This dissertation fills a gap in the historiography of southern higher education by focusing on five university presidents and their role in the desegregation of a non-elite flagship university in the Upper South. While historian Melissa Keane has studied the presidential role at elite private southern universities during the initial phase of the desegregation process, no study has yet examined desegregation from the president’s office at a southern land-grant university. Building upon historian Peter Wallenstein’s thesis that desegregation is not a single event in an institution’s history but rather an ongoing process, I argue that it was also process that clearly involved the university presidents. Though much has been written about desegregation in Kentucky generally and the University of Kentucky specifically, and the pioneering African American students who desegregated UK, almost no scholarship has focused on the specific role of the UK presidents in the ongoing desegregation process. In much of the existing literature, the presidents are portrayed as spectators, they occupy a backseat, or they sit on the sidelines as the action unfolds. Often their story ends with the initial desegregation of UK’s graduate and undergraduate programs. Passive observers they were not, however. Herman Lee Donovan, Frank Graves Dickey, John Wieland. Oswald, Albert Dennis Kirwan, and Otis Arnold Singletary implemented policies that impacted the course of desegregation at the University of Kentucky.