Black male teachers tend to enact culturally relevant pedagogical practices that support the academic achievement, cultural competence, and critical consciousness of Black male students. Using critical race theory, culturally relevant pedagogy, and life history methodology, we explore the life history and work of a Black male middle school teacher to examine ways in which his historical, societal, institutional, and communal and personal experiences have shaped him to become a culturally relevant teacher and advocate for Black male students. In doing so, we provide implications and recommendations for preservice teacher education programs to retain and better support Black male middle school teachers.