The goal of this study was to provide a qualitative look at the factors associated with the academic engagement and success of Black male student-athletes in high school. The research team employed a thematic analysis to examine semi-structured interviews conducted with two successful Black male student-athletes, along with their principal, teachers, parents, and coaches. The results suggest that a consistent, collaborative approach laden with cultural competence is necessary to facilitate such outcomes. The study is viewed through the lens of Bronfenbrenner's ecological systems theory, and implications for the results are discussed for several education stakeholders. Suggestions for future research and practice are provided.