Urban Head Start graduates were compared with comparably poor Pre-K graduates in this longitudinal study, in an effort to evaluate the long-term effects of the Head Start program. A sample of 227 children were included in an analysis of third-grade report cards, standardized Comprehensive Test of Basic Skills (CTBS) achievement scores, and a standardized assessment of development (Vineland Adaptive Behavior Scale). The results indicted that although Head Start does not bring children up to the level of average third graders, when contrasted with comparably poor Pre-K graduates, Head Start results have some surprising affects on children about to make the transition to fourth grade. Maladaptive behavior in Head Start graduates is lower, suggesting more adequate mental health in this group of children compared to other very poor children. Although these Head Start graduates had some difficulty with language expression (CTBS) and its functional use, they were generally more successful than other poor children in making the transition to fourth grade and in meeting academic demands of the later childhood grades. In general, results suggest that when Head start is done well, it can have an extended impact on educational transitions in its graduates' lives, even if those graduates are African American children in an urban school system. (AA)