Given a telephone, small-time scam artist Pendleton Wise, also known as Penny (Vince Vaughn), can talk people into almost anything. But as he whiles away his time in a small office, selling fake travel packages to the unsuspecting public, Penny dreams of something bigger, of the prime gig. His ship finally comes in, in the form of a sexy young woman named Caitlin (Julia Ormond), who spots Penny's talent and invites him to join a project led by the legendary con man Kelly Grant (Ed Harris). Fresh out of prison, Grant is operating in top secrecy. He claims to have found a mine which contains $30 million in gold; if his telemarketers can just raise two and a half million to mine it, the payoff will be huge for everyone.

Penny enthusiastically signs on; he's playing with the big boys now, and as they've promised, the dough is soon rolling in. Within just a couple of weeks, his bank account contains almost a hundred thousand dollars. But trouble ensues after he and Grant become rivals for Caitlin's affections, and Penny loses sight of rule #1: never trust another con. The feature debut of Tony-award winning theater director Gregory Mosher, the film is a moody and sensitively acted thriller.