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This study explores the history of Harlem Preparatory School, an independent community school in Central Harlem from 1967 to 1974 that successfully educated former “dropout” students and other non-traditional youth. Specifically, this paper highlights the ‘teaching and learning’ that occurred at Harlem Prep, focusing on three elements of teachers’ pedagogy that contributed to student achievement and empowerment: one, the 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 as a pedagogical technique. Ultimately, this historical study—based on extensive archival research and more than two dozen oral history interviews—seeks to use the past to inform, if not inspire, critical educators today.