This article, based on archival research and oral interviews, examines the personal and professional impact of desegregation on African American teachers in an urban southern setting by focusing on the life stories of two public school teachers, Kathleen Crosby and Bertha Maxwell-Roddey. Both taught in segregated schools, helped to desegregate Charlotte's public schools, and later forged successful career paths as administrators from 1946 to 1986. Focusing on the motivating factors and educational theories of these exemplary womanist teachers offers a window into the lives of educators who forged new avenues for advancement in the urban South. This article also analyzes how the professional careers of Crosby and Maxwell-Roddey are emblematic of Tamera Beabuboeuf-Lafontant's theoretical concepts of womanist teaching. Patricia Hill Collins also argues that womanists strive to ensure group survival while pushing for institutional social change. Desegregation-era teachers such as Crosby and Maxwell-Roddey exemplify this dual purpose by expanding their mandate to serve to encompass political action as they challenged discriminatory school administrators and parents. These teachers practiced a form of caring activism that not only encouraged gender equality, but also adopted concepts of cultural nationalism to help Black children develop a positive self-identity (Beauboeuf-Lafonfant 2005, Collins 2000).