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This dissertation is an ethnographic account of educators who occupy the margins of their institutions due to the intersection of non-dominant identities ( Blackness, Latinidad, and/or queerness) and orientations toward liberatory education. It asks how educators who transgress the carceral technologies foundational even to “antiracist” policies move towards freedom in restricted spaces. Using 2+ years of data from charter high schools in Chicago, this dissertation stories political contests that emerge in educators’ relationships with their students, their peers, their institutions, and their contexts, revealing everyday abolitionist steps taken inside the institution. These liberatory educators are prohibited from forging coalitions with each other and with their students, but maintain a steady march toward liberation in ways that contest progressive reform.