The social and educational life risks associated with being a Black male in the United States are not novel concerns. However, researchers, policymakers, educators, and other stakeholders have yet to consistently identify programs and interventions that can mediate the inequities that confront young Black men. Some researchers have indicated that youth development programs can provide unique supportive educational and social opportunities for young Black males and other urban youth. In this study, the authors used qualitative analyses and ethnographic research techniques to examine the influence of an intergenerational urban youth development program on three young Black men. After more than a year of observation and several hours of interviews, three young men aged 16, 19, and 23 years old provided a vivid account of how this youth development program influenced their lives. Analyses were focused on three central questions: (a) what attracted these young men to this program, (b) why did they continue to attend the program, and (c) what perceived benefits did they receive from the program?