Beach bum and petty criminal Jack Ryan (Owen Wilson) gets into a fight while working at a construction site owned by corrupt developer Ray Ritchie (Gary Sinise). The cops want him out of Hawaii, but shifty judge Walter Crewes (Morgan Freeman) intervenes and hires Jack to work odd jobs at a string of beach bungalows. Jack then encounters Nancy Hayes (Sara Foster), Ritchie's beautiful but dangerous mistress, who draws him into a plot to rob Ritchie of a fortune.