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This qualitative case study, based on data outcomes from a larger project, examines the relationship between positive racial identity and the pursuit of post-secondary education among male Black students in Ontario, Canada. Using a phenomenological approach, this study sought to understand through the stories shared during qualitative interviews, the factors participants believed facilitated their sense of positive racial identity, what contributed to their commitment to pursuing post-secondary education, and the challenges they experienced in the process. The qualitative analysis revealed that Black male students who reported having a positive racial identity (PBRI) were more likely to report experiencing multiple positive benefits including academic persistence, an increased sense of self-worth, self-competency, and the ability to withstand barriers and stereotypes.