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Contemporary critical pragmatist theory shapes this project to conceptualize democratic community as a touchstone of ethical educational leadership practice in troubled democratic times. Critical pragmatism understands contingency, community, and hope in the face of struggle, to be foundational to leadership. Contingency names the conditions of pluralism, a feature of democracy, now powerfully polarized. Inclusive community is the means for reconstructing democratic life in our everyday worlds, to build concrete ways to respect and represent student cultures and lives. Hope is the product of shared inquiry and possibility that comes with projects of educational problem-solving, at the school-community scale. Democratic community is understood as a set of commitments, in leadership, to positive freedom, equality, and fraternity in the school organization.