While the fields of leadership theory and queer theory are independently robust in scholarship, little research and writing exists bridging the two. On the surface it may appear that this fact is logical, with leadership theory and queer theory possibly having little to do with each other. More so, as leadership is a normative activity and queer theory holds an antinormative commitment, the two may even seem contrary. There are leaders in higher education, however, that paradoxically hold commitments to queer theory. This dissertation bridges the gap between the two fields and explores the paradox of queer leadership, ultimately producing a new theory of leadership, grounded in the experiences of queer leaders, called Leading toward the Margins. Queer theory and leadership theory are first connected through an analysis of the history of sexuality and its relationship to the development of contemporary leadership theories. Then, through a qualitative research study, utilizing a grounded theory methodology, the lived experiences of queer leaders in higher education—defined as senior administrators with an academic relationship with queer theory—provide the data from which a theory of Leading toward the Margins emerges. Leading toward the Margins is an innovative approach to leadership for higher education that is defined by six key categories: Understanding Structures/Systems/Norms, Positionality and Subjectivity, Oppositionality, Commitment to Change, Creativity and Idea-driven, and Transparency and Collaboration.