The purpose of this study was to add to the research on position longevity for urban school superintendents by examining personal character traits and skills. The study explores how these traits translate to leadership behaviors. Additionally, relevant background and experience necessary to success were examined. This was a case study involving one superintendent and the school district he manages. The work of Bolman and Deal (2003) provides the conceptual framework by viewing leadership behaviors through structural, human resources, political and symbolic frames. This study utilized a quantitative research design through the use of surveys to all Board of Education members, the superintendent's cabinet and all union officers. Qualitatively, the research design involved interviews with the Superintendent, a Board member, a cabinet member and a union officer. Another superintendent was interviewed to add interest to this study and to add validity to the findings. Information was garnered from interviews, but too few surveys were completed to make the quantitative results significant. Findings in this study examine those traits and skills necessary for the successful superintendent, as identified by superintendents themselves and those around them and serves as recommendations for post-graduate study programs or for those wishing to hone their skills. [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.]