This qualitative study elicited key themes in an attempt to understand the nature and essence of the career advancement experiences of a select group of African American male community college presidents. Research was conducted through a "culturally sensitive" research design (Tillman, 2002) that contained four elements: "culturally congruent research approach"; "culturally specific knowledge"; "culturally sensitive data interpretation"; and "culturally informed theory and practice." A criterion-based sampling was employed to select the five African American male participants to this study (Patton, 1990). These participants were either sitting or recently retired executives with titles consistent with the definition of "president" utilized for this study. Semi-structured interviews were used to gather data and a holistic-content approach to data analysis (Lieblich, Tuval-Mashiach, and Zilber, 1998) was conducted. Research revealed culturally informed career advancement strategies used to by these participants to achieve the position of community college president and suggests strategies for overcoming career advancement obstacles facing future African American male administrators seeking a presidency in American community colleges. The researcher is hopeful that the findings presented here will encourage future researchers to take up scholarly dialogue and/or a discussion of best practices that might serve to address the career advancement challenges facing African American male administrators aspiring for a community college presidency. In particular, comparative research needs to be conducted to provide a more in-depth understanding of how the reported barriers faced by African American males in this study differ from those experienced by their majority counterparts and other underrepresented groups. This research will need to be undertaken soon before a substantial history of lived experiences of African American community college presidents is lost due to pending retirements. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]