In a study of the New Orleans public schools, African American males represented 43% of the school population, while accounting for 58% of the non-promotions, 65% of the suspensions, 80% of the expulsions, 43% of the dropouts, and only 9% of the gifted and talented. African American males are denied equal educational opportunity at such alarming rates that some writers have dubbed them an endangered species. The societal ramifications of this systemic non-education have lead to a proliferation of research studies addressing the tragedy of being young, Black, and male in America. The current study attempts to engage with this issue by first stepping away from the framework within which teachers, politicians, and academics have situated the problem - that of society's expectation of the five D's: "dumb, deviant, disturbed, disadvantaged, and dysfunctional" (Cooper & Jordan, p.383) and seeks instead to understand and probe the (counter)identities African American males assign themselves when not being forced to answer the question, "How does it feel to be a problem?" (Du Bois, 1903). This study seeks to understand the mechanisms by which African American male adolescents situate themselves within or without the paradigm of deviance and the implications this holds for successful academic interventions.