The purpose of this article is to extend the growing counternarrative in education research concerning the negative consequences of school desegregation and its implications for urban education, educational leadership, and policy reform in the post-Civil Rights Era. Guided by qualitative and historical research methods, this article presents the perspectives of eight retired Black school superintendents concerning the goal of integration during the civil rights movement and its disintegration in contemporary urban contexts. Findings reveal that despite desegregation efforts, schools and school systems have never truly integrated and now face a 21st-century brand of educational inequality, what I describe in this article as "vestiges of desegregation," which further undermine the educational opportunities and experiences of those students school desegregation efforts were arguably intended to serve.