There is an underrepresentation of African American males in K-20 education. The problem is that resiliency could be a factor that contributes to the underrepresentation of African American male leaders. Research suggests that American students could obtain their high school diploma without learning from an African American male instructor. Yet, studies show that children benefit from the instructional practices of a teacher of color, especially Black students. The purpose of this qualitative study was to explore the resiliency of African American male leaders in Northeast Florida to understand factors related to their underrepresentation at all levels of K-20 education. One of the gaps in the literature indicated that studies are needed to demonstrate how the underrepresentation of African American leaders could impact student achievement. Through the lens of transformational and resilience theoretical frameworks, the research questions focused on factors that impact African American male leaders' underrepresentation and ways to minimize African American males' representation gap in K-20 education. Qualitative methodology was an appropriate fit for this study. Through the ethnographic design, the sixteen participants shared lived experiences. Snowball sampling was used to select from a population of African American male leaders with a minimum of five years of teaching experience, African American males, and held a leadership position. Semi-structured one-on-one interviews and a focus group were used for data collection, and thematic analysis was used to interpret the data. Internal and external circumstances and appropriate support systems emerged as key results. The conclusions suggest that recommendations should formalize collegial networks and prioritize forming professional and personal relationships. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]