Recruiting and retaining African American students is an ongoing challenge for many post-secondary institutions. This dissertation examined the contributing factors to this increasing dilemma and review strategies that may be helpful in the retention of African American male college students. This study also examined the instructional leadership style and forms of integrative measures used to help first, second, and third generation African American male college students to acclimate to academic environments that serve to prepare and potentially nurture them for professional and personal growth. African American male college students who attempt to engage in educational endeavors in post-secondary education was the emphasis of this study. Data collection involved the interview of 11 participants. Content analysis was used to review elements that may be similar or different for African American male college students. The results of the analysis produced six thematic categories relevant to the experiences of the participants. These thematic categories were (a) influence, (b) support, (c) challenges, (d) generational differences, (e) social atmosphere, and (f) significance. Several recommendations were made based on the results of the study. These recommendations centered on empowering African American males to pursue education and to have a positive outlook in coping with life challenges.