The purpose of this article is to investigate the multiple political histories that have coalesced to produce support for or resistance to the Oakland Unified School District's full-service community schools policy. It analyzes oral history interview data from eight stakeholders who represent the district's major constituencies to explore the reasons why each individual, positioned differently within the larger district system, may or may not support a seemingly democratic, community-based reform. Through their voices, the article explains how different constituencies can interpret an urban district's policies and form community-based coalitions that either further or obstruct a democratic, equity-minded reform.