Drawing on ethnographic research with homeless and street-involved youth in Vancouver before, during, and after the 2010 Olympic Games, this article offers a portrait of neoliberal urbanization as experienced by a city’s most marginalized residents. Taking as paradigmatic the aspirational goals of Olympic host cities to enhance their reputation as ‘global cities’, the article explores what this means for homeless youth through three processes: city cleansing, city marketing, and self-regulation. Examining how each of these are imbricated with policing and security practices, the article offers an in-depth look at how these abstractions are lived by homeless youth in the everyday. The article concludes by suggesting that marginalized young people are not the beneficiaries of Olympic legacies, despite promises made by organizing committees. In contrast, findings indicate that homeless young people are further marginalized by the Olympics, providing support for previous research that aligns mega-events with neoliberal outcomes.