Background/Context: Historians of education have chronicled the essential link between schools and communities from a variety of perspectives, exploring how ideology, material conditions, and political struggles have shaped public education. Viewing school reform historically allows us to see how schools are tied to their particular contexts, breathing in and out the values, beliefs, and conditions of local communities. This link is especially important to acknowledge in the high-poverty urban communities targeted by school reformers in the current policy landscape, which pits privatization against local democratic control of schools. This paper contributes to scholarship on school reform by portraying a local struggle to reimagine a longstanding neighborhood urban school in the context of an expanding marketplace of school choices. Purpose: Our study uses an asset-based community school development framework to analyze the rich 90-year history of a particular school in the greater Los Angeles area. We were guided by the following research questions: (1) what are the multiple and overlapping demographic, political, educational policy, social, and economic contexts that have shaped or defined the history of the school since its opening; (2) how has this history shaped the community's relationship to the school now; and (3) how does this history inform current efforts to increase public will and community engagement at the school. Research Design: We conducted this historical case study as participants of a local design team comprised of university and school partners charged with re-envisioning a struggling neighborhood middle school as a K-12 university-assisted community school. Data sources included artifacts, primary and secondary historical sources, and in-depth semi-structured interviews with a purposive sample of 14 current and past staff, faculty, alumni, parents, and community members. Findings/Results: Our findings are visualized in a timeline that captures the school's reform history, changing demographics, and community context across three periods of school reform. We interpret this history by focusing on three tensions: reform means versus ends, public versus private goods, and critical hope versus despair. By grappling with these democratic tensions, we conclude, urban communities can counter the dominant policy discourse of failing and turnaround schools to reimagine the promise of neighborhood schools as anchor democratic institutions in urban communities.