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Drawing on Critical Race Theory (CRT) (Ladson-Billings & Tate, 2016) and Critical Whiteness Studies (CWS) (Nayak, 2007), this study explores the beliefs, ways of knowing and ways of being of 12 anti-racist, mid-level district staff in Ontario, Canada. Findings from participant interviews challenge individual, positive, race-neutral, and de-contextual notions of mid-level leadership. Participants subvert whiteness in the following ways: having a deep understanding identity, structural racism and how power operates within districts; prioritizing collectivization within and beyond the district; and building accountability with leaders that have similar or greater positional power. This study speaks to the importance of identity and context and will be useful for school districts in Ontario and beyond, influencing leadership training, development and accountability.