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.