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This study examines Chicago Public Schools’ Whole School Safety (WSS) initiative as a case of participatory policymaking in urban education. Prompted by community advocacy and racial justice movements, WSS explicitly sought to replace centralized safety mandates with localized, community-driven planning processes. Drawing on interviews with district officials and community-based organization leaders, the study analyzes how WSS embodied core principles of empowered participatory governance while revealing persistent institutional constraints. Findings highlight three interrelated themes: building deliberative infrastructure, restorative governance and healing-centered labor, and navigating structural fragility. The study extends governance theory by emphasizing affective and relational dimensions of policymaking in racially stratified systems and contributes to equity-centered policy research by documenting lessons for designing durable, community-engaged education reforms.