Today, managers, politicians, educators, and healthcare providers are highly skilled technicians who navigate modern systems. However, followers seek more than know-how; they desire moral leadership. Even leaders equipped with skills must make difficult ethical choices. This book connects philosophy to leadership by examining three representative texts from the history of philosophy: Plato’s Republic, Aristotle’s Nicomachean Ethics, and Niccolò Machiavelli’s The Prince. The leadership ideas contained in each one of these philosopher’s works were not only pioneering for their age but continue to be relevant today because they provide insight into the enduring questions of leadership. The book demonstrates the timeliness of the classical works by applying these philosophical approaches to historical and contemporary cases. This book is ideal for readers who are acquainted with philosophy and those who are uninitiated. The connections made between philosophy, leadership literature, and real-life leaders enable readers to appreciate how deeper reflection into the themes of leadership might merit scholarly attention and bear witness to the close union between the philosophy of leadership and the real world.