The purpose of this chapter is to investigate the characteristics of African American school principals and the obstacles they experience on their path to the principalship. A secondary purpose, but very important as well, is 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 principal attitudes, beliefs, and life experiences of principals in education today, and how they are meeting the needs of a growing multicultural population. The principals are the primary units of analysis, and it is the intent of this chapter to delve into the lives of the participants to gain a better understanding of the barriers and obstacles they have to overcome to become principals.