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This paper's main argument is that abolitionist and anti-racist leadership require more than just rhetorical commitments to equity—it calls for a fundamental shift in how leaders are prepared, supported, and evaluated. By synthesizing scholarly literature, program examples, and theoretical frameworks, this study explores the structural and pedagogical features of doctoral leadership programs that explicitly aim to develop anti-racist and abolitionist educational leaders. The paper highlights how programs at institutions like Loyola Marymount University, the University of Connecticut, and others implement these goals through critical inquiry, field-based practice, and community accountability. We identify and present four pillars of transformative preparation as findings. These are, (1) ideological grounding in anti-oppression theory, (2) emotionally reflexive pedagogies rooted in healing and political clarity, (3) cohort-based “counterspaces” that nurture joy, wellness, and solidarity, and (4) inquiry models that center student and community voices in disrupting institutional harm. Importantly, these programs frame leadership not as managerial expertise but as a moral and political project informed by Black feminist thought, culturally sustaining pedagogy, and emancipatory traditions. The leaders trained in abolitionist praxis often face what the paper terms the “triadic squeeze”: emotional exhaustion, institutional resistance, and external sociopolitical hostility. These pressures are exacerbated by rising legislative attacks on anti-racist education, performative equity initiatives, and the weaponization of professionalism to silence racial truth-telling. Without systemic protections, even the most committed leaders face burnout, retaliation, or removal. This synthesis offers three critical implications. First, it challenges leadership preparation programs to deepen their abolitionist commitments by aligning curricula, faculty expertise, and accountability structures. Second, it argues for a redefinition of educational leadership as an affective, relational, and collective endeavor. Finally, it calls for multi-tiered systems of political and institutional support to protect anti-racist leaders from systemic backlash.