Teaching youths who affiliate with a gang can be a daunting task. Risk factors for gang membership often compound across life domains and affect pro-social connectedness, cause feelings of marginalization, and hinder life-skill development. Sports and physical activities that are structured within a positive youth-development framework provide an ideal environment to reengage youths who affiliate with gangs, and open the door to the development of life skills. This article offers suggestions for framing a curriculum, delivering content, and evaluating progress when working with gang-affiliated youths. A three-phase learning progression of responsibility development is outlined, based on Don Hellison's teaching personal and social responsibility model. This article also presents the processes and strategies that were used in one program to successfully reconnect gang-affiliated youths with their families, school, and the community; develop respect and responsibility; and facilitate withdrawal from gang affiliation. (Contains 1 figure.)