In this study the experiences of Black (a.k.a. African Americans/ Negroes) educational leaders were explored focusing on the period during the transition to a more desegregated public- school setting in the state of Florida. Using retrospective storytelling and reflections of 'leading' during desegregation, the lived experiences of those in educational leadership roles were captured in the form of oral histories and analyzed using critical race theory. The effects of desegregation is recounted from their vantage point, from the dissolution of the 'all Black' schools to the impact it had on the communities. The research question was: "What are the stories told by Black people in educational leadership roles about leading during the school desegregation era?" The sub-questions were: "How did school desegregation efforts affect their experiences as Black educational administrators?" "How do counter-narratives about educational leadership manifest in their narratives of leading during the transition from segregated to desegregated schools?" I used tenets of Critical Race Theory (CRT) to interpret the oral history findings and the concept of "structural racism" as a tool to examine the role of race in educational leadership. The findings were that Black administrators told stories and counter stories about racism affecting their employment, they often subverted racialized ranking processes, and they nor their Black communities were complacent in the struggle for racial justice in education. The experiences of these former Black education administrators are discussed as legacy with implications for educational leadership today. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]