The purpose of this study was to examine and contrast the experiences of Black male scholar athletes at a Division I historically Black college/university (HBCU) and historically White university (HWU) and identify key contributors to their positive transitional experiences (academic, athletic, and social) in college. Two focus groups, 8 individual interviews, and an eight-item demographic questionnaire were conducted with 12 Black male scholar athletes. An anti-deficit achievement framework and critical race methodology were incorporated to better understand the processes by which participants' experienced positive transitional outcomes in two distinct racial, sociocultural, and educational milieus. Findings revealed key similarities as well as distinct differences in the navigational strategies and institutional influences that facilitated each group's positive experiences. Implications for policy and practice are discussed.