In the wake of the federal government's retrenchment from urban America in the 1970s and 1980s and the resulting rise in inequality, youth-serving, out-of-school time (OST) nonprofits took on a greater role in supporting urban public schools and students. Since then, many educational OST nonprofits have become enriching spaces for youth outside of traditional K-12 classrooms. Yet, their reliance on private philanthropic donations to function often complicates their goals. This article uses a critical, participatory, qualitative case study method to describe the experience of a youth-serving community-based education nonprofit organization in a Northeast city in the United States. In order to understand this nonprofit's role in the urban schooling community context, this article analyzes its aims and interrogates its barriers to success, using two theoretical perspectives: social reproduction and community cultural wealth. Qualitative analysis revealed that the organization is unmoored--unable to completely meet its own goals centered on community cultural wealth, because of limiting traditional conceptions of capital that reinforce and maintain unfair racialized power dynamics.