In Sing With Me, Carlisle Jacobson begins a teaching career in Washington, D.C., learning as much as he is teaching. Through personal experiences, he learns most youths don’t have the advantages he enjoyed in the horse country of northern Virginia only a day-trip away from Washington but worlds away from its streets plagued by crime and nearly cut off from hope as a child of privilege and wealth, with slave owners of the antebellum south in his ancestry. A hunting enthusiast since he was young, Carlisle still is alarmed to learn firearms are used frequently in D.C. for hunting down other people, including one of his student's and a co-worker. His most frequent teacher in learning he has a lot to learn is Lucia Sanspeur, a black woman with ancestry that extends to Colonial era settlers on the Delaware River, including a man who performed a heroic mission during the Revolutionary War despite the white militia leaders disdain for his skills and initiative. Lucia’s voice captivates Carlisle from their first encounter and her ideas propel him toward understanding that he looks at the world and other people through a sense of white wealth and privilege. When he experiences first-hand the violence and crime that victimize many in the area daily, Carlisle’s education moves into advanced studies but also comes to nearly a complete stop.
