In the context of the developing generational divide in contemporary African-American social life, this study examines the not-for-profit organization, Aid to Children of Imprisoned Mothers (AIM), and its successes and challenges in transitioning youth to leadership. I examine AIM's organizational culture and its ability to transition youth -- its staff, volunteers and clients -- into leadership in partnership with the adult leadership of the organization. The mission of AIM is, "To inspire hope and empower children of incarcerated mothers through programs and services that lessen the impact of the mother's incarceration." Implicit in this mission is the development of leadership and decision-making skills of the participants in the program as essential to breaking the cycle of poverty and incarceration in the families and communities of the participating individuals. While the generation gap within the African-American community is one specific issue in the contemporary social context in which AIM operates, other issues such as negative social forces that reinforce a cycle of incarceration and poverty, as well as the educational and socio-economic gap between service providers and clients, also challenge its goal of meeting its mission. Children of incarcerated parents generally live in environments where substance abuse and criminal activity are common. With an incarcerated parent, the family unit is weakened in its ability to shield the child from factors that negatively the child's social development. AIM attempts to provide guidance and social support for the participants in its program to break the cycle of incarceration in the family and the community.