The once all black Howard High School in Wilmington, Delaware, has had a long and interesting past. For more than a century, the high school attempted to maintain a strong academic core amidst pressure from the white community to become a vocational or "industrial" school, following the Tuskegee model. In this article, the author discusses the history of Howard High School and examines whether the academic or vocational focus made more sense for the graduates of Howard High School in the late school segregation period from the 1930s through the 1950s.