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If teachers want to build authentic relationships with Black male students, they must make space in their classrooms for honest critical conversations about race and racism that acknowledge their students’ realities and honor their identities. In this paper, I examine how one White male teacher and one Black male teacher at a racially diverse Catholic high school created classroom environments where their Black male students felt comfortable engaging in meaningful conversations about race. I explore how the teachers’ identities, particularly their racial identities, influenced the way they approached conversations about race, the race-based topics they addressed, and the purpose the conversations served for their Black male students.