This study explores cross-cultural career mentoring experiences of African American male protégés and their mentoring relationships with White male mentors in majority culture organizations. The central research questions examined in this study focused on whether formal matched cross-cultural career mentoring relationships involving White male mentors and African American protégés provide effective career and psychosocial development functions to those protégés. Two semi-structured in-depth interviews were conducted with each of the five protégé-respondents in this study. During these interviews, the researcher focused on the protégés’ childhood, family work ethic, social class, educational attainment, and neighborhood. Also, major career-related themes emerged from the semi-structured in-depth interview data: early shock phase, growth phase, and organizational relationships and connections. After reporting the results to this study the researcher discusses several scholarly and practical implications, as well as recommendations for future research. Extended interviews were concluded with each of the protégés’ mentor for informational purposes only. These interviews allowed the researcher to confirm and gain a better understanding of the protégés and self-reported mentoring experiences.