This article examines how the political structure of school elections contributes to leadership perspectives related to school-community engagement. Interview data from school superintendents, school board presidents, and city mayors across four cities and two election types were analyzed to determine if differences in school election structure are reflected in leadership perspectives. A leadership typology of professional, political, and engagement decision making was used in the analysis. Data indicate that stronger school-community relationships exist where the politics of the election process has not been minimized. Findings have implications for educational policy relating to public school governance. (Contains 3 notes and 2 tables.)