The study examined the life histories of 31 homeless male drug addicts. Their retrospective reports linked personal history and social circumstance to describe common pathways associated with and emerging from adolescent delinquency and drug involvement. Their accounts, framed within the social development model, indicate that the life chances of teens at risk might improve if policy-based solutions and interventions target and ameliorate contextual and interpersonal risk factors interfering with the accumulation of social capital. Substance abuse is an issue that needs special attention. The article concludes that improved family relations, friendships, school experiences, and social encounters can contribute to productive social development and desisting from delinquent behavior over the life course, increasing an adolescent’s chances of becoming a productive, contributing member of society. Notes, references