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Urban school districts are zones of contestation where hegemonic (dominant) ideas are reified, redefined, and resisted around the control of public schools and beyond. Since the early 1980s, the pressure to improve achievement and tackling deep inequities faced by low-income students and students of color has reshuffled the policy actors and organizations leading efforts to improve schools through curricular, organizational, and financial reforms. Community engagement amid educational crisis and privatization exists within a limited set of policy options influenced by elite actors and constrained by political-economic conditions, but less is known about alternative ideas and strategies obscured in the process of coalition-building. This paper is a comparative case study of school district politics in Oakland and Berkeley, California that explores how local stakeholders navigate new partnerships through sustained coalitions called “urban regimes,” or “education regimes” in this context, to shape education governance in a portfolio district versus a traditional district. Drawing on interview, participant observation, and financial data, along with urban regime analysis, I outline how regimes attempt to maintain power and respond to pushback through “regime evolution” and “regime cooptation,” two underexplored areas in the literature. Preliminary findings indicate that education regimes are critical in bridging dominant ideas with local pressures to create the semblance of authenticity for philanthropic projects, revealing key contradictions and fissures within hegemonic notions of district privatization.