This study examined how youths’ gender is related to the educational expectations of urban, low-income African American youth, their parents, and their teachers. As predicted, African American boys (ages 9–16) reported lower expectations for future educational attainment than did their female counterparts. Parents and teachers also reported lower expectations for African American boys (ages 6–16) than for girls. These findings held even when controlling for academic achievement. Contrary to predictions, the magnitude of the difference in expectations for males vs. females did not increase as a function of youths’ age. In keeping with our hypotheses, parental expectations fully mediated the relation between youths’ gender and youths’ expectations. Finally, certain school-based factors (i.e., positive teacher expectations and positive youth perceptions of the school environment) appeared to protect youths’ expectations from the deleterious impact of low parental expectations.