Increasing attention is being paid to the question of why some people emerge as leaders, and we investigated the effects of persistent exposure to poverty during childhood on later leadership role occupancy. We hypothesized that exposure to poverty would limit later leadership role occupancy through the indirect effects of the quality of schooling and personal mastery, and that gender would moderate the effects of exposure to poverty and personal mastery. Using the National Longitudinal Study of Youth provided multiwave and multisource data for a sample of 4,536 (1,533 leaders; 3,003 nonleaders). Both school quality and personal mastery mediated the effects of family poverty status on later leadership role occupancy. Although gender did not moderate the effects of poverty on leadership role occupancy, the indirect effects of early exposure to poverty on leadership role occupancy through personal mastery were moderated by gender. Conceptual and practical implications of these findings are discussed.