The book examines tales from the Jewish tradition describing the emergence of leadership in several important communities in Israel's history. It focuses on the two famous Sage legends - the legend of the founding of Yavne and its protagonist Rabban Yochanan Ben Zakai and the legend of the establishment of the land of Israel's Rabbinic Presidency and its protagonist Hillel the Elder. The research follows these legends closely and discusses the historical reality which rises from them, and points to the two kinds of leaderships they represent. These forms of leadership are also represented in the Jewish Medieval Literature of Spain, Ashkenaz, Egypt and Kairouan in northern Africa.