Drawing on experiential, literary and historical narratives, this article connects the long history shaping the school-to-prison-pipeline to the contemporary experiences of Black youth in today's educational system. It maps abolitionism from its origins as a movement to end slavery through the ongoing Black freedom struggles that have challenged state and vigilante violence throughout the eras of Jim Crow and Civil Rights to today's efforts to dismantle the prison state. By situating the criminalization of African American education from our nation's founding until the present with particular focus on the post Brown years, the article stresses how policies that funded policing over education persisted through liberal and conservative administrations. This longer and broader historical approach to school discipline should help teachers, school administrators and policy makers devise anti-racist teaching practices that can resist the seemingly unyielding and ever adaptable strictures of white supremacy, most recently evidenced in the attacks on "Critical Race Theory," "Diversity Equity and Inclusion" initiatives and so-called "wokism." By listening to how those who have been enslaved and incarcerated regarded education, I join a chorus of voices suggesting how we might structure our pedagogical choices as a fugitive practice that looks for solutions outside the institution and imagines as yet unthought of alternatives to the ways punishment is incorporated into today's public education.