The purpose of this study was to examine the importance of the student-faculty mentoring relationship from the perspectives of a Black male doctoral student in music education and his White mentor/professor. A specific focus of this study was the development of trust. Previous studies with doctoral students have identified trust as a key component in the success of interracial research/academic mentoring that leads to enhanced intellectual self-concept and, eventually, degree completion. Data consisted of structured interviews, participant-authored questionnaires, with two post-coding conversations between the participants to determine themes and findings. Codes were drawn from previous research in another field; these were revised to reflect the contextual nature of the individuals in this study. This report centers on applications of the data corresponding to four broad themes: (a) contributors to trust; (b) reasons for mistrust; (c) critical consciousness; and (d) the benefits of cross-racial mentoring. Though the study was situated in music education, very little of the data reflected the field of study but, rather, the specific challenges of navigating the academy. Findings indicate that both the student and the mentor experienced elements of racial stress and cultural isolation in an otherwise supportive collaboration.