Leadership is everywhere in America. The concept of leadership is nearly impossible to define and means many different things to many different people, yet it permeates American society at all levels. Moreover, the American people seem to be obsessed with the notion of leadership, and within their obsession, have projected a value on the concept, making it a quality desired by many. The obsession of leadership is exemplified by the proliferation of the leadership industry and an increased emphasis on leadership development in the corporate world. Furthermore, higher education has been similarly affected by the leadership phenomenon and often aims to matriculate students with leadership experience and potential. Additionally, many collegiate institutions are now in the business of teaching leadership. Rooted in a curiosity about the leadership phenomenon in America, I raise some larger questions about the widespread teaching of leadership, namely, if the teaching of the concept is even necessary. My research is aimed at gaining a foundational understanding of what leadership is and an exploration of the effects of the phenomenon, as viewed through the lens of teaching leadership in higher education. I draw upon the conceptualizations of three leadership scholars; John Gardner, James MacGregor Burns, and Barbara Kellerman respectively to create a foundational framework for leadership. Although each scholar possesses distinct leadership views, there are commonalities which the scholars agree upon. Based on these commonalities, I provide an overview of three different case studies, each a different collegiate institution that teaches leadership. The case studies include, The Jepson School of Leadership at The University of Richmond, the United States Military Academy at West Point, and The Wharton School of Business at The University of Pennsylvania. The case studies help illuminate some of the problems that have emerged in our contemporary democracy in connection to the rise of the leadership obsession.