Sport and recreation-based approaches to the social problems of "at-risk" urban youth have become very popular in recent years. Yet the lack of a proper theoretical understanding of these initiatives threatens to minimize their effectiveness and could generate a backlash against them. To begin to fill this void, this paper presents a case study--based upon several years of intensive fieldwork--of a Chicago teacher, coach, and grassroots activist and the community-based sports-oriented organization he heads. An examination of this sustained, grassroots attempt to use sport to keep urban youth in and interested in school and education is used to sketch the outlines of a deeper, more multifaceted theory of the possibilities and challenges of using sport as a mode of social outreach and intervention. (Contains 8 notes.)