Examining both the GI Bill and the origins of desegregation of traditionally segregated institutions of higher learning in the South, this historical essay argues that these 2 separate historic markers should not be considered independently. Indeed, to understand the full scope of the GI Bill, we must consider the limited options that Black veterans had when it came to college admissions. Conversely, when considering the desegregation of historically segregated southern colleges and universities, we must also evaluate the strong will many Black veterans expressed in their desire to redeem the federal government's promise for a college education. Building off the body of critical scholarship published on the GI Bill, this article closely examines the enrollment and experience of the first 2 Black veterans to attend the University of Florida (UF), contextualizing the experiences of these veterans with that of other African Americans seeking to gain acceptance to historically segregated public universities in the United States. It also contrasts the African American veteran experience at UF with that of the first White veterans to attend UF following World War II.