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Studies drawing correlations between Home Owners Loan Corporation “redlining” maps and present-day environmental outcomes have raised public attention about the role of systemic racial discrimination in producing uneven outcomes in the urban environment. In this analysis, we draw on a novel data source—narrative descriptions of neighborhood characteristics included in the area descriptions that accompanied City Survey maps—to explore the mechanisms that historically link HOLC maps and disparate environmental quality. Focusing on nine mid-sized cities in the Midwest, we draw on a combined inductive and deductive coding approach to consider how perceived urban environmental quality and neighborhood racial demographics shaped assessments of neighborhood value and risk. In doing so, we illustrate the ways in which nature, class, and race were already coupled at the time of the HOLC City Survey. The area descriptions in the HOLC City Survey illustrate the ways in which this coupling became codified and reinforced over time through housing and environmental policies, the impacts of which we still struggle to disrupt today.