This article examined academically and athletically motivated Black male students who play high school sports. In-depth interviews and observations illuminated their experiences, beliefs, and aspirations in their Chicago neighborhood and school context. The notion of Place and Critical Race Theory framed their experiences. Yosso's communities of cultural wealth were utilized to analyze their experiences. Family members were instrumental in guiding these adolescents as they participated in recreational activities, enrolled in advanced classes, and participated in sports. This study concludes with implications for education, policy, society, and educational outcomes for Black male students, and Black male students who play sports.