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This study examines the relationship between superintendents’ leadership during COVID-19 crisis and the political contexts in which they lead. Three large urban district cases were chosen: New England, Midwest, and South. Extant conceptual literature on crisis, organizational crisis, and complexity theory are used to make sense of the differential experiences between communities and leadership across three urban districts in distinct political contexts. Broad brush findings include: 1) Local crisis experiences as fractals of political context, 2) decision optimization in terms of stakeholders’ relative power; and 3) leveraging crisis for social justice.