Sky Pilot is a story of a community that finds its voice as the racial and social fabric of America post World War II is beginning to change. Post-war Chicago is a place of opportunity for those not afraid to take it. The Pellegrino family has a comfortable business running all the gambling and much of the wholesale distribution on the South Side. However, a new threat has emerged, a gang funded by a mysterious leader takes over the numbers racket. At the moral center of the story is Joe Flint, a lawyer, whose connections, smarts and willingness to dig deep help guide a cast of characters to come to terms with their lives and the changes around them. Follow the business dealings, romantic entanglements and coming and goings of the staff and patients of the Heaven-Up Convalescent Home as the surrounding turmoil deeply affects their lives and how they interact with each other.