ABSTRACT This article explores the unintended impacts of an immensely popular and far-reaching preservation program, the National Register of Historic Places, which was established to instill a sense of stewardship for heritage at a time when suburbanization and urban disinvestment threatened its existence. Anointing neighborhoods as “historic” has helped preserve them, but it has also increased market demand and facilitated gentrification. Drawing on census and preservation data, we use principal component and cluster analyses to identify neighborhoods in Chicago experiencing physical upgrading and the displacement of groups of lower socioeconomic status. Particular interest is placed on exploring neighborhoods characterized by gentrification and intensive preservation activity. The diversity in heritage-driven redevelopment processes and gentrification is then examined within three neighborhoods. The study reveals that preservation has not kept pace with changing demographic, housing, and consumption patterns within cities: a counterproductive policy lag exists, facilitating large-scale residential displacement of traditional urban populations, ranging from the most marginalized to the wealthier.