Framed by theoretical perspectives on Black Feminist Thought, the life course, and the Generation X/Hip-Hop generation, I present findings from a subset of 10 Black women educators in Birmingham, Alabama who participated in a larger life story project. The participants, who came of age professionally across the pre- and post-civil rights movement (CRM), describe divergent and convergent social and historical contexts that shaped their professionalization, as well as their relationships with and perceptions of Black students and parents. Participants across generation theorize that teaching and leading are activist practices in their own right, which entail clandestine support and silent protest, intergenerational bridge-building, and debunking the myth of Black inferiority. Post-CRM educators, in particular, expressed ambivalence about their urban students' futures. I conclude that multigenerational perspectives should figure more prominently in the scholarship on Black education in the US South. This emphasis could spark new directions and strategies for linking successive generations of Black educators, thereby maximizing opportunities for intergenerational dialogue and collaboration for transformative change in urban education. (Contains 1 table.)