This article examines the factors that facilitate and impede the academic achievement and social success of Black males in middle schools in the Bermuda Public Education System. Over the past decade, marginalisation, victimisation, and stigmatisation of this population have resulted in subpar academic and social success during adolescence. Fifty per cent of Black males fail to graduate from high school. It is imperative to heighten stakeholder awareness to ensure Black males are provided with educational and social opportunities that foster academic and social outcomes. Such opportunities will provide transferable skills to enable Black males to compete in the global market and to make meaningful contributions.