The purpose of this qualitative case study from archival material was to evaluate the degree of public transparency in the evaluation methodology and procedures of school superintendents of districts with student populations between 700 and 900 students in the State of New York. This study examined the language of the 71 superintendent employment agreements and school district websites as they related to superintendent annual evaluations, and the responses of 22 of 71 school districts regarding the evaluatory methodologies utilized in evaluating the district leader. Specifically, the questions that guided this study were: (1) What are the stated purposes and processes for the evaluation of the school superintendent amongst these districts as stated in superintendent contracts?; (2) In what ways are the "Essential Knowledge and Skills for Effective School Leadership" (2001) referenced in the evaluatory methodology and procedures of school superintendents?; (3) How do superintendents promote public transparency with regard to the evaluatory criteria in their evaluation?; and (4) What are the most common elements for evaluation listed in contract language and how do these criteria relate to the literature surrounding superintendent evaluations? The study found no explicit usage of the "Essential Knowledge and Skills for Effective School Leadership" (2001), the defined leadership standards for the State of New York in the evaluation process; that the process of evaluating the school superintendent is not highly transparent amongst these school districts; that there are disparate approaches and processes utilized by school boards in evaluating the superintendent; the literature surrounding superintendent evaluation is dated; and there is not an abundance of recent relevant research on the topic of school superintendent evaluations. The study concluded that the process of superintendent evaluation is not well articulated in New York State due to an ambiguous state regulation regarding superintendent evaluation. Standards driven evaluations do not feature highly in the evaluation process of school superintendents, and that the evaluation process is not highly transparent to stakeholders in the various school districts. [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.]