This research is a study of the educational systems of South Africa and the United States in a comparative perspective. The research examines the success and failures of the two systems, taking black student dropout rates as a case study for understanding the structural, philosophical and public policy foundations of the genesis and development of the educational systems of the two nations. The two major areas of focus are Baltimore, Maryland and Mdantsane, South Africa, the high dropout rates in the case studies are employed as key explanatory variables to understand the factors behind the successes or failures of educational systems. The central thesis of the study is that the legacies of Apartheid and Segregation with public policies that do not fully address the root causes and symptoms the problems of poverty, low income and alienation of the students are associated with the challenge, the two nations face. A mixed approach methodology that integrates the theories, thoughts and experiences of published materials with statistical data derived from public and independent sources is employed in assessing the historical as well as the current records of education in the two case studies. The conclusion drawn from the study is that the very high association of negative historical legacies together with public policies that failed to address the causes and symptoms of the challenges, pose threats not just to groups and individuals produced by the system but also raise the national as well as global concerns of productivity, stability and human security. Specific policy and grass root level recommendations are offered for policy makers, all stake holders, and future research. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]