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This essay explores the background to the organization of the 1928 Olympic Games, and the impact of hosting the Games on Amsterdam's position as a city of prominence in Europe and indeed the world. Going back to the founding days of the City of Amsterdam, the city's heritage will be used to provide a platform for more recent political rhetoric and actual policy plans for Amsterdam to potentially bid for the 2028 Games, 100 years since the first time they hosted the event. Next to (part) speculation on why Amsterdam should or should not bid for the Olympics again, the essay will take a comparative perspective, evaluating both the 1928 and 2028 cases to identify if reasons for wanting to organize the Olympic Games are based on similar or quite different legacy intent and if legacy intent is founded upon distinguishing features of the city's heritage. [ABSTRACT FROM AUTHOR]