In this study, we utilized a case study approach to examine the perspectives of 20 school stakeholders regarding equitable ways they promote and broaden the participation of Black male students in a high school academy of engineering (AOE). Madison River Academy (pseudonym) is a comprehensive high school with an AOE embedded in it. The ethnic and racial backgrounds of students at Madison River Academy are 68.8% Black, 14.4% Latinx, 8.7% White, 4.3% Asian, and 3.4% Multiracial. Three themes emerged from our data analyses of the school stakeholder interviews, including the following: (a) a cultural mismatch: denoting the cultural disconnect between teachers and Black male students; (b) math as a gatekeeper: symbolizing mathematics as a barrier Black male participation in the AOE; and (c) promoting equitable access: representing strategies the school stakeholders discussed that could address the equity issues within the AOE. More specifically, within the promoting equitable access theme, two subthemes emerged: building vertical pathways from middle to high school and applying science, technology, engineering, and mathematics (STEM) pathways. We provide recommendations for addressing the equity issues within our case study and promoting higher levels of participation of Black male students in the AOE.