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This research brings together historical accounts of educational leaders and community organizers who have been targeted by the federal government, yet still developed effective strategies for teaching, learning, and resistance. By surfacing the stories and strategies of Black radicals, transgender rights activists, and Cuban and Indigenous educators, it offers historically informed lessons for justice-oriented educational leadership, even under repressive regimes. Finally, it connects these lessons to an emergent strategy framework that can assist educational leaders in understanding the central and essential role they can play in processes of large-scale resistance and transformative social change.