The social movement for #PoliceFreeSchools (and the adjacent campaign on college and university campuses called #PoliceFreeCampuses) welcomes an opportunity to reimagine school discipline and safety in contradistinction to current carceral forms. Scholars have moved away from notions of "school to prison pipeline" by demonstrating the many ways schools are organized as carceral spaces (e.g., school-prison nexus). A conceptual framework of "Anti-carceral leadership" is put forward in this paper to underscore the need for a leadership paradigm that actively refuses the logics of the carceral state (e.g., social control). The paper underscores how the logics of antiblackness may sustain mechanisms of social control in education policy intended to undo racialized harm. The tensions of be(com)ing an anti-carceral leader and its significance for undoing technologies of punishment, confinement, and constraint that reinforce schooling as a site of Black pain and suffering are discussed.