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This qualitative case study focuses on how one near-peer college adviser uniquely supported historically marginalized students’ postsecondary aspirations in a large public high school in the Midwest. Through observations as well as student (n = 13) and mentor interviews, the study uses a critical lens to explore the role of non-dominant cultural capital in mentoring relationships directed at the transition to college. Results suggest a youth-centric and strengths-based perspective supported students because the mentor did not forsake her own cultural roots in the community. She served as a multicultural navigator and provides a model for transformative practices designed to both support college access, but to do so while dismantling practices which tell students they must assimilate to be successful.