For the last decade, research has shown concern about the pool of African American candidates for the superintendency. Nationally, African American candidates make up two percent of superintendents and fourteen percent of the teaching force, the pool from which superintendents are traditionally chosen. Increasing demands to meet the needs of culturally diverse students is a reality of the 21st century school administrator. As a result, the underrepresentation of African Americans in administrative leadership is problematic. This dissertation describes the experiences of five African American superintendents specific to career paths and navigation of the job search process. It identifies the factors that help or hinder African American superintendents in maintaining their positions. Additionally, it explores Du Bois's concept of double consciousness through participant counter-stories. A critical race theory framework was used to explore the relationship among race, racism, and power in the narratives of African American superintendents. Through stories that challenge the mainstream, discrepancies between the cover and the reality of authentic experience were exposed. Utilizing grounded inquiry, theories were derived from interview data acquired over a one year period and through analysis of resumes. Data were analyzed by first identifying categories and concepts and continuing to refine and categorize as new data were collected. Larger themes were then tested to develop emergent theories. Finally, emergent theories were validated with superintendents. Study findings underscored differential experiences between the male and female superintendents. When analyzing the career paths of the participants, the two male African American superintendents had career paths that mirrored those of the typical white male superintendent. In contrast, the paths of the women were generally not as direct. Significant differences were also noted in the nature of the first superintendency. Even when utilizing strong mentor networks, females were selected by districts in significant turmoil. Additionally, differential experiences were seen as females chose to serve in their positions for a longer period of time. The study concluded by suggesting that future studies delve further into the nature of the experience of the African American female superintendent. Implications for recruitment and retention were discussed and recommendations for practice were suggested. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]