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This study uses critical content analysis to examine novellas written by children’s author Mildred Taylor. The novellas are first situated within a tradition of historical fiction for youth written by African Americans. We offer an analysis undergirded by Critical Race Theory and Afro-Pessimism as interpretive tools for explicating the ways Taylor depicts white supremacy throughout the stories. Three themes emerged: 1) ‘boundaries and place’: inscribing white dominance, 2) antiblackness – undermining the struggle for selfhood, and 3) acts of subjugation and brutality. These novellas provide openings for discourse in classrooms around the racialized experiences of Black people in the South, giving young readers windows into the historical underpinnings of white supremacy and the structures leading to its rootedness in contemporary society.