The superintendent is the most visible figure in a school district and subject to the greatest stress and public scrutiny (Fullan, 1998; Jazzar & Kimball, 2004). The nature of the position is highly complex and requires a skilled leader to be able to navigate intricacies of public education (Byrd, Drews, & Johnson, 2006). Thus, the most important search a board of education will conduct is for its superintendent of schools (Glass & Franceschini, 2007). The research overwhelmingly supports the notion that factors with political implications influence superintendent tenure and longevity. However, research that demonstrates a statistical connection between apolitical factors such as various district characteristics, a superintendent's professional experience, and a superintendent's tenure and/or longevity is deficient in the literature. This is especially true in New York State. This research explored a selected set of political and apolitical factors that might potentially influence the tenure and longevity of a New York State school superintendent. There were 244 New York State school superintendents who participated in this study. The factors studied in this exploratory analysis included the district's catchment area population, student enrollment, percentage of students receiving free or reduced price lunch, percentage of students classified as special education, percentage of English language learners, location within the New York City Metropolitan Statistical Area, the superintendent's area of teaching certification, the grade level taught by the superintendent, as well as the superintendent's experience as a teacher, building-level, and district-level administrator. Select factors with political implications, such as superintendent turnover as a result of board of education trustee turnover, the hiring of internal candidates for the superintendency, and gender were also studied. Multiple regression analysis was used in this quantitative study to determine that tenure, internal candidacy, and board of education trustee turnover all have statistically significant unique effects on superintendent longevity. Overall longevity as a superintendent, gender, and internal candidacy had significant unique effects on tenure in one's current district. None of the apolitical variables in this study were significant predictors of tenure or longevity. The findings in this study indicated that female superintendents in New York State have longer tenures in their current districts than their male counterparts, and non-statistically significant differences in overall longevity. The researcher also concluded that internal candidates for the superintendency have longer tenures than those hired from outside the school district. [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.]