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That education globally faces dynamic and polymorphous crises in the twenty-first century is an indisputable fact. How educators build resilience to navigate these crises can gain much from looking at historic challenges educators have faced. This paper draws on and layers important scholarly literature from cultural studies, education history, philosophy, and social foundations to provide contemporary education leaders and policymakers with a method for historicizing the myriad crises they currently must navigate. In addition to broadening educational leadership conceptually to include community collaborators, families, and students, this paper examines three recent historical crises in the context of neoliberalism: language regimes, school closures, and the precarity of teacher labor. Educational leaders’ future crisis-resilience lies in a sound understanding of schooling’s past.