There is a disdain for women in leadership positions in South African local government, and this can be attributed to manifold factors. Some of these factors may include distrust of women’s capacity or capability and leadership styles, flexibility and consultation in decision-making, issues of values and ethos, demography and social class, and political considerations in South African local government system. The objective of this article is to (1) explore gender roles in South African local government systems, (2) assess distrust of women in leadership positions in South African local government, and (3) explore how the male boss syndrome suppresses the creativity and efficiency of women in leadership positions in South African local governments. Data for this study were derived from female managements in several municipalities in the Northwest Province of South Africa. The findings demonstrate that innovation and a creative mindset are overlooked by male leaders in local government, simply because they emanate from a woman. Further, while women are hailed and acknowledged for their successes in business, science, technology, and innovation, and even have been considered for the presidency, at government levels, the sentiments are different, in that males in the sector consider the local parlance as a settlement for the liberation struggle. In conclusion, the transformation of gender relations may not be dramatic, but disruptions can quicken the process.