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's 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.