This study utilizes ethnographic methods, in-depth interviews, and observations to investigate the neighborhood and high school experiences of Terry, an academically and athletically high-achiever. Originating from a multiple case study methodology that examined the experiences, perceptions, and aspirations of Black male students who played high school sports, this research draws from examinations that investigated the experiences of Black males in their neighborhood, school, and athletic settings. The findings highlight how Terry escaped from "bondage" by displaying characteristics of resourcefulness. Although he experienced violence in his neighborhood, the combination of support from family members, exposure to an advanced academic curriculum, and sports participation at an early age protected Terry from becoming a victim or a participant in violent crimes. Furthermore, Terry received an athletic scholarship to attend college but aspired to use his athletic skills as a platform to earn a business degree and a PhD. This study has implications for expanding the understanding of the perceptions and aspirations of Black male students who play sports in urban neighborhoods and at urban schools. Furthermore, it provides policymakers and administrators insights that can further develop programming and activities that support the social and academic advancement of Black male students who play sports.