From a sports competition to a global catalyst for urban and economic development, the Olympic Games have significantly influenced host cities. Governments have leveraged the Games to market their cities and promote urban regeneration, transforming underutilised spaces into economic and social hubs. While editions like Barcelona 1992 showcase the Games’ potential to elevate global status and urban infrastructure, others such as Athens 2004 highlight challenges in maintaining sustainable legacies. Consequently, increasing public scrutiny over negative environmental, economic, and social impacts has reduced the appeal of hosting the Games, leading to a reduction in candidate cities. In response, the International Olympic Committee introduced the Olympic Agenda 2020 to enhance the Games’ sustainability, credibility, and youth appeal. This book hypothesises that the Agenda’s urban-related measures, while innovative, face significant challenges in practical implementation. Focusing on Paris 2024 and Milan-Cortina 2026, it identifies inefficiencies and gaps, proposing solutions to enhance urban sustainability and better align the Games with local needs. This first chapter outlines the research framework, establishing objectives and research questions that guide the investigation. It sets the stage for a systematic exploration of the Agenda’s urban implications, practical decision-making challenges, and potential pathways for more resilient Olympic planning.