In November 2020, Puerto Rico, currently a territory of the United States, held a referendum and the majority voted to become a state of the United States of America. Statehood is decided by the U.S. Congress in Washington, D.C. For the 2020 Presidential Election, the Democratic Party platform expressed support for Puerto Rican statehood. Although the official stance on the Republican Party is to support whatever choice the electorate of Puerto Rico votes on in their referendum, many party leaders and members of the Republican Party have spoken out about their opposition to supporting the statehood of the territory. I will be investigating why these party leaders and general party members are against its statehood by looking at the Republican Party’s ideologically derived positions rooted in conservativism and the electoral incentive perspective to not have Puerto Rico as a state. How do leading Republican Party representatives justify their position against the addition of Puerto Rico as a U.S. state? How can the members of the Republican Party’s position on Puerto Rico statehood be understood by both party incentives and disincentives on expected electoral outcomes? It is noteworthy to look at what causes this paradox between the Republican Party’s official stance on Puerto Rican statehood and party leaders’ open opinions on the matter.