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This study describes the reality of educational leadership as understood and experienced by Black male school principals and heads of school within a context of navigating racialized spaces, the politics of race, and racism in schools (Echols, 2006; Horsford, 2014; Lomotey, 1989, 1993). The qualitative study used survey, phenomenological, and visual elicitation methods to examine the lived experiences and perspectives of 14 Black male school leaders in the U.S. Data were analyzed within a critical race theory (CRT) methodological and interpretive framework utilizing narrative, biographies, storytelling and counter-storytelling, culturally responsive proverbs, scriptural passages, and aphorisms. In navigating racialized spaces as a Black man in the principal’s office, the leaders found that they were constantly viewed through a prism where their Blackness and Black racial identity were constantly under inspection, suspicion, discrimination, and direct assault and racism through the normalized power relations of Whiteness. 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. These leaders developed a range of strategies that enabled them to navigate the multidimensional aspects of their racial identity within a dominant White-racialized education system. The research expands understanding of paradigms of critical race leadership and disrupts the normative educational leadership that ill-serve significant sections of our student populations and communities. The research builds theory and formulates a new and comprehensive definition and typology of Black male school leadership.