In two mid-sized, southern cities, Nashville and Louisville, communities took vastly different approaches to public school desegregation. Where Louisville saw widespread success in fully integrating its schools, Nashville failed. Through qualitative research it is asked, "What are the most compelling explanations for the long-term failure of the desegregation of Nashville Public Schools in comparison to a successful desegregation model in Louisville?" The findings of this article suggest that many factors must be aligned for successful desegregation, including high barriers to White flight, a united activist front, and inclinations of federal judges. By understanding these factors, school boards in mid-sized cities in the South can continue to pursue desegregation in public schools.