In recent years, there has been a growing awareness that not all decommissioned and obsolete real-estate assets can be recovered and reused. After the paradigm of urban growth, and following the paradigm of regeneration, a new paradigm seems to be looming on the horizon: the paradigm of shrinkage. Due to this change in perspective, discussions on the potential of demolition policies as an alternative to regeneration and reuse are gaining support in the debate about urban growth. In the United States, there are two on-going programs using demolition as their main tool for urban planning: the blight elimination programs and the flood buyout programs. The former foresees the demolition of abandoned and decayed real-estate assets, while the latter envisions the demolition and relocation of buildings within areas under flooding risks. Given their successful employment in the U.S., this paper evaluates the applicability of these programs to an Italian case, which is characterized by a different building heritage and different territorial conditions. Simulations of the programs’ application are made using two case studies: Lecce nei Marsi (Abruzzo) and Moncalieri (Piemonte). The results demonstrate the substantial feasibility of the blight elimination programs’ usage in Italy, while the flood buyout programs instead demonstrates major obstacles that may hinder its successful application.