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The Olympic Games have evolved from a sporting event into a perceived catalyst for urban transformation, enabling host governments to pursue legacies that position cities as global hubs. Yet aligning the Games' demands with urban planning goals remains challenging. Mounting public scrutiny of rising costs and risks has reduced enthusiasm for hosting, prompting the International Olympic Committee to launch the Olympic Agenda 2020, aiming to enhance sustainability, credibility, and youth appeal. This book critically examines the Agenda's urban measures, focusing on preparations for Paris 2024 and Milan-Cortina 2026, the first editions fully shaped by them. Findings expose persistent gaps between global ambitions and local outcomes, rooted in structural dynamics of both the Olympic model and host city systems. By proposing mitigation strategies, the book advances debates on mega-events, offering resilient approaches to better align Games planning with host cities' needs and strengthen urban sustainability for future editions. Gustavo Lopes dos Santos holds a PhD in Territorial Engineering at Instituto Superior Técnico (IST), University of Lisbon (Portugal). He is interested in the study of the dynamic interrelationship between the city and (mega-)events, regarding the planning, delivery, and permanent and temporary effects in territories and communities. Beatriz Condessa is assistant professor at Instituto Superior Técnico (IST), University of Lisbon (Portugal). She teaches and researches in urban management, focused on the integration of urban planning, law and urban economics, and she has special expertise on application of equity in land use planning. Fernando Nunes< da Silva is a retired full professor of Urban Planning at Instituto Superior Técnico (IST), University of Lisbon (Portugal). He participated regularly in courses of urban mobility and transportation and taught in several European and Brazilian Universities. Marie Delaplace is a retired full professor in planning and regional development in the Parisian school of urban planning (EUP, Gustave Eiffel University, France). She co-manages the observatory for Research on Mega-events (ORME) which deals especially with the Olympic Games (Paris 2024).