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History is centrally involved in place development. Given the historical importance of antebellum slavery, it is little surprise that it profoundly shaped the social and economic future of the United States. What is perhaps more surprising is the link to local, county-level development as it relates to contemporary systems of black disadvantage. Through our focus on one aspect of school segregation in the American South, namely racial disparities in public school enrollment, we contribute to the literature on the legacy of slavery by examining how this local link persists. We use spatial data analysis techniques to assess the relationship between county historical slave concentration and the black-white ratio of public school attendance. Our data originally come from the 1860 Census, 2006–2010 American Community Survey, and National Center for Education Statistics Private School Universe Survey, 2007–2008. Notably, our historical slave concentration estimates incorporate spatially informed refinements to better represent contemporary counties than previously available data. Drawing from our regression analysis, we argue that slavery history shaped the local social structure in a way that facilitates contemporary white disinvestment from public school systems. We examine two potential explanations for this legacy of slavery—the number of private schools and racial threat—particularly their manifestation within the Deep South. Despite evidence of subregional differences rooted in history, neither pathway explains the initial slavery association. We argue that processes tied to the legacy of slavery are a foundational component of black disadvantage and that further examination of this foundation is necessary to stem the tide of recent resegregation.