Leadership education is a prominent component of youth programming. In their efforts to promote leadership development, most youth programs promote character development and teach interpersonal skills but fall short in teaching leadership because they fail to encourage the use of authority. In this paper, we present the stories of five late adolescent exemplars as a case study of youth leadership emergence through volunteerism. These youth demonstrated leadership by transitioning from participating in community service activities to becoming organizers of their own beneficent efforts. Through a qualitative analysis of interviews with these adolescent leaders, we present themes that were important to their emergence as leaders. We then discuss how these findings should be used to inform youth development programs that are designed to encourage youth leadership through volunteerism.