In view of global health concerns about elevated levels of inactivity and related disease patterns of citizens, policy reform in physical education and school sport (PESS) is seen as a basic human right and tool for societal transformation. Although literature supports the importance of quality PESS for different aspects of learners’ development, various implementation challenges facing school sports in South Africa have been reported. Drawing on a nationwide research project, this paper seeks to provide empirical insights into the role and status of school sport. Addressing the question, Sport participation in South African schools. Have we lost the plot? This study adopted a blend of self-determination theory (SDT) and social justice theoretical frameworks to understand how educators’ livid experiences impact their personal and social responsibility to teach, enhance, and facilitate PESS to a diverse group of learners in a diversity of schools. Results indicated that school sport is exceptionally varied, multifaceted, and complex, with different pressures and imperatives. It is exacerbated by educators who are required to assume the dual role in schools within a pressurized school environment, which results in overload, emotional rollercoaster rides, and a lack of motivation. Without meaningful motivation, continuous reform, or the revision of policy, the delivery of PESS will remain unachievable.