Racial equality in the United States educational system has long been and continues to be a source of debate. Specifically, the disparities between whites and other minority groups have been increasingly more critical. Blacks and Latinos consistently score lower than whites on standardized tests and academic course work. There have been several explanations given for poorer school performance by certain minority groups than whites. In this dissertation, I explore the black white achievement gap through the examination of one widely known explanation, oppositional culture theory. This research investigates the major tenets of oppositional culture theory and the contemporary multicultural navigator concept. Using a grounded theory method of analysis, I examine the connections between suppositions of the theory and black students in the Upward Bound academic achievement program.