The current investigation tested predictions from the interactionist model (IM) of socioeconomic influences on the development of negative personality traits with respect to feelings of alienation and low well-being. The model tested proposed that lower family socioeconomic status would lead to fewer parenting and material investments in the next generation adolescent, which in turn would be associated with higher levels of adolescent negative personality traits. The IM also predicted a transactional process in which adolescent negative personality attributes would then deter future socioeconomic success during adulthood which, in turn, would hinder adult development in terms of greater feelings of alienation and diminished well-being. Analyses with a cohort of 347 adolescents followed for over 20 years produced findings consistent with these predictions. Moreover, additional analyses with 282 of the third generation children of these cohort members demonstrated that this same process was being replicated in the third generation. The findings suggest reciprocal or transactional influences that promote the development of negative personality attributes and accumulating personal, economic and social advantages over time and generations.