This study examined the ecology of “free gym” as it occurred in both school lunch hour and after-school community settings. In an effort to understand how urban youth experience sport, an ethnography using multiple methods was conducted to ascertain how urban youth shape their own cultures according to the social forces operating within the gymnasium. A period of sustained observation revealed a student-imposed hierarchy that was dominated by skilled male African American basketball players. Status was gained through what occurred within the free-gym ecology. Students often had to learn the system by “serving time” before they could join a desired level of the hierarchy. While a few students thrived in this environment, most merely survived or were marginalized. Such a setting has implications for how physical education and school culture is subjected to wider societal influences. The presence of socially chronic situations such as free gym require a pedagogy that is more democratic and more enriching, thereby moving from the real toward the ideal.