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This qualitative study illuminates the experiences of five adult Black males who attended predominantly white middle-class schools. Recalling their K-12 interactions with school officials and peers, through interviews, they recount overt racism, sexism, and microaggressions. These exchanges prompted conversations around race and racism with their parents and a small number of trusted educators who served as advocates throughout their schooling. This paper details their journeys, analyzes the roles race, racism, gender, and sexuality played in mediating their experiences, discusses intersectionality in relation to their identities and educational attainment, and offers implications and recommendations for educational equity for Black males.