Scholars often consider the Brown decision of 1954 as the chief legal victory for African Americans in the twentieth century. Although the National Association for the Advancement of Colored People’s legal team achieved their goal of gaining access to public education for black citizens, historians studying this movement generally praise the outcome of Brown while not focusing on the unintended consequences of that victory. Such circumstances as the ultimate demise of many southern-based black institutions in the name of integration. Researchers have often labelled the leaders of such institutions as obstructionist, gradualists, accommodationist or even worse, “Uncle Toms.” Much of this criticism came from individuals who did not carry the burden of leading either a southern-based institution or community during the early 1900s. Despite these negative labels, black college administrators such as Shepard were responsible for creating a southern black professional class, and future Civil Rights leaders through their institutions of higher learning. Consequently, this essay will explore how Shepard navigated the currents of southern white supremacy, and northern black radicalism while creating an institutional legacy that remains today despite his “gradualist” approach during the long Civil Rights Movement.