Purpose: This article considers the perspectives of superintendents who attended all-Black segregated schools and examines how their lived experiences informed their views on desegregation policy, programs, and practices. Research Design: This empirical, qualitative study used critical race theory as a methodological and analytical framework for collecting and interpreting participant narratives acquired through in-depth, semistructured interviews and autobiographical and biographical documents and artifacts. Findings: Study findings are presented as counterstories to (a) the inferior all-Black school, (b) equal education, access, and opportunity, and (c) integration, diversity, and inclusion, with implications for the perceived viability of school desegregation in the post-"Brown" era. Collectively, they reflect what one participant described as "mixed feelings" about school desegregation. Conclusions: The article concludes with implications for educational policy and practice to include support for racial literacy in educational leadership and policy and recommendations for promoting a proper education no matter the school context, separate or mixed. (Contains 9 notes and 2 tables.)