Two separate school districts--a city one and a county one--operated independently in Durham, North Carolina, until the early 1990s. The two districts merged relatively late compared to other North Carolina cities, such as Raleigh and Charlotte. In Durham, residents in both the county and city systems vehemently opposed the merger until the county commissioners ultimately bypassed a popular vote. African American advocates in the city school district, in particular, faced an impossible trade-off: city schools increasingly struggled financially because of an inequitable funding structure, but a merger would significantly threaten fair racial representation on the consolidated school board. This article explores this core tension in historical context by looking at several failed merger attempts from 1958 to 1988, as well as the 1991 merger implementation, against the backdrop of desegregation, economic transition, profound metropolitan changes, and protracted political battles in Durham.