In light of persistent Black-White achievement gaps for boys, this study examined publicly monitored risks believed to be associated with being behind academically for an entire subpopulation of African American boys in a large urban public school district. Also examined were indicators of academic engagement hypothesized to mediate the relations between risks and low achievement. Findings indicated that the Black-White achievement gap for boys was matched by a comparable difference in risk experiences. Multilevel linear regression models controlling for poverty found that both the type and accumulation of risk experiences explained a significant amount of variation in reading and mathematics achievement for the subpopulation of African American boys. Socio-familial risks were related to the poorest academic outcomes. Academic engagement indicators significantly mediated relations between risks and achievement. Implications of this research for collective school and community actions to make race, gender, and place matter in educational public policy were discussed. (Contains 7 tables and 1 figure.)