The present study explored how relationships with natural mentors may contribute to African American adolescents’ long-term educational attainment by influencing adolescents’ racial identity and academic beliefs. This study included 541 academically at-risk African American adolescents transitioning into adulthood. The mean age of participants at Time 1 was 17.8 (SD = .64) and slightly over half (54%) of study participants were female. Results of the current study indicated that relationships with natural mentors promoted more positive long-term educational attainment among participants through increased private regard (a dimension of racial identity) and stronger beliefs in the importance of doing well in school for future success. Implications of these findings and directions for future research are discussed.