In light of the mechanics of the major election systems and their effects, we analyze how plurality rule has produced a two-party system on the Island and propose the preferential vote model to enable wider participation by the political actors as well as to enhance the public debate dynamics. While acknowledging that election reform is rare once a system has been established, the article seeks to circumvent resistance by avoiding a zero-sum analysis to reform and incorporating the winning political actors under the current system by presenting how a preferential vote scheme can also benefit them. In order to explore the elements necessary to trigger reform, we present an analysis of how Australia and New Zealand, two advanced democratic countries shifted from one election system to another and the reasons for reform as well as its consequences. If Puerto Rico is to pursue reform, proponents must understand the stakes of those winning under the current system and coin a platform capable of enhancing the democratic process by creating new spaces for debate and political representation while incorporating those who fear reform will lead them towards a path of power dilution.