This retrospective study used the language of political ecology to describe the dynamics of a school board decision to hire a nontraditional superintendent. Those dynamics were described as contextual variables that existed within the community as well as mediating variables that were negotiated among the key players who were part of the selection process. This study confirmed that the school board did not make the decision in isolation from the community power structure. The methodology of this descriptive case study was qualitative, using a basic interpretive design informed by symbolic interactionism. Data were collected primarily through interviews with key players of the superintendent selection event, as well as from local news articles and artifacts. This research identified variables that were part and parcel of the superintendent selection process. It also helped to explain why most of Jacksonville, Florida, favored a candidate with a military background over three other candidates who had served as superintendents of other large, urban school districts. The environmental and mediating variables were presented as key constructs that affected the superintendent selection process and influenced the final decision to hire a nontraditional superintendent.