College sport is a uniquely American phenomenon in which participants must split their time, energy, and devotion between two institutions: school and sport. In recent years, the institution faced legal threats and possible player unionization. The research informing these efforts assumes that sports are entertainment based and therefore non-educational (Sperber, 2000; Ingrassia, 2012). Yet framing the conflict for student athletes and schools as education versus entertainment leads to a narrow set of proposed reforms such as paying athletes or eliminating sports (Bowen, 2014; Smith, 2011; Wilbon, 2011). Using participants who are free from commercial pressures—male and female Olympic sport student athletes—this research asks: How do social structures such as race, class, and gender shape student athletes’ ability to negotiate the competing demands of sport and school? To address this question, this year-long qualitative study used multiple sources of data including in-depth interviews and time diaries with student athletes, interviews with academic advisors, and tutors, and various institutional measures. Research and analysis was guided by theories of social reproduction theory and intersectionality. By moving away from an economic-centric analysis of college sport I unveil how the struggles facing student athletes cannot be solved through employee status. Instead it reveals that in the current context of U.S. higher education, school and sport are fundamentally structured to conflict along central areas of college student life: requirements, availability, and legibility. The institutional make-up and legal support of college sport disguises the conflict present and individualizes the resulting educational problems for athletes to navigate on their own. Even athletes with robust economic and social resources struggle to achieve success in both school and sport simultaneously.