This qualitative, multiple case study investigated how educational leaders used and manifested Emotional Intelligence (EI) skills and abilities in unique organizational contexts. The study was conducted with five principals in a large, urban school district. The principals were selected to participate based on the organizational context of their schools. Each site was profiled and subsequently categorized based on the unique dynamics of the school including, but not limited to cultural, social, political, environmental, economic, and temporal factors. The principals were interviewed using a common, open-ended interview protocol. The interviews contained questions about the school's organizational context, the principal's relationships with stakeholders, and the principal's use of Emotional Intelligence (EI) skills and abilities in their role as the leader of the school. The interview transcripts were coded, analyzed, and compared with publicly available information about each school site to draw themes and conclusions to answer the research question: How do educational leaders exhibit and utilize EI within distinct organizational contexts? All five principals demonstrated evidence supporting the importance of EI skills and abilities in their role as principal and all five believed they could grow and develop their EI. The findings indicated differences in the use and manifestation of specific EI skills and abilities, from basic skills to advanced skills, across the different school contexts. This study was unique because it combined two, previously independent fields of study in the area of leadership: EI and organizational context. [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.]