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Black British Feminism (Mirza, 2009) and Black Feminist Thought (Collins, 2000) are used as theoretical frameworks to analyze the lived experiences and leadership practices of three Black women “firsts”-- Yvonne Conolly (London, 1969), Betty Campbell (Cardiff, 1973), and Gertrude Paul (Leeds, 1976) —who were head teachers and members of the Windrush generation, the first significant wave of African Caribbean immigrants to Britain. A variety of archival sources as well as oral history accounts were used to create biographical portraits that explore their self defined leadership stance and “everyday acts of resistance” in their schools and wider communities as “outsiders within” an often hostile British educational environment.