This study provided a historical analysis of the 1968 court ordered desegregation of South Holland School District 151. The purpose of this case study was to examine, according to primary source evidence, how the superintendents grounded their decisions within the prevailing social, political, legal and educational conditions of the time. The researcher applied the leadership framework of Sergiovanni's Five Sources of Authority by identifying words and actions of superintendents that support a source of authority. This case study sought to identify how the decisions made, actions taken, and resulting changes created a new context for each succeeding superintendent to operate within. This case study also examined how each superintendent brought awareness to the board of the prevailing social, political, legal, and educational conditions of the time as the rationale for the need to develop policy and/or make decisions. An examination of the board's policies and/or decisions was made to identify what values were represented based on a superintendent's contextual descriptions of the district's needs. This study began with the early history of the Village of South Holland and examined the religious and political influences that guided the transformation to a suburban setting from a rural community. The study followed the development of South Holland School District 151; examined the factors that contributed to the charges of unequal treatment by the African American Phoenix community; and concluded with the process of desegregation and the impact upon the school community.