Youth mentoring organizations miss the opportunity to re-engage the people they serve to help others within their organization. As such, they may perpetuate the marginalization of the youth served. Through the Clark and Estes (2008) gap analytical framework, this study sought to understand the gaps in knowledge, motivation, and organizational influences affecting the re-engagement of alumni mentees. Further, using the lens of Bourdieu's (1986) social capital theory, this study first sought to investigate if the organization understood the personal gains of mentors in the relationship. Second, this study sought to understand if executive leaders understand the social capital gains for a mentee to advance to a mentor. This study employed semi-structured qualitative interviews, supplemented by a document analysis for triangulation of collected data. The validated gaps from this study were in motivation, organizational influences, and social capital understanding. The key findings from this study were in knowledge, motivation, and organizational influences, as well as in social capital. Most notably the participants indicated the social capital finding of mentors feeling like they receive more out of the match than the mentees. Certainly, if the organization encouraged alumni mentees to elevate to mentees, they too could receive this social capital gain. Further, encouraging alumni mentees could help the organization sustain itself with a cyclical mentor pool. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]