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The purpose of the paper was to understand the multiple biases and injustices encountered by successful Black female superintendents, and how they utilize strategies and relationships to ensure success, with a focus on large urban public-school districts. A phenomenological research approach was used, building upon two key theoretical constructs, feminist standpoint and intersectionality. Three findings will be discussed:(a) racism was an explicit issue while establishing equitable procedures and structures; (b) these superintendents were frequently faced with "glass-cliff" circumstances and double standards for performance; and (c) sexual and racial discrimination was sharply encountered outside the district, in the community. New and aspiring Black superintendents must be better prepared by certification programs to face the realities of these positions.