n October 2017, shortly after violent clashes over the summer and the decisions of the city of Charlottesville, Virginia in The United States to remove monuments of the confederate generals Robert E. Lee and Thomas J. “Stonewall” Jackson, Ruth Ben-Ghiat wrote an article for The New Yorker entitled “Why are so many Fascist Monuments in Italy still standing?”. The article provoked outrage in the Italian press and more general perplexity at the cultural heritage practices of Italy. This paper, through a comparative analysis of The United States’ historic preservation law and Italy’s cultural property law, explores why a superficial parallel between confederate monuments in The United States and Fascist monuments in Italy is inadequate. It asks whether the discussions surrounding confederate monuments in The United States easily translate to the Italian territory. Indeed, a parallel between the existence of confederate monuments in The United States and the existence of Fascist monuments in Italy requires a profound consideration of a host of issues which surround these monuments as they exist in their respective countries and in their respective national cultural identities. These issues include the complexity of culture, legal nuances, and architectural and art historical narratives, to name just a few. The paper comparatively examines the two legal contexts in which the respective monuments find themselves, contextualizing specific monuments’ legal classification as historic property and cultural property, respectively, within the identity struggles and historical cultural heritage legal frameworks present in each monument’s respective country.