What if the reconstruction of Skopje happened today? What if, in the aftermath of the catastrophic disaster, the same unilateral call to solidarity occurred and the entire world came together in support of the city? What if leadership insisted on using this catastrophe as an opportunity to find new models for economic, infrastructural, political, and urban reconstruction? If that happened, what would architects, planners, policymakers, economists, sociologists, and other committed participants to reconstruction identify as the most pressing obstacles blocking a city from achieving recovery, unity, equity, and freedom? Based on the assumption that the fundamental ambition of the city is to enable freedom and prosperity for its citizens, we ask for each speaker to elaborated a view that addresses and defines the contemporary challenges that we must overcome and the future possibilities in order to enable freedom and prosperity for the citizens of a city. In essence, what are the potential new definition(s) for cities and the built environment?