Demolition is a common fact of contemporary urban life, particularly in areas with aging building stock, rapid population change, or sudden transformations in land-use. Far from a natural or inevitable process, however, demolitions and their aftermath are intimately tied to the uneven production, destruction, and distribution of value in social and geographic space. This article argues that there are two main social categories that demolitions fall into: “rent gap” demolitions and “spatial fix” demolitions, each representing distinct but related moments in urban processes of capital accumulation and corresponding with either rapid redevelopment of land or sustained periods of land vacancy, respectively. The socioeconomic factors of community areas in Chicago have a great deal of influence on the patterns of demolition and redevelopment that occur, affecting what kinds of demolition occur where. In the context of cascading social and ecological crises, the forms of value that are legible to actors influencing the built environment, as well as accompanying practices of care and repair (or lack of it), call for urgent critical examination and reconsideration of demolition-neutral urban policy.