While there is an abundance of interdisciplinary research on boyhood, education, and sport respectively, especially as relating to males of color in the United States, the extant education scholarship has a dearth of auto-ethnographic work that examines these areas. Hence, this article examines how sport, and specifically, basketball, links to the development of masculinities, identity, and critical pedagogies within our own “education.” Further, considering the various tensions around the schooling of U.S. youth from minoritized backgrounds, we leverage our backgrounds as Chicanx and African American scholars to recollect and analyze our journeys and links to our boyhoods and sense-making in formal and informal spaces of play. Our findings entail a push for a re-examination of how sports and critical identities of race and class may work in dialectical and transformative ways, even amidst various contradictions of boyhood. Rather than perpetuating a view of basketball cultures as solely reproducers of harmful masculinities, this paper imagines the pedagogical and liberatory aspects of the game. We conclude with implications for research around gender identities within formal and informal play.