted. Together they break into houses for fun and profit, then come up with a scheme to steal $200,000 from Ritchie. Harris and Rogers both come looking to get even with Jack. And it turns out that Nancy is not the only one he can't trust.