Superintendent turnover has been rampant in the public school district in Guam, an unincorporated United States territory; there have been 18 superintendents since the 1981. This qualitative study aimed to identify and analyze potential factors affecting the superintendency in Guam. Social systems theory proposes a number of factors about the dynamics that define the relationship between an individual and a social system to help us understand the behavior of the individual within an organization. To triangulate the data, this study was comprised of individual interviews with Guam superintendents and content analysis of the Guam Public School Audit of 2009 and subsequent amendments made to board policies after the audit. Based on social systems theory, major findings suggest that superintendent turnover in Guam is influenced by the following: the Guam Education Board did not understand its roles and responsibilities and often micromanaged the superintendents; the budgetary process for the Guam Department of Education was stressful and problematic; and political pressures from the legislature and the governor encouraged superintendents to take other roles. Suggestions for improving stability within the superintendency of Guam were offered by former superintendents. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]