Given the ubiquity of youth sport, it has the potential to impact character development among millions of American youth. However, findings about the youth sport-character development relation have been mixed. Character education may be necessary to optimize the sport environment to promote character attributes. There is much knowledge of what works in character education within schools, but less is known about character education in interscholastic sports. In this study, we examined athletics directors' (ADs) perspectives of a sport-based character education program from Positive Coaching Alliance (PCA) implemented through their high school athletics departments. ADs discussed factors that mattered for implementing PCA programming, as well as perceived effects of PCA programming among their high school coaches and athletes. Our discussion integrates findings from this study with previous knowledge about effective character education programs in schools. With the goal of using ADs as informants who have expertise in interscholastic sport, findings from this study generated new hypotheses to be tested in future studies to further understanding of character education in sport.