This paper explores the evolution of neighborhood revitalization and historic preservation in the City of Baltimore, and assesses the extent to which these practices reflect lessons learned from failed policies of the past. A long history of urban interventions in Baltimore has repeatedly disrupted the city landscape and calcified spatial inequality. Planners today acknowledge this history and have purportedly adapted the planning process to avoid repeating these mistakes. This study examined three modern neighborhood revitalization programs: the Sandtown-Winchester Neighborhood Transformation Initiative (c.1990), Oliver neighborhood revitalization (c.2004), and Project C.O.R.E. (2016), and determined that these changes have not been fully embraced in practice. Given the continued need to adapt planning practices to promote equity in neighborhoods harmed by previous interventions, this study concludes with recommendations for ways that preservationists can be better advocates for historic neighborhoods and their residents in the neighborhood revitalization process.