Johnny Sharansky is a forty-three-year-old gambler who has avoided gainful employment for twenty-three years. He takes big risks, crazy risks sometimes, but none bigger or crazier than his pursuit of a young, high-class shiksa, Margaret, who is fascinated by organized crime figures. His infatuation lands him in deep trouble with the law, the blue-blood's fiancé, and the Chicago mob.

Johnny is savvy and slick, but he still has a big lesson to learn, and his North Shore obsession is ready to teach the well-heeled gambler A Dandy Little Game.

Set in Chicago in 1944, McCulloch's novel evokes a period of post-Capone operators, petty racketeers and high society ingenues waiting out World War II.