Social learning theory has enjoyed decades of supportive research and has been applied to a wide range of criminal and deviant behavior. Still eluding criminological theorists, however, is a meaningful understanding of the causal processes underlying social learning. This lack of knowledge is due in part to a relative reluctance to examine value transmission as a process in the contexts of mentorship, role modeling, and social learning. With this empirical gap in mind, the present study seeks to isolate and classify meaningful themes in mentorship through loosely structured interviews with young men on the periphery of the criminal processing system. The purposive sample is drawn from youth in a Southwestern state, living in a state-funded, privately run group home for children of unfit, incarcerated, or deported/undocumented parents. The youth included in the study have recently passed the age of eighteen, and have elected to stay in the group home on a voluntary basis pending the completion of a High School diploma. Further, both the subjects and the researcher participate in a program which imparts mentorship through art projects, free expression, and ongoing, semi-structured exposure to prosocial adults. This study therefore provides a unique opportunity to explore qualitatively social learning concepts through the eyes of troubled youth, and to generate new lines of theory to facilitate the empirical testing of social learning as a process. Implications for future research are discussed.