The present study examined the development of a cohort of 279 early adolescents (52% female) from 1990 to 2005. Guided by the interactionist model (IM) of socioeconomic status and human development, we proposed that parent (G1) aggressive personality, economic circumstances, interparental conflict, and parenting characteristics would affect the development of adolescent (G2) aggressive personality traits. In turn, we hypothesized that adolescent aggressiveness would have a negative influence on G2’s functioning as an adult in terms of economic success, personality development, and close relationships 11 years later. Findings were generally supportive of the IM proposition that social and economic difficulties in the family of origin intensify risk for adolescent aggressive personality (the social causation hypothesis) and that this personality trait impairs successful transition to adult roles (the social selection hypothesis) in a transactional process over time and generations. These results underscore how early development leads to child influences that appear to directly hamper the successful transition to adult roles (statistical main effects) and also amplify the negative impact of dysfunctional family systems on the transition to adulthood (statistical interaction effects). The findings suggest several possible points of intervention that might help to disrupt this negative developmental sequence of events.