Within urban elementary schools are Black students who continue to challenge the normative deficit characterization of the educational opportunities of students like them. This study attempts to provide a more holistic picture of the scholarly trajectories of 13 African American males who are particularly talented in mathematics and who attended urban schools. PVEST to used to explore stage-specific outcomes to identify dynamic and situational risk and protective factors, both internal and external, by which these young men operate and negotiate within multiple contexts to achieve success in and beyond their classrooms. Results identify major traits that foster mathematics identity development and academic achievement.