Singapore's Westminster parliamentary system of government was adopted as a historical result of it being a British colony. In its post-independence constitutional development, the dominant People's Action Party political leadership had made a series of constitutional amendments to its original electoral system, introducing innovative schemes such as Group Representation Constituencies, Non-Constituency Members of Parliament, Nominated Members of Parliament and the Elected Presidency. These changes have resulted in an electoral system that is so different and divergent from the Westminster model that it should be regarded a unique regime of its own. This paper advances the view that the constitutional evolution of its electoral system is reflective of a political vision structured along elitist lines – underscored by a desire to restructure the voting behaviour of its citizens, and ensure predictability and the preservation of the status quo. It has been driven by paternalistic assumptions about what is beneficial for its citizens. This paper examines the subsequent implementation of the schemes, before reflecting on how it is a system that has the potential to affect adversely the development of political participation and political pluralism, and dilute democratic politics in Singapore.