This historical analysis provided an opportunity to appreciate Chicago's course in the national school reform landscape. This study helped to understand the effects school reform efforts had on school leadership policy in Chicago. It verified a roster of superintendents in Chicago during 1983-2008, established a chronology of school reform events and assembled an inventory of reform policies, theories and directives that potentially may create the capacity to instruct and inform future initiatives, perspective and debate on the issue of principal preparation at the local level. The analysis of change in local policy echoed and identified national educational trends in this time period. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]