An impressive array of literature acknowledges the role of family members, friends, neighbors, and community institutions as rich resources of social capital which poor African American parents utilize in the collective socialization of their children. How parents access, mobilize, and deploy family and community-based social capital in resource-deprived communities for the social benefit of their children has been well documented. Yet, little is known about the challenges poor parents face raising troubled youth, particularly African American boys, when they are unable to generate social capital within their social network of family members, friends, neighbors, and community institutions to assist with raising their children. How do low-income African American parents raise troubled youth in disadvantaged communities when there are few resources of social support to draw upon? What strategies do parents use when they have exhausted and depleted their social capital? Drawing on three years of ethnographic field observations and multiple in-depth interviews with parents of pre-delinquent African American boys, this article examines how African American parents living in an impoverished African American community in New York City rely on the juvenile justice system, particularly juvenile confinement, as a parenting strategy. The findings suggest the need for alternatives to juvenile confinement and additional social support resources that can assist parents with parenting troubled youth.