Deep down, Pendleton 'Penny' Wise (Vince Vaughn) is a good man, but you wouldn't believe it if his job is anything to go by. Everyday, he convinces unwary sun worshippers to part with their hard earned cash for dodgy package holidays until the operation closes down and he winds up in financial dire straits. Tired of working on small time deals, Penny yearns for that deal that will bring in the mega bucks. It arrives when he gets headhunted by Caitlin Carson (Julia Ormond) to work on an operation led by telesales guru Kelly Grant (Ed Harris) who has just left prison.

Despite doubts about Grant's legitimacy, Penny signs up for the prime gig. Working in top secrecy, the headhunted team of top talent sets about selling shares in $30 million goldmine in Arizona for big, big rewards. Soon Penny is out pacing his fellow sales people and getting bonuses from his boss, of which Carson (Grant's mistress) is one. But things start to go wrong, when Penny's conscience kicks in and he realizes he has ignored golden rule number one - never trust another conman.