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The history of the African American woman in the United States can be described as a struggle for survival and identity within a tripartite of oppression that includes racism, classism, and sexism [Hudson-Weems, C. (1989). The tripartite plight of African American women as reflected in the novels of Hurston and Walker. Journal of Black Studies, 20, 192–207.]. In spite of these challenges, African American women have always considered education an important investment in the future [Gregory, S. T. (1995). Black women in the academy. New York, NY: University Press of American, Inc.)], and despite gender and racial stereotyping that have limited educational opportunities African American females have been inspired to become educators (McFarlin, Crittenden, & Ebbers, 1999). Although African American women are underrepresented in higher educational leadership roles (Ross & Green, 2000; Waring, 2003), little research exploring the development of women leaders in academia, as well of that of existing university presidents, is available (Madsen, 2007). The purpose of this chapter is to explore the career paths of African American university women presidents. This research has important implications to strengthen opportunities to attain these important leadership roles in higher education institutions.