The relationship between skateboarding and the city has always been ambivalent. While skateboarders are deeply connected to the city as an architectural, social, and symbolic space, they are also repeatedly subjected to attempts at displacement. But why is the relationship between skateboarding and the city so challenging? What significance does urban space hold for the practice of skateboarding? Conversely, does skateboarding have relevance for the city as well? How does a skate novice become an accepted member of the skater community? How do skateboarders learn their complex maneuvers? What role do media play in this? And is skateboarding really as political as some critical newspaper articles suggest? Based on more than six years of field research, the study provides insights into the development of skateboarding in Cologne. The author outlines the many facets of this relationship.