Abstract The purpose of this essay is to shed light on why the democratic developments in Botswana and Zimbabwe, despite their many similarities, have gone in very different directions. By the time of their respective independence, both countries proclaimed themselves democratic states. However, only Botswana succeeded in the transition, while Zimbabwe soon fell back into an autocratic regime. The method used is a comparative case study. By comparing the cases Botswana and Zimbabwe in according to five selected democratic variables, this method makes it possible to explain why only Botswana succeeded. The research questions are: How have Botswana’s and Zimbabwe’s respective democratic transitions happened? What factors have influenced and guided the direction of the democratic development in Botswana and Zimbabwe? The following democratic variables will guide the comparison: “Economic development”, “Market economy”, “Strong middleclass”, “External influences” and “Political leaders dedicated to democracy”.                 The results show considerable differences between the democratic transitions of Botswana and Zimbabwe as regards all the selected democratic variables. The comparative method thus proved to be an effective tool to explain the democratic development in the two countries investigated in this case study. However, these factors potentially just scratch the surface and, in a theory-developing spirit, more democratic factors can broaden the explanation even more.