In 1933, Ethel Thompson Overby became the first African American female principal in Richmond, Virginia. Her motto was "It is better to light a candle than to curse the darkness" (Overby 1975, 1). Before becoming principal, Overby had been a teacher in the southern urban "de jure" segregated schools of the city. How did the racially segregated context impact her understanding of democracy as an African American woman? As a teacher, what educational practices did she subscribe to? What educational theorizing underpinned her educational practices as a teacher and as a principal? Who was she? These were the questions that guided this research into the educational theorizing of Ethel T. Overby. This research seeks to further the understanding of the theorizing that underpinned the educational practices of African American female teachers and principals who taught and led in public urban "de jure" segregated southern schools (Charron 2009; Johnson 2000; May 2007; Walker 2009). This historical qualitative research provides knowledge about the educational theorizing of African American educators and how past practices can support the educational fortitude of African American students today. (Contains 5 notes.)