In recent years, skateboarding has been the subject of various attempts to sportify it. One of its most comprehensive definitions is "informal sport," which encompasses the various identifications like subculture, lifestyle, scene, and even delinquency. However, I argue that the proper ambiguities of skateboarding – when situated within specific power and cultural relationships – can assist in rethinking the rigid boundaries between some anthropological definitions of sport and play, the cultural politics behind the needs to categorize playing in sportive terms and the fragility of those labels when questioned by observing the practices of the participants. In Tijuana, bordering the ‘homeland’ of skateboarding (California), youth skateboard using scraps from U.S. skateboard factories that relocated south to the border after 1994 NAFTA approval. These circulate in informal markets, constituting the objects with which to practice and imagine a culture that is close but unattainable due to a regime of immobility. Discourses about marginality among Tijuana skateboarders highlights the lack of infrastructure, investment, and competitions that impede the development of local sporting champions. Concurrently, these communities endeavor to attract the California industry’s resources by presenting local skateboarding as a deregulated, exotic field untouched by money and professionalism: something more akin to urban play than sport, reappropriating 'authentic' U.S. imaginaries and selling them back to their original owners evoking nostalgia and purity. Through my long-term ethnography, I examine how skateboarders in Tijuana tactically mobilize the boundaries between sport and play in their efforts to gain legitimacy and resources in a context of uneven power distribution imposed by the border. In this frame, the institutional voices in charge to categorize sports and skateboarding emerge to be less relevant than the daily efforts of the skateboarders in navigating ‘sport’ and ‘play’ coherently with contingent collective urgencies, upsetting through practices the fixity of those categories.