The aim of this article is to attain insight into the issues of empowerment and motivation in principalship in general and in feminine leadership at schools in particular. It presents a case study of a woman principal who "bred" 12 principals during 12 years of principalship, most of them in her last 5 years on the job, in the middle of the 1990s. This case study is based on data collected during 3 years, during which the author was deeply involved in her school as an organizational consultant. The principal investigated is part of a constantly growing majority of women principals in Israel in the state-secular Jewish section. The analysis focuses on the gender aspect of leadership and mentoring in education. In this article, the author deals with two questions: First, how did the principal behave as a leader? Second, how did she act as a mentor of potential principals? Following the introduction is a discussion of relevant theories regarding principalship, leadership, and mentoring. The author then presents the study and its findings. Finally, the author links findings with theory and emphasizes the unique contribution of this study to the understanding of leadership and mentoring in education.