Since the creation of American higher education, the majority of the nation's colleges have been led, managed, and directed by White men. From the Boards of Trustees to the dean level, racial representation in higher education leadership has traditionally not included people of color. This lack of diversity in senior leadership is juxtaposed against recent increased efforts at faculty and student diversity, particularly within Predominantly White Institutions (PWIs). A critical examination of the career trajectory of Black male presidents of PWIs was administered through a phenomenological research design in order to gain a better understanding of what it takes for Black men to obtain and maintain these positions. Results from the study show that although the Black men interviewed do not have identical career paths, there are some shared experiences. Professional leadership development, careers spent predominantly in PWIs, and mentors are all factors that significantly affected the career trajectory of these men on their way to the presidency. Data from this study is instructive for institutions and organizations dedicated to the academic and professional achievement of Black men. [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.]