When a routine money drop goes awry, Big Jim Cartoni decides to do the unthinkable: get out of the mob. Acting on his dream of opening his own club and going legit, he's foiled at every turn by lifelong nemesis, Joey Moran, all the while hoping his boss doesn't find out about the club until it's a success. With the city of Chicago as its' backdrop, follow the story of one man who tries to beat the odds without ever having to fix the numbers.

Bill Dancer and his young companion Curly Sue are the classic homeless folks with hearts of gold. Their scams are aimed not at turning a profit, but at getting enough to eat. When they scam the rich and beautiful Grey Ellison into believing she backed her Mercedes into Bill, they're only hoping for a free meal. But Grey is touched, and over the objections of her snotty fiancé.