This study focused on the interaction between specific obstetrical complications and early family adversity in predicting violent behavior during childhood and adolescence, in a sample of 849 boys from low socioeconomic areas of Montréal, Canada. Obstetrical complication data from medical records were used to create three scales using a nonlinear principal component analysis followed by rotation. Family adversity and teacher-rated physical aggression were assessed when the boys were in kindergarten and self-reports of delinquency were collected when they were 17. Elevated scores on the Deadly Risk Situation scale of obstetrical complications (preeclampsia, umbilical cord prolapse, and induced labor) increased the risk of being violent at both 6 and 17 years of age, only among boys who grew up in high adverse familial environments. Moreover, this interaction partly accounted for the continuity between violence in childhood and adolescence. Interventions for young pregnant women from deprived environments and their babies are discussed in light of these results.