Du Bois poses a poignant question in 1935 based on the logic that Black children need to be in schools where they are valued and inspired whether that environment is a separate school or an "integrated" school. This question of the effects of different educational spaces still begs to be answered in the changing landscape of secondary and postsecondary education for African American students and especially African American males. This article explores how increased choices, such as single-sex charter schools and for profit colleges, do or do not address the historical, educational, and social debt owed to African American males. Rhetoric and best practices associated with these choices are evaluated to inform recommendations for parents, students, communities, and universities.