In this article, the authors consider both historical and contemporary data regarding the experiences of African American males serving as school principals and employ a framework drawn from the concepts of ethno-humanism and critical race theory. In reporting the findings, we provide descriptions of historical trends and narrative insight into the experiences of four contemporary principals who are African American men. Several common themes were discovered, including a lasting struggle with and against dominant White societal norms and educational policies, a clear focus on and commitment to local community, and an enduring attention to the needs of African American students. The implications of these factors are considered as they contribute to the career advancement or derailing propositions these leaders face.