The purpose of this study was to investigate the characteristics of African American males and the obstacles they experience on their path to the principalship. A secondary purpose, but very important as well, was to analyze critically the experiences of successful African American male principals to help inform the preparation of principals who lead organizations of diverse demographics. Investigating this area also contributes to the much-needed educational discourse of African American male attitudes, beliefs, and life experiences as principals in education today and how they are meeting the needs of a growing multicultural population. The researcher utilized qualitative methodology in conducting research. The researcher also used a phenomenological research design for this study. Phenomenological research is an empirical inquiry that investigates a contemporary phenomenon within its real-life context using multiple sources of evidence. To select participants, the researcher used a purposive sampling method. The participant sampling was also a sampling of convenience, as the researcher tried to find participants located within the same county of the researcher's residence. The principals were the primary units of analysis, and it was the intent of this study to delve into the lives of the participants to gain a better understanding of the barriers and obstacles they had to overcome to become principals. The findings revealed six common themes that emerged from the data: (a) transformational leadership characteristics, (b) learning for all, (c) minority role models, (d) societal perceptions of African American principals, (e) barriers of African American principals, and (f) principal influence. [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.]