This essay focuses on the adaptive reuse of tobacco warehouses and factories along Tobacco Row in Richmond, Virginia, between 1980 and 2005. This work encompassed an impressive environmental strategy that ambitiously recycled existing buildings and infrastructure to new urban uses. Even while promoting salutary environmental and conservation goals, adaptive reuse, by definition, also pushes buildings away from their historic function and often away from their historic significance; buildings are adapted to new uses for which they were not built. This essay will explore the tendency of the adaptive reuse process to preserve the historic building even as it obscures the building's early history. In Richmond and throughout the United States, local, state, and federal guidelines for preservation and rehabilitation generally give primacy to building exteriors over interior plan, urban context, industrial technology, and the spaces of labor. In treating building façades as the primary locus of historical meaning, historic preservationists often efface the very history that they are charged with protecting. In considering the effectiveness of adaptive reuse, it is important to weigh more than simply what happens to building exteriors. We need to consider the extent to which these projects encourage a capacity for critical reflections on the histories associated with particular places. It is also vital to assess the relationship between those histories, our understanding of the world around us today, and our own agency as citizens.