This article seeks to provide a critical analysis and understanding of the institution of chieftainship in Botswana. It looks at the institution of chieftainship starting from before colonization, right through colonization to the present day, post-colonization. It will be observed that interference with the institution started from colonization and continues to the present day. Consequently, this article weaves a discussion of the justification for such interference through an analysis of the status and powers of chiefs during colonization and their status post-colonization. The chiefs’ reaction to the encroachment is also covered, for the chiefs were not simply passive and co-operative while their powers were being taken away.