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This study explores the history of Harlem Prep, an independent community school in Central Harlem from 1967 to 1974 that successfully educated former “pushout” and other non-traditional students. Specifically, this paper explores Harlem Prep’s ‘teaching and learning’, focusing on three elements of teachers’ pedagogy that contributed to achievement and empowerment: one, breaking down of the traditional teacher-student hierarchy; two, employing culturally relevant teaching (in the complicated context of the era); and three, the tangible use of love. Ultimately, this historical study—based on extensive archival research and more than two dozen oral histories—seeks to historicize and compare Harlem Prep’s pedagogical strategies to other Black schools of this era with the purpose of better understanding the diversity of emancipatory teaching.