Background/Context: The influence of non-school based venues has been historically significant for people of African descent who have often had to buttress their schoolhouse experiences with support from community-based influences. For example, Black churches, barbershops and athletic environments like basketball courts, and soccer and cricket clubs are particularly relevant for Black males in spaces like Bermuda and urban communities in the United States. Purpose/Objective/Research Question/Focus of Study: Drawing on a larger oral history project, this paper reports the findings of a secondary narrative analysis of a Black Bermudian male to provide an in-depth understanding of his in-school and out-of-school educational experiences, identity construction and success. The authors seek to answer the following research question: How does a Black Bermudian male describe the impact of his ethnic community for shaping his successful educational journey? Research Design: While the larger oral history study includes data collected from 12 Black Bermudian males, the scope of this article specifically focuses on the secondary narrative analysis of the experiences of one of the participants, Brandon Smith. As a published author, high-ranking civil servant, and prominent community leader, Brandon is arguably one of the most successful Black Bermudian males of his generation. Findings/Results: The results of the study reveal that the participant's educational success was undergirded by his exposure to varying constructs related to his personal and cultural identity; exposure to engaged educators, mentors, spaces, and opportunities in elementary, secondary, and post-secondary settings; and exposure to mechanisms of identity and success in the geographical spaces of Bermuda, the Caribbean, and the United States. Conclusions/Recommendations: Three subsections of the participant's exposure are discussed in the manuscript: nondeficit community and school-based exposure, multigenerational academically legitimizing support, and border crossing exposure. This study suggests that a Black Bermudian male can experience educational success when his educational journey inside and outside of school provides balance between his knowledge and acceptance of his identity. The authors contend that the schoolhouse is not the only space or variable that defines or prepares Black males for academic (or personal) success. Furthermore, many students who identify as African American in school may also have familial connections to the Caribbean, Africa, South America, Europe, Bermuda, and other jurisdictions. As such, educators should consider the significance of regional differences on Black male identities (e.g., North, South, East, West, Midwestern), and find ways to help students see relevance between their personal identities and larger causes and contexts.