This paper examines the educational pathways of Black Bermudian males whose experiences with leaders in schoolhouse and community-based pedagogical spaces (i.e. sports, social clubs and neighborhoods) offer insights into how Black Bermudian males navigate conflicts between schoolhouse values and the ideologies espoused in community-based pedagogical spaces. The author argues that institutional actors (e.g., teachers and administrators) must recognize and respond to the impact of non-school based educative spaces on student academic success, particularly for minority males.