The International Olympic Committee (IOC) lacks candidates willing to host the Olympic Games (OG) and has reacted to this situation by introducing the Olympic Agenda 2020 (OA)—a reform process making the OG more attractive for potential hosts. This study analyzes whether the OA plays a crucial role for the future of the OG. We, therefore, examined the official IOC documents and feasibility studies of the 2026 Winter Olympic Games (WOG) bidders and conducted qualitative interviews with experts in the field (n = 15). The results reveal that the 2026 WOG hosts plan to reduce the budgets for the organization and the infrastructure costs in the host regions. As a consequence, the number and nature of the sites and venues as well as the distances between them will increase. This means that the future Olympic heritage (OH) may lay less in iconic buildings but rather focus on the attempt to fulfil the city’s long-term strategies. Our analyses extend the literature by: (1) analysing the OA in view of future OG, (2) comparing experiences from past OG with those of current bidders, (3) integrating expert knowledge thanks to qualitative interviews and, finally, (4) considering new heritage concepts.