As of 2012, data indicate that only one percent of public school teachers are African American males. Numerous reports urge decision makers and higher education professionals to aggressively recruit and retain African American males as teachers in an effort to improve the academic outcomes of African American children in our educational system (Huntspan & Howell, 2012; Lewis & Toldson, 2013). Unfortunately, the voices of male teachers have been under-studied in educational settings, particularly those of African Americans. The purpose of this article is to explore the lived experiences of an African American male kindergarten teacher as to help us understand why African American males rarely choose teaching as a profession. Using a single case study, the researchers and a male African American kindergarten teacher examine these experiences through a racial microaggression taxonomy. Findings revealed that this African American male teacher may be a victim of a cycle of institutional tensions that include microaggressions, as well as an overcomer within the cycle of personal triumphs. Recommendations are provided to improve the experiences of African American male teachers.