Bud Collins can't win at anything. His daughter calls him a loser, his ex is taking him to the cleaners, and he can't beat his bookie. Getting lucky with women is also a lost cause until a strange package arrives in the mail and offers him the opportunity of a lifetime. His eccentric uncle wants him to come to take care of his house while he takes a long vacation with his future in-laws in Australia. The incentives are lots of money and a mystery hinting his cash-poor uncle, who is always trying to figure out a gambling angle to break the bank, is onto something big.

Bud finagles a phony medical leave from his job and heads to Reno, Nevada, where he is stunned to discover his uncle, who has already left on his trip, wants him to take care of an incredible mansion instead of the decrepit home he remembers from his youth.

Bud learns more about his uncle's money-making scheme when he starts substitute teaching at a job his uncle has arranged for him through a friend. He also meets a woman who might be the girl of his dreams. But he accidentally blows his chance with her and thinks he will never see her again until learning she works at his school. However, Mary Jane isn't interested in a jerk, and Bud, with his students' hilarious help, has to start winning her heart all over again.

Eventually, Bud realizes how his uncle has been making tons of money, and he can't resist taking advantage of that knowledge. However, when he starts making some cash, he sets in motion a wild course of events destined to change his life—for as his fortunes turn, it causes repercussions which get his bookie, Vinny the Shark, and his devious hit man, Slinky, on his tail, along with a few other shady characters determined to stop him from succeeding in becoming rich and possibly winning the love of his life. They all want their cuts, and they all have their scams to dump Bud right back where he started.

Bud soon has to decide what he wants the most: money, love, or his simple, safe life back. It seems he can't have everything—or can he? Will his preposterous idea to outwit everyone work? Maybe or maybe not...because his eccentric uncle still has a loaded ace up his sleeve which no one, including Bud, sees coming, and that card just might trump everything!