This paper addresses the historic under representation of female superintendents. The primary focus is the legacy of discrimination, in which the barriers to female advancement in a traditionally male field are described. Particular attention is given to three different models of male dominance that have been developed to explain how and/or why women have been excluded from top positions in educational administration. In part two, recognition of the importance of women\u27s contributions to evolving theory in educational administration and a description of the feminine leadership model is offered, wherein women utilize flexible web-like structures, empower others, and prioritize children and learning. In conclusion, future prospects for women in the superintendency are discussed