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This paper explores the philosophies of progressive education in the United States in the 1970s through an examination of the rise of alternative and community schools in Milwaukee, Wisconsin. Ideas conventionally associated with progressive education including child centeredness, schools as spaces of self- discovery and the concept of freedom are explored along with the new roles of teachers and students. The narrative is based on existing documents, as well as retrospective interviews of founders, teachers, former students. The study examines a range of initiatives and debates through the cases of two independent community alternative schools. The stories of the teachers and founders reveal the divergent implementation of progressive philosophies and showcase the interconnections between people and institutions.