The evolutionary theory of path dependency suggests that the longer an institution has been in place, the more resilient it is to change. Given enough time and self-reinforcing mechanisms, an organizational and institutional path develops and becomes highly resistant to change and likely to endure for a long time. Since the path benefits those who created it, the same actors cannot unlock it. Only an ‘exogenous shock’ (an event outside the path) can radically change the incentives or constraints facing the actors and enable a country to break free of the path. This article applies these propositions to explain the past, present and future trajectories of decentralization and local government (LG) institutional development in Ghana and Uganda. The article shows that Uganda pursued a sequence of political, administrative and fiscal decentralization whereas in Ghana the order was administrative, political and fiscal. As a result, Uganda has made a little progress, more than Ghana, in strengthening LG institutions. However, given that neither Uganda nor Ghana followed an ideal sequence of decentralization reforms that would have strengthened LGs against unbridled central government (CG) interference, currently CGs in both countries are retaking much of what was initially decentralized. The article concludes that recentralization and further weakening of LGs are likely to continue in both countries because the initial path that was created benefited CG politicians and bureaucrats and they are committed to staying on that course