This study investigated the risk and protective factors of 11 high-achieving African American males attending 4 urban charter high schools in a Midwestern city to determine what factors account for their resilience and success in mathematics courses, and in high school more generally. This research was guided by a Phenomenological Variant of Ecological Systems Theory, which assisted in extrapolating how these young Black males make sense of their experiences despite the many challenges they face growing up in urban Black America. Results indicate that although students were under multiple forms of academic and physical threat within and beyond school walls, there was a keen presence of academic agency and an ability to manage potentially threatening situations to cleverly protect themselves from complex systems of risk.