Jack Ryan (OWEN WILSON) is a small-time criminal whose bad luck and bad choices have led him to Hawaii in search of greener pastures. Yet, it's not long before he gets into trouble again at a construction site where he works for shady real estate developer Ray Ritchie (GARY SINISE). As the locals protest the razing of land, Jack cracks Ray's foreman, Lou Harris (VINNIE JONES), on the head with a baseball bat.
Jack is eventually let out of jail and is hired by District Judge Walter Crewes (MORGAN FREEMAN) who has him work as a handyman at the coastal motel he runs, but oddly seems just as interested in Jack's criminal background.
Another person seemingly interested in him is Nancy Hayes (SARA FOSTER), a young woman who's having an affair with Ray. While he's away with his wife, Alison (BEBE NEUWIRTH), Nancy wants Jack to help her rob him of the $200,000 he reportedly has lying around his hunting lodge. Their sudden and close time spent together doesn't sit well with Bob Rogers, Jr. (CHARLIE SHEEN), Ray's married right-hand man who's smitten with Nancy and has been ordered to get Jack off the island.
Falling deeper for Nancy, Jack starts to scope out and plan the robbery, all while dealing with the notion that there may be more to her, the crime and the rest of the players than it initially appears.