This study provides a historical analysis of the Chicago Public Schools major reform policies and initiatives and their implications for educational leaders and principals in urban areas during the mayoral term of Rahm Emanuel. This analysis includes detailed reform initiatives implemented under several mayors and CEOs leading up to Mayor Rahm Emanuel's terms. It gives an account of the effects those reforms had on educational leaders' (principals) ability to implement them and informs future educational leaders on the challenges and success they may face while implementing school reform initiatives. The results of this study indicate that the extended school day, the new teacher evaluation, the Star Program, and universal full-day pre-kindergarten initiatives are the most successful and promising policies for urban school leaders to consider implementing, while privatization of schools and principal merit pay is found to be less effective. Privatization, in and of itself, does not appear to be an effective initiative as continued by Mayor Emanuel. However, the closings and shake-ups, which involved both privatized schools and district-run schools may be effective in contributing to increased student achievement because it allows the examination of underperforming schools. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]