What are the qualities of a good leader in a good democracy? The political developments of recent times, which have challenged well-accepted assumptions about leadership and democracy, lead us to return to that timeless question. This chapter argues that humility is an important virtue for leaders in a constitutional democracy. Humility is not arrogance, nor should it be mistaken for timidity or reticence. Instead, it is a quality that allows one to benefit from the knowledge of others, to learn from mistakes, and to work within a system of constrained powers. Calling upon the profiles of past leaders who possessed humility, such as Washington and Lincoln, the chapter argues that the possibilities for legitimate and effective leadership in a democracy are greater if the leader possesses humility. It concludes by questioning whether individuals currently in office have the qualities associated with humility and what its absence in current presidential leadership means for the state of democracy.