Alan Jensen (Adrian Grenier) is a busy Harvard student with a heavy study schedule, a place on the school basketball team, and a complex romantic life involving two girlfriends, cheerleader Cindy (Sarah Michelle Gellar) and philosophy professor Chesney (Joey Lauren Adams). When his parents' home is destroyed by a tornado, Alan feels the urge to help out, and thinks that the criminal connections of Cindy's mob boss father might be useful. Cindy puts Alan in contact with a crooked bookie who wants him to throw an upcoming basketball game, and the young man does his best. But when it doesn't work out as planned he finds himself performing a delicate balancing act, with the mafia on one side and the FBI on the other.