The leadership and career experiences of the principal in other eras are relatively missing from both the writings about school administration nowadays and the social history of schools. Exploring past forms of leadership might shed light on enduring aspects of leadership and its contextual-historical influences as well as on the development of early schools. This article explores the leadership patterns of Yehuda Antebi, a school principal who lived and worked in the area of Galilee (in the north of Israel today) in the first four decades of the twentieth century. His narrative provides insight into educational leadership in an emergent educational system and illuminates the link between the social historical contexts in which the educational leader works and his/her leadership patterns. In this sense, Antebi's story represents a sort of leadership that was less likely to have been influenced by globalization, marketization, and standardization, and thereby offers an opportunity to observe some patterns of educational leadership that are independent of current policies. The historical research is based, primarily, upon personal diaries (eight notebooks are extant today) that Antebi kept during most of his working life. They contain his reflections on his work experiences, feelings, attitudes, and correspondence and are to be found in a family member's possession. In addition, letters and speeches preserved by one of his sons were also used, as well as many letters and documentation found in the Jewish Education Archives (Federation of Teachers) at Tel Aviv University (file 5.203.6, years 1906-1925).