Recent scholarship has put Yugoslavia at the heart of the debate over the architectural production and urbanism of the Cold War era. To contribute to the inquiry into the architecture of former Yugoslav federation, I examine in detail the urban environment of Skopje-the capital of the former Yugoslav Republic of Macedonia-and its relationship with socio-political transformations of the last sixty years. Existing scholarship mainly focuses on the United Nations-sponsored reconstruction plans for the city after the catastrophic earthquake of 26 July 1963 that involved such internationally known architects as Kenzo Tange and Constantinos Doxiadis. A secondary focus has been the creation in the 1970s of monumental brutalist structures that have come to define the city. While architectural historians mainly study the events of the twentieth century, socio-cultural anthropologists explore the problematic of Ottoman heritage and ethno-national divisions of the present-day era. My project links the two fields and connects the two distinct periods that built Skopje, further exploring its idiosyncrasies. I argue that the study of the Macedonian capital reveals yet another facet of Cold War architecture and its impacts on the contemporary urban production as negotiated and mediated in a unique geopolitical environment. Through examination of the remodeling of communist Skopje and the city's present-day nationalist-driven alteration, I show that the 1960s post-earthquake reconstruction-that took place under the auspices of the United Nations and Yugoslav government-was an event that impacted the construction of modernist Skopje, but that it does not exist as a singular moment in the creation of the city's urban identity. I contend that the creation of the urban fabric of Skopje has been a multi-event process, entwined and nuanced. I argue that the collaborations between Kenzo Tange, Constantinos Doxiadis, Adolf Ciborowski and Yugoslav architects and planners such as Georgi Konstantinovski, Marko Mušič, and Janko Konstantinov were much more complex than previously understood. Finally, I claim that the treatment and negotiations of Ottoman heritage in the postwar and post-socialist nation-building projects in Yugoslavia and Macedonia-strikingly exhibited in the Skopje 2014 project-display the creation and negotiations of a distinct urban and national identity of a socialist and post-socialist state in the Balkans. The study of the architecture of Yugoslavia and its post-Yugoslav region provides further insight into the unique urban production of a country that spanned the Iron Curtain. Skopje is exemplary of the political and architectural complexities of the Cold War era and its contemporary aftermath in Southeastern Europe.