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This chapter focuses on two aspects of the achievement gap – underachievement and low achievement among Black males in urban school contexts. More specifically, the authors explain several problems/issues confronting Black male students in P-12 gifted and talented, advanced placement, and special education programs, along with the school-to-prison pipeline – inequitable discipline in the form of suspensions and expulsions. We parse underrepresentation and overrepresentation for this student group. A central part of this discussion is grounded in the achievement gap literature on Black students in general with implications for Black males in particular. Another fundamental aspect of this discussion is the need for educators to adopt an anti-racist (social justice or civil rights) and cultural competence approach to their work, which means being equity-based and culturally responsive in philosophy and action. Suggestions for closing the achievement gap and otherwise improving the achievement of Black males are provided for educators. We also compel educators to go beyond talking about equity by setting quantifiable equity goals for minimum and maximum percentages (and numbers).