This research investigates the social reproduction of inequality by drawing on prospective longitudinal data from three generations of Youth Development Study respondents. It examines intergenerational influence on the relatively unexplored academic self-concept as well as educational plans, a critical component of the status attainment model. A structural equation model, based on 422 3-generation triads, finds evidence that the sources giving rise to the development of children's (Generation 3) achievement orientations do not only result from parental (G2) contemporaneous influence. Prior influences implicate grandparent (G1) educational attainment and income, grandparental expectations for the G2 adolescent, the G2 academic self-concept and educational plans measured more than twenty years earlier (in G2's adolescence), and G2 educational attainment. A familial culture emphasizing academic self-confidence and high educational expectations may be an important component of "family capital" that supports educational attainment and contributes to the maintenance of social class position in each successive generation.