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This study examines how four African intellectuals—James Emman Kwegyir Aggrey (Ghana), Nnamdi Azikiwe (Nigeria), Kwame Nkrumah (Ghana), and Julius Nyerere (Tanzania)—adapted John Dewey’s progressive educational philosophy to support anti-colonial liberation and postcolonial nation-building. Using historical, comparative, and discourse analysis, the research examines how their reforms integrated experiential learning, civic education, and indigenous values. While their influence shaped early national curricula, the long-term impact varies: Tanzania retains strong ideological continuity, while Nigeria and Ghana reflect mixed outcomes. The study contributes to global intellectual history by highlighting how African leaders reimagined progressive education as a tool for cultural reclamation, democratic participation, and social transformation. Their legacy remains vital in current debates on curriculum reform and educational equity in Africa.