Clinton, Mississippi. 1943. World War II. Jesse, a young black boy, just received his first shoe shine box. Excited to grow up and become a "working man," he begins shining shoes in front of Mr. Carl's restaurant. However, Jesse soon learns that working in the Jim Crow South is more complicated than he thought. When he is asked to give a free shine to one of the prisoners from Camp Clinton, Jesse discovers that the enemy is not necessarily who he thinks it is.