In front of opposition to her leadership from the religious institution in her country, mainly due to her gender, Benazir Bhutto, the Prime Minister of Pakistan in 1988–1990 and in 1993–1996 focused on democratization and the liberation of women in Pakistan. This chapter analyzes Bhutto’s leadership and emphasizes her battle for women’s equality and emancipation and for democracy, coupled with determination and compromise. Her story reflects the constraints female leaders in many developing countries face while attempting to introduce liberal and democratic reforms, even to a limited extent. Her leadership provides us with much insight into the components of constrained democratic educational leadership such as compromise, democratic school climate, and freedom of thought and action.