This book shares stories of historical figures from the past as well as contemporary school superintendents and principals. The present nature and complexity of leadership is heavily dependent on the past as we cannot fully understand or appreciate the current context without going back and exploring the past. To ignore great leaders from the past would run the risk of having current and aspiring school leaders not completely knowing understanding and appreciating these exemplary lessons the contemporary context. These stories help us to understand the values beliefs and morals of contemporary school leaders they help us define what it means to be a school leader in contemporary America. We can learn history in terms of stories either through telling stories or listening to the stories of others. But it is more than telling and listening. It is learning for not only those who wish to be school leaders but learning for those who currently are in positions of school leadership.