Jackson Sassaport is a man who often finds himself in the middle. Whether torn between Stella, his beloved and opinionated Yankee wife, and Katherine Marie, the African American girl who first stole his teenage heart; or between standing up for his beliefs and acquiescing to his prominent Jewish family’s imperative to not stand out in the segregated South, Jackson learns to balance the secrets and deceptions of those around him. But one fateful night in 1960 will make the man in the middle reconsider his obligations to propriety and family, and will start a chain of events that will change his life and the lives of those around him forever.