ABSTRACT The recollections of sixteen African American administrators who were some of the first hired in de/segregated school districts in the North are analyzed in order to understand their work lives and experiences in district processes. Findings are analyzed through the lens of workforce diversity perspectives. Five themes emerged from the data regarding race, African American administrators’ roles and experiences. Findings indicate that elements of all three diversity perspectives were present, but the most inclusive, integration-and-learning was least present. Recommendations for further research in contemporary contexts are provided.