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Since its founding in the nineteenth century, Philadelphia’s public school system discriminated against Black students and teachers. As the city’s Black population increased in the twentieth century, segregation and overcrowding worsened. During the 1960s, numerous attempts were made to reform schools through progressive education—e.g., child-centered learning, independent study, and community input into curriculum and governance. This historical paper will use interviews, archival documents and literature to explore two West Philadelphia schools founded on such concepts, University City High School and the West Philadelphia Free School. It will ask whether the progressive features of these schools, and the circumstances of their founding, helped or hindered the cause of educational equity.