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This study explores the history of Harlem Preparatory School, an independent community school in Central Harlem from 1967 to 1974 that successfully educated former “dropout” students and other non-traditional students. Specifically, this paper highlights the unique community coalition that Harlem Prep administrators and supporters cultivated, bringing together a very diverse range of supporters across racial and ideological lines including Black activists, local Black-owned businesses in Harlem, major philanthropies, and giant (white-owned) corporations. Contextualized within recent history of urban education scholarship on the antagonistic relationship between schools and communities in cities, this paper offers an alternative story about how a school successfully partnered with its community in ways that can inform educators and activists today.