The negative consequences of school desegregation on Black families, educators, and communities in the US are well documented in education research today. The purpose of this article is to examine the experiential knowledge and wisdom of practice of former Black school superintendents who attended all Black segregated schools and led desegregated school districts. Using critical race theory as a methodological and analytical framework, I seek to advance our understanding of how the positive aspects of valued segregated schools can improve Black education today. Findings include Black superintendent reflections of and calls to action concerning separate and unequal schooling contexts according to the following constituencies: the Black community, the Black parent, the Black teacher, and the Black student. Building on the participant directives for political engagement and community-based activism, I conclude with a discussion about transforming Black education through a political race project aimed to resist educational inequities, advance racial justice, and promote social change in education.