The focus of this research was to examine the effects of mayoral control on operational and financial structures within school systems. Furthermore, this study focused on the public perception and political implications of the mayor’s position on local education. The four systems chosen for this study were: Boston, Chicago, District of Columbia, and New York City. All four systems were total control districts, which allowed for each mayor to appoint a majority to the school board and appoint a superintendent or chancellor to oversee the day to day operations of the school district. This study focused on operational and financial structures, which make up a sizable portion of the larger organizational structure. These indicators often drive how services and expenditures eventually affect the core business of these school systems. From an operational perspective, this study was focused on expenditures, both in aggregate form and for instructional related services, pre and post takeover. From a financial perspective, this study focused on changes to revenue sources, return on investment, interest on school debt, and capital outlay. From a political perspective, this study examined the data from the various State of the City addresses over the last four years in each of the four cities, along with polling data available for New York City and the District of Columbia. This study was concluded with a summary of findings, and implications for future research, policy, and practitioners. The research showed that New York City and Boston generally outperformed the District of Columbia and Chicago in the operational and financial metrics used in the study. Furthermore, the number of years a city had been iv under mayoral control and operational and financial indicators had no significant relationship. It was recommended that future researchers should continue to study the benefit of benchmarking metrics of organizational performance to ensure mayors are held accountable for the reforms they espouse during election cycles. Ultimately, mayors’ success in managing their school systems will be based on where they prioritize. This research offered a cross section of metrics by which mayors can benchmark their effectiveness as they change operational, financial, and organizational structures to bring about better, overall organizational performance from their school system.