The purpose of this article is to examine how the high school setting assisted the leadership development of African American males. Additionally, we explored how the leadership developed in high school was applied in the post-high school setting. We utilized purposeful sampling to identify and recruit African American male scholar-athletes (N = 27) who were perceived as leaders by their campus constituents at four academically rigorous universities in the western region of the United States. A phenomenological approach was employed to conduct two semi-structured interviews with participants to obtain a deeper understanding of their high school experiences as they related to leadership (as defined by the participants). Data were analyzed to generate textural and structural descriptions about how participants experienced leadership in high school and beyond (Moustakas, 1994). In doing so, three major themes emerged: My Leadership and Involvement Started in High School, My Leadership Has Evolved Since High School, and High School Taught Me to Bond With Others. Findings reveal that the high school setting impacted and informed the future leadership engagement of the participants. Moreover, participants cited an evolution of their leadership post-high school to include involvement in activities that made a positive impact on their respective campuses and local communities. Furthermore, participants noted the influence of group affiliation on their development as leaders. These findings were interpreted within the Social Change Model of Leadership (Higher Research Education Institute, 1996). Practical implications and strategies for high school administrators and educators are discussed.