Today, more than half a century after Brown v. Board of Education, many institutions of higher education, particularly predominantly white institutions (PWIs) are still grappling with issues related to increasing diversity. And while many Institutions of higher education (IHE) now boast large numbers of students from diverse backgrounds, the same cannot be said of the diversity of upper level administrators particularly within PWIs. However, what research has shown is that most IHEs desire and value diversity. However, the means of achieving diversity are many, varied and contested. This study attempted to add to the body of existing literature on diversity within PWIs by drawing upon narratives of Black and White upper level administrators on issues of hiring and career mobility. By contrasting the careers of Black and White upper level administrators within one PWI in the southern United States, this study explored through their narratives what those narratives tell us about the impact of race on the processes of recruiting, hiring, promoting, and retaining upper level administrators within the PWI. NVIVO 7 was used to code and organize the interviews. The interpretation of the findings was framed and viewed through the lens of Critical Race Theory (CRT). Specifically, CRT was used to understand ways in which the political category of race impacts the hiring and career mobility of Black upper level administrators compared to their White counterparts within the PWI. The ideas of CRT were used not only in interpreting the findings of this study, but in framing it as well. More specifically, this study examined the effects of race and explored how race is deployed and experienced at the individual, institutional and to some extent, societal levels as evidenced in the narratives of the participants in this study.