This qualitative study takes account of the salience of activism in informing the worldviews and professional practices of a multigenerational sample of 42 African American educators in Birmingham, Alabama. Framed by life course, Black feminist thought, and hip-hop educational research perspectives, the study highlights how the participants grapple with: generational misunderstandings; re-visioning traditional notions of activism; and forging intergenerational alliances. Birmingham, forever bound by its haunted yet sacred civil rights history, is presented as a prototypical space for examining this inquiry and sparking a resurgent activism among African American educators. The author concludes with implications for the capacity of contemporary African American educators in the U.S. South to forge intergenerational alliances to advance the aims of African American education.