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Youth-serving out-of-school time (OST) non-profits are uniquely positioned 501(c)(3) organizations between the public sector and the private sector, which has historically made them difficult to study (Halpern, 2003). This critical qualitative dissertation study embraces OST non-profit’s complexity to illuminate how one organization operates in the liminal and contradictory space between urban public schools, city students, and the private funders that keep them afloat. This study asks the overarching research questions: How does a youth-serving OST non-profit navigate between an idealized set of social justice values and a system of capitalism? In what ways does racial capitalism impact the work of this organization? And how does this organization navigate this impact?