This paper explores skateboarding as an opportunity for sustainability-related diplomatic and place-branding opportunities in the Olympic Games and its host cities. The rise in popularity of skateboarding also makes it a highly visible example of how the Olympics can turn, or conversely, exacerbate, the environmental footprint of the Games. We explore two main lines of inquiry: How might the inclusion of skateboarding in the Olympics mark a turning point for a ‘greener’ image of the Games? And: how can skateboarding facilitate a minimalist and adaptable approach to conducting sport events more sustainably by using a city’s already existing infrastructure?