Background/Context The corpus of scholarship on Black male students who play sports focuses on students at the collegiate level, thus ignoring the regional, neighborhood, and K–12 educational backgrounds and experiences of these young people before some matriculate into a college or university. This omission suggests the need for more robust investigations that (a) focus on Black males during K–12 schooling, (b) place Black male students’ experiences within the larger geographic (e.g., regions, neighborhoods and schools) and social and historical contexts in which they live and go to school, and thereby, (c) seek to understand how these contexts shape students’ experiences and beliefs about race and the role of academics and athletics in their lives and future. Purpose/Objective/Research Question/Focus of Study We investigated two research questions: (1) For Black male students who play high school sports, how do the social contexts shape their experiences and their beliefs about race and the role of academics and athletics in their lives and future? (2) And, what are the consequences of Black male students’ experiences and beliefs for their academic and athletic outcomes? This investigation across geographically and economically contrasting cities, neighborhoods, and schools in the U.S. South (metro Atlanta, Georgia) and Midwest (Chicago, Illinois) offers empirical, theoretical, and practice-related evidence about young Black males’ experiences and beliefs about race, academics, and athletics, while providing a window into the complex social and cultural worlds in which they live, go to school, and play sports. Research Design This article emanates from research studies that employed ethnographic research methods such as interviews and observations, while embedding the researchers within the communities where Black people resided. The research design used a cross-case analysis to investigate participants’ experiences and beliefs. The constant comparative method allowed for the synthesizing of data collected from two different research sites. Description of Main Findings Key findings revealed the importance for researchers to consider place and its implication in the experiences of Black male students who play sports, particularly their perceptions of the role of academics, athletics, and race in their lives. Conclusions/Recommendations This article moves the scholarly understanding of the study of Black male “students who play sports” forward by illuminating the centrality of places, whether a particular country, region, city, neighborhood, or school—in shaping participants’ experiences and beliefs. We offer insights for research, theory, and practice.