The purpose of conducting this basic qualitative study was to more fully understand marginalized Black males' transformational learning experiences when engaged in mentor-mentee relationship programs. A review of the existing literature revealed that marginalized adult learners' engagement in collaborative education programs enhanced learners' sense of value and humanity. Narrowing the gap in the literature, the successful outcome of this study has augmented the knowledge base pertaining to at-risk Black males' matriculation to program completion. When fostering generative mentoring relationships, seasoned educators transferred knowledge, skills, and attributes to at-risk generations of learners. In constructing the framework of this study, transformational learning theory was supported by a critical race conceptualization. Considering that education is socially situated, learners' socio-economic and historical backgrounds were acknowledged. Black males' experiences were viewed through the lens of social capital, social justice, and social betterment. Therefore, a trans-disciplinary approach was applied as the best means of interpreting adult learners' emic expressions. In the education equation, legislators' role in directing policy has come to bear on the implementation of Black male initiatives. In terms of practice, education solutions for Black males must address systemic structural barriers. The data collection entailed semi-structured interviews. Participants' responses were derived from a protocol of pre-structured guiding questions. Inductive analysis, supported by manual and axial coding, was applied to the data collection. Based on the findings of the results of the analysis, five emerging themes were "envisioning the future," "personal accountability," "cultural perceptions," "communal investment," and "re-scripting the narrative." Recommendations for better facilitating the learning experiences of Black males will enrich the educational experiences of all learners. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]