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Beginning in 1870 as the preparatory high school for African American youth, M Street high school went from an advanced grammar school that employed unqualified teachers and taught under prepared students in overcrowded classrooms to one that has been regarded as one of the premier African American educational institutions in the United States. The purpose of this paper is to explore the educational leadership qualities of Anna J. Cooper of M Street high school between 1902-1930. We are interested in explaining Cooper’s ideologies and strategies that not only educated African American students but also helped to provide a blueprint for leadership. This paper specially focuses on Anna J. Cooper’s radical contributions that sought to elevate the Black race through education.