There is increasing interest in the early roots and influencing factors of leadership potential from a life span development perspective. This conceptual and empirical work extends traditional approaches focusing on adults in organizational settings. From the perspective of early influences on leader development, the goal of this study was to examine the effects of overparenting on adolescent leader emergence, influencing mechanisms, and sex differences. Students (N = 1,255) from 55 classrooms in 13 junior high schools participated, with additional responses from their parents, peers, and teachers. The results indicated that overparenting is negatively related to adolescent leader emergence as indicated by parent ratings, teacher ratings, and peer nominations in addition to leader role occupancy. The negative effects of overparenting on leader emergence (perceived and actual) were serially mediated by self-esteem and leader self-efficacy. In addition, sex difference analysis revealed that male adolescents received more overparenting and showed less leader emergence (perceived and actual) than female adolescents. Female adolescents' self-esteem was more likely to be negatively related to overparenting, and female adolescents' leader emergence (perceived and actual) was more strongly related to their leader self-efficacy when compared with male adolescents. Implications for life span leader development theory, for youth and adult leadership development practices, and for parenting practices on future generations are discussed. (PsycINFO Database Record (c) 2019 APA, all rights reserved).