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This participatory research illuminates critical educational leadership that strives to center all children and communities in resistance to unjust educational systems built upon centuries of racial capitalism. During individual storytelling interviews and collaborative inquiry group experiences on Zoom, leaders reflexively express their desires to create and sustain anti-racist, economic-justice-focused and community-centering spaces of learning while navigating dilemmas they’ve experienced during global pandemic and Black Lives Matter uprisings. This project lifts up progressive justice-centering school leaders who reclaim and reimagine education for liberation, equity, healing and care in ways that are critically conscious and responsive. Leadership that honors the coexistence of desire and dilemma, contestation and community helps us make sense of how we can change the structures of schooling itself.