In this article, we explore community schools, as first theorized through community organizing, in relation to movements for racial justice in education to address the following question: How has educational equity been radically imagined by the community school movement in New York City to reframe how we understand success, meaningful school experiences, and the possibility for hope, healing, and racial equity in education? Using ethnographic methods, we answer this question by examining what went into the grassroots commitments of organizers and the grasstops implementation of the community schools' strategy at the district level. This examination sets a context for exploring what we saw happening at the school level, where we observed community meetings with organizers and district officials and interviewed key stakeholders about their deep histories of advocating for equitable reform. Drawing on an abolitionist paradigm, we describe how organizers such as those in NYC, who were interested in transforming systems as a prerequisite to advancing freedom, were the first major advocates of the original community schools project. Valuing the knowledge and strength of communities that have survived and thrived in the face of centuries of oppression, we conclude that community stakeholders in collaboration with education workers, from organizers to students, envisioned a blurring of communities and schools as part of a strategy to build collective power that both exposes and challenges injustice.