Sport has the potential to serve as a context in which youth can develop as players and people. Positive youth development (PYD) through sport is a prevalent strength-based approach that aims to promote life skills acquisition in youth participants. The purpose of this article is to demonstrate the utility of critically interrogating PYD through sport using critical race theory (CRT). Select key tenets of CRT serve as analytical tools that can highlight potentially problematic assumptions that underline current approaches to PYD through sport. Interrogation of PYD through sport using CRT exposes its limitations in theory, research, and practice. This race-centered perspective can help to "reimagine" sport coaching for positive development from a more socially responsible, critical praxis.