School district leadership matters, as evidenced by a meta-analysis of 27 reports and 1,210 districts conducted by Waters and Marzano (2006) which highlights a statistically significant correlation between district leadership and student achievement. Because this relationship is significant, it is important for school districts to have effective leaders who have the necessary knowledge, skills, and behaviors to serve their students and communities for a consistent period. Although consistent leadership at the apex of a school district is critical to its overall success (Ray & Marshall, 2005), additional studies (Glass, Bjork, & Brunner, 2000; Council of Great City Schools, 2010; National School Boards Association, 2001) indicate that the average tenure of school superintendents is less than six years. This qualitative study utilized semi-structured interviews of seven long-standing large district superintendents in an effort to determine the perceived factors associated with their longevity. Three theoretical frameworks, Callahan's vulnerability theory (1962), Eaton's cumulative theory (1994), and Lutz and Iannaccone's dissatisfaction theory (1986); served as the lens for the study. The findings from the five research questions resulted in multiple categories reflecting the following themes: (1) emphasis on instruction and needs of teachers, (2) ability to develop and maintain relationships with internal and external public, (3) clear governance and communication structures with board members, (4) political connections, and (5) organizational management structures. [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/en-US/products/dissertations/individuals.shtml.]