Jack Ryan (Owen Wilson
) is a likeable drifter whose talents lie just outside the law. Hoping a change of scenery will bring him luck, Jack heads for Hawaii. There on the exotic North Shore of Oahu, he soon discovers that whether he is looking for a new con or a little romance, temptation is everywhere. Jack takes a job working construction for Ray Ritchie (Gary Sinise
), a shady real estate developer who is building a resort despite protests by local Hawaiians. Almost immediately, Jack has a run-in with Ray Ritchie's foreman, Lou Harris (Vinnie Jones
), and cold-cocks him across the jaw with a Louisville Slugger. Bob Jr. (Charlie Sheen
), Ritchie's right-hand man, warns Jack to get off the island if he knows what's good for him.
Jack happily ignores Bob Jr. Impressed with Jack's knockout ability, North Shore District Judge Walter Crewes (Morgan Freeman) offers Jack a job while taking an unusually keen interest in Jack's past crimes and uncertain future. Enter Nancy Hayes (Sara Foster), a thrill-loving local who specializes in good looks and petty crime. When Nancy tries to seduce Jack into helping her double-cross Ray Ritchie and steal $200,000 of his payoff money, Jack is intrigued, but hesitant. This could be the perfect score, or the perfect setup.