School superintendents make many decisions throughout their careers in an attempt to educate students. Many people, both inside and outside of education try to influence the decisions made by superintendents. Many of these influences are political in nature. This study looks at the history and levels of political influence in education, identifies the major participants in educational politics, and how the role of the superintendent has changed as political influence has increased in recent years. The study also looks at how superintendents make decisions to lead schools through the lens of the Transformational Leadership Theory. This study shows that collaborative efforts can tend to result in more political influence and make it more difficult to transform individuals and schools. The participants of the study explain how they balance collaboration with autocratic decision-making. Participants also explain how they navigate the politics of education through communication and political activism. By using social media to deliver their messages to stakeholders, superintendents can control political influencers. By becoming involved in the legislative process, superintendents can help bring common sense to new educational laws. The study also shows how much the superintendents dislike mandates from state and federal governments. [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.]