This thesis will examine Washington, D.C. as a test case for effective education reform with a focus on the leadership of Michelle Rhee, former Chancellor of D.C. Public Schools. Rhee’s leadership is of particular interest because she served in an unusual political and institutional setting in which D.C. Mayor Adrian Fenty gained mayoral control of the school district. This paper examines Rhee's reform efforts with respect to the bureaucratic limitations and institutional confines she faced, as well as the resources she had at her disposal. The results of this test case strengthen the arguments of scholars like Rick Hess and Terry Moe, who assert that the foundational structures of the American public school system are not only outdated but broken. Additionally, Michelle Rhee's struggles as Chancellor legitimize elements of the arguments of education policy expert and historian Diane Ravitch, a strong defender of the traditional structures of the nation’s public school system and their contributions to the country's fundamental democratic principles. This analysis of education reform in Washington, D.C. acknowledges that Rhee achieved numerous small victories over the course of her tenure, but she lacked the capacity to fix larger systemic obstacles on her own.