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At the intersection of history, race, politics, and urban school reform, this commentary will consider Karen Lewis’s life and leadership in the context of other Black women education leaders historically. From the 1960s through the 21st century, multiple waves of reform significantly restructured urban education—from the War on Poverty and Civil Rights-era struggles to No Child Left Behind and policies informed by Project 2025. Centering Black women’s stories across these significant historical transformations, uniquely reveals the immense challenges facing urban districts and communities, as well as new theories, practices, and organizing strategies to confront these challenges. In addition to serving as an important political text, Karen Lewis’s memoir is a significant addition to the archive of Black women educators’ history. With many Black women educators lacking personal archival repositories for their papers, memoir and autobiography constitute important sources to preserve the historical past, reveal the histories of marginalized communities, and generate new research.