This study investigated the recent histories of the urban public school districts of St. Louis, Missouri and Cincinnati, Ohio in the United States of America. The purpose was to identify the similar challenges that each had recently faced in regard to the maintenance and development of its public school systems, as well to gauge the level of community support for the numerous reforms proposed by local education officials in each city over the past decade. After a critical review of the research and applicable theory, the authors offer suggestions for solidifying the future success of each system with examples of positive experimentation occurring in these cities and others. The city of St. Louis received the primary focus, as its enrollment and monetary problems tend to revolve back several years before similar issues surfaced in a comparable manner in Cincinnati. Each city was also examined in its particular historical context, with the accompanying educational, political, and social issues which have manifested themselves to the present state of affairs.