Educational research that effectively addresses larger sociopolitical and sociohistorical contexts must interrogate macro-level decision-making and policies "and" prioritize the lived experiences of those who directly affect and are affected by social structures. This project explores racial and economic justice work in schools by centering the perspectives of those progressive educational leaders who strive, work and grapple to center "all" adults and children within our larger unjust education systems. As individual leaders share their stories through one-on-one recollections and in critical collaborative inquiry groups, they illuminate spaces of contestation, continuity and liberation. The context of both continuous and unfolding pandemics along with heightened resistance to racist structures, policies and practices that occurred during 2020-2021 shape the study's contours. These leaders share their individual and collective reflections about their own stances towards liberatory education by telling dilemma stories about their daily on-the-ground work and how they navigated the social, economic and political context of the global COVID pandemic and Black Lives Matter uprisings in the U.S. By holding voices of leaders of color and voices of white leaders alongside one another, we begin to see how their affective experiences of leadership are often starkly different. These leaders' dilemmas and desires illustrate the radical possibility of creating and sustaining humanizing, liberatory and community-centered spaces of learning. Engaging theories and methods of critical bifocality, transformative activist stance, critical affect theory, descriptive inquiry and critical whiteness studies, this critical qualitative project considers deeply philosophical and political questions about the present and future of progressive education. The study poses questions about progressive school leadership that reclaims and reimagines schooling for liberation, justice, equity, healing and care in ways that are always collective and critically reflective, purposeful and responsive to the children, families, and communities we work with, leadership that perhaps might even change the structures of schooling itself. This project's provocations include 1) shifting towards a praxis of collectivity in research and school leadership, and 2) contesting the ways differently racialized and gendered leaders are constrained and empowered within systems of education built upon centuries of patriarchy and white supremacy. Listening to and co-conspiring with justice-centering progressive leaders allows us to enact and expand what progressive schooling is and can be, for all children and adults. We who believe in freedom cannot rest. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]