This article examines the educational leadership of the first African American female principal in Richmond, Virginia: Mrs. Ethel Thompson Overby. It seeks to ascertain, through a historical framework utilizing critical race theory, how this particular educational and instructional leader conceptualized academic achievement given the context of segregation, known for its lack of resources, physical inadequacies of facilities, underfunded schools, underpaid teachers, and limited social, political, and economic power of students and their communities. More important, this research assesses what measures Overby as a school leader developed to foster the academic achievement and excellence of urban African American youth at the Elba School. We argue that this research documents how one African American female principal and her teachers conceptualized achievement beyond test scores to include other measures of achievement, such as educational access, critical and cultural literacy, community engagement and empowerment, citizenship education, and equal opportunity and success of the whole individual beyond standardized tests scores such as reading. It is hoped that today's educational leaders can learn from Overby's fostering of purposeful outcomes intended to thwart the institutional structures of racism while empowering the individual and community to view achievement as equal access and opportunity. (Contains 2 tables.)