The purpose of this study is to document the segregated schooling reflections of Black school superintendents and explore how those experiences informed their educational philosophies in the post-desegregation era. Critical race theory is used as a methodological and analytical framework to present participants' reflections of living in segregated communities, going to all Black schools, working to meet the high expectations of parents and teachers, and how those realities shaped their self-concept as Negro students. Study findings support the growing body of literature on valued segregated schools and negative consequences of desegregation on the education of Black students, but its significance lies in the uniquely informed perspectives of the Black school superintendent. It concludes with a discussion of implications for the future of Black education. (Contains 1 table.)