The Kuwaiti Constitution of 1962 created an interesting hybrid political system, combining a hereditary executive and a freely elected national assembly. To this end, the political history of Kuwait has been one of a game of power balancing between the unelected executive and the elected national assembly, causing recurring political gridlock. At the heart of this game of power balancing is a struggle over the nature of the electoral system and electoral districts. The executive in Kuwait sought to manipulate electoral districts and the electoral system to its advantage, but has generally been unsuccessful in controlling the outcomes of elections to the national assembly and has not been able to quell opposition. Yet what is more surprising is that even when the opposition managed to push back and force its own electoral law and districting scheme, it was not entirely successful in dominating the national assembly. The result was a continuation of the gridlock that characterized Kuwait’s political system since its inception in 1962. This paper seeks to identify the factors that have led to a political system characterized by perpetual gridlock in Kuwait, through an examination of the crucial battle over the electoral system. The study aims to expand on the literature concerning nominally democratic institutions in autocratic regimes in order to explain the strategies of dictators in controlling the opposition, and ultimately, at what point those strategies fail. Such an analysis demonstrates that even the failure of manipulating nominally democratic institutions does not necessarily lead to democratization. Rather, political gridlock becomes the status quo – confounding scholars who have viewed such institutions as either state-subverting or state-sustaining.