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This paper presents preliminary results of life course interviews with 25 juveniles incarcerated as adults at SCI Pine Grove in Pennsylvania. The data collected in repeated in-depth interviews, through case file analysis, and in interviews with the original respondents’ friends and relatives, allow us to trace the development of negative turning points in these young men’s lives. Building on Sampson and Laub’s understanding of turning points (2005), we hypothesize that the teenagers’ pathways into severe criminal activity was shaped by contingent social processes in which individual dispositions interacted with opportunity structures in neighborhoods, schools and the family. This in-depth analysis thus seeks to uncover the mechanisms by which involvement in crime manifests itself at a young age. It particularly focuses on how environmental factors support or dissuade individual predispositions that have developed during early childhood (Moffitt 1993). The results presented are therefore relevant for creating more effective juvenile justice interventions. The data also aids our understanding of the lives of serious offenders and may allow us to discern the aftercare needed to minimize recidivism.