In comparison with healthy top-tier cities and those in abject decline, legacy cities are typically characterized as a middle ground where a complex mixture of assets and challenges provide the city with a unique variety of opportunities and hurdles. Proponents of legacy cities have constructed the term in an attempt to change the existing narrative around deindustrialized cities as a places of blight and poverty, instead re-framing the discussion around their unique challenges and distinct competitive advantage. In this paper, we interrogate the construct of “legacy cities” by examining how closely the original framework is captured by the operationalization of legacy cities used in recent literature and advocacy. To accomplish this, we use a technique called cluster-discriminant analysis, which groups metro areas according to their shared position on a number of theory-driven dimensions. This paper contributes to the literature surrounding legacy cities by 1) putting economic content behind the analytical framework by changing the geography from city to region, 2) demonstrating an improved method to better distinguish clusters of legacy regions according to the theoretically-rooted variables that drive them, and 3) structuring this method in such a way that places can shed their legacy status when revitalization occurs (an acknowledgement of successful recovery).