Historically and contemporarily the Black male experience has stimulated and provoked meaningful discussions in the realms of sport and academia. Black males are uniquely situated in American society, as they inhabit a liminal existence that oscillates between love and hate. Ladson-Billings (2011) expounds that Black boys are loved in the narrow niches of sport but are often abhorred in academic settings. The majority of research on the athletic and academic identities of Black student-athletes is conducted at the collegiate level in the revenue sports of basketball and football, and the research asserts that the collegiate sport atmosphere renders the two identities as mutually exclusive (Edwards, 1984; Harrison et al., 2011; Singer, 2008). There are studies occurring at the middle school level; however, these studies combine all male athletes into one group and do not distinguish the research participants according to their specific sport participation or racial background (Alfone, 2013; Fuller, Percy, & Bruening, 2013; Gorton, 2010). The few studies that distinguish between race and sport participation are somewhat dated (Mahiri, 1991, 1998; Nasir, 2000, 2008). This study addresses a gap in the literature by focusing solely on elite Black male middle school student-athletes to discover what leads to the seemingly incompatible athletic and academic identities that surface during college. I employed an instrumental case study grounded in Critical Race Theory which investigated and examined the experiences and perspectives of seven elite Black middle school club basketball players. Themes were generated by coding the interview data of all relevant stakeholders such as coaches, players, and parents as well as a thorough analysis of field notes, artifacts, and focus group data. Five themes emerged from the data, Academic Recognition, Athletic Recognition, Career, Racial Expectations, & Time Devoted to Sport and Intellectual Endeavors. This study is significant because it contextualizes the racial, athletic and academic climate of Black male athletes at a crucial time in their identity development. It contributes to the current literature by providing insight and furnishing essential information for parents, coaches and educators in order to bolster and enhance the academic identity and attainment of young Black male basketball players.