Despite the proposed ‘certainty’ in a city or region hosting a mega-event, there has long been issues of uncertainty surrounding the planning and implementation of what have until now essentially been mega-projects. Large events have found a variety of ways to adapt and respond to unforeseen circumstances due to political conflicts, planning of oversize venues, limited time of implementation, and legacies that are difficult to manage. Considering the further increased uncertainty surrounding the planning of mega-events as a result of the COVID-19 pandemic, this paper examines how an accompanying cultural component—e.g., the Cultural Olympiad—may help cities that plan for events like the Olympics transition toward diversified drivers and lon...