Although much has been written about the utility of applying Sameroff and Chandler's transactional perspective to the study of child psychopathology, relatively few researchers have used such an approach to trace the emergence of child problem behavior from infancy to adolescence. Using a sample of 289 male toddlers from predominantly low-income families, the current study examined associations between various forms of early child disruptive behavior, subsequent trajectories of maternal depressive symptoms over the course of 8 years, and adolescent problem behavior. Results indicated that early child noncompliance was the most robust predictor of more chronic and elevated trajectories of maternal depression, which in turn discriminated teacher and youth reports of adolescent antisocial behavior but not internalizing symptoms. The findings were consistent with transactional perspectives of developmental psychopathology that have emphasized the dynamic interplay between child and parent characteristics.