Skateboarding poses a unique case study for considering the place of sport in human activity. The bulk of skateboarding scholarship argues that skateboarding is largely a subversion of rule governance, a view difficult to square with common and popular rule-governed skateboarding competitions, now including the Olympics. We attempt to resolve this tension by arguing for a kind of pluralism: skateboarding’s engagement in rule-governed competition is distinctly subversive, yielding the claim that skateboarding is both sport and subversion. This pluralism is examined in an “ecological” framework of emergent activities defined by push-pull interactive relationships between skateboarders and their environment that change the meaning of their spaces—whether domestic, urban, or competitive—to spaces that are both wild and spontaneous. We conclude with reflections on how skateboarding provides understanding of sport in the space of ecological meaning.