Watch What's the Worst That Could Happen?

Under the worst possible circumstances, Kevin Caffrey, a professional thief, meets Max Fairbanks, a wealthy businessman who is currently facing bankruptcy. They meet as Kevin is trying to rob Max's home. When the police arrive, Max tells a bald-faced lie, claiming that the ring on Kevin's finger was stolen from Max's house. The police hand the ring over to Max. Thus begins a game of one-upmanship between two professional risk-seekers, neither of whom has much respect for the law. This leaves the women in their lives wondering just how far each of them is willing to go for petty revenge.