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This study describes the experiences of Black male school leaders from across the Northeast region of the USA in navigating racialized spaces, including the politics of race, and experienced racism in educational settings as well as in school leadership. Data analysis utilized a CRT and culturally sensitive methodological and interpretive framework. Participants generally found themselves marginalized, even ostracized from the dominant organizational power bases and decision-making structures, on the basis of their race-culture identity, Blackness, and leadership identity as Black male principals and heads of school. Results suggest a developmental model and demonstrable pathway for Black leaders to successfully navigate the pitfalls of the white gaze and experienced negative professional and personal reactions to “leading while Black and male”.