Within a modern context, superintendents walk a fine line in today's reform minded, accountability centered, sociopolitical setting. To many, the position of public school superintendent is perceived as a job where failure is inevitable. The purpose of this comparative case study was to understand the factors that contribute to superintendent longevity in large urban school districts. This qualitative study focused on examining the perceived factors of leadership that contribute to the longevity of two superintendents in Southern California whose tenures have outlasted the national average. Using detailed protocols, these leadership factors were derived through extensive interviews with the superintendents, executive cabinet members, board of education members, principals, and surrounding area administrators. The factors found to contribute to superintendent longevity include an ability to build relationships that are authentic and strategic in nature, effective and thorough communication skills, a competent executive leadership team, personal leadership capacity, and a belief in the higher moral purpose of the daily work of a superintendent. [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.]