The following study explored coaching behaviors and youth coaches’ justifications for their actions by comparing more effective and less effective coaches from an underserved setting. Reasons for their coaching behaviors were also explored. In-depth interviews and ethnographic observations were conducted with 12 coaches from 6 different youth sports. Support for each theme from the analysis was compared between the 6 more effective and 6 less effective coaches. Less effective coaches tried to create a sense of family within the team, but used very negative, militaristic coaching strategies that were not developmentally appropriate. Less effective coaches justified the negative approach because of the perceived dangers in the inner city and attempted to toughen their players through harsher methods. More effective coaches challenged players while being supportive, attempted to develop close relationships along with a positive team climate, and promoted autonomy and the transfer of life skills from sport to life. More effective coaches appeared to be more open to coach training and others’ ideas—they could be described as lifelong learners. The results from this study not only reveal how more and less effective coaches differ, but provide possible insight as to why they differ. The study provides unique insights for researchers and coaching educators interested in particularly underserved settings and in developing less effective coaches.