Puerto Rico is an unincorporated territorial possession of the United States acquired in 1898 following the Spanish–American War, making it "the oldest colony in the modern world".

[24] Puerto Rico became an unincorporated, organized territory of the US through a series of judicial decisions by the Supreme Court of the United States, collectively known as "The Insular Cases" and the enactment of several statutes by Congress.

[27] In 1952, voters in Puerto Rico approved a new constitution proposed by Governor Luis Muñoz Marin after increased pressure locally along with internationally to decolonize the island; this led to the territory being designated as a commonwealth.

[28] This new title of "commonwealth" did not change how Puerto Rico was related to the United States, allowing Congress to continue holding power over it as an unincorporated territory.

[32] Whether Puerto Rico is given statehood or simply apportioned members of Congress as a Commonwealth or territory, this will have an impact on the make-up of the House.

As the Reapportionment Act of 1929 mandates the House be capped at 435 members, Puerto Rico would end up with Representatives that would otherwise have been apportioned to other states.

This was short lived, since the following year (April 2, 1900) Congress enacted the Foraker Act, which established a civil government and free trade between Puerto Rico and the USA.

[36][37] A referendum in December 1998 offered voters four political status options: statehood, independence, free association, and territorial commonwealth, plus "none of the above."

[44] This was followed by a hearing at the Senate Energy and Natural Resources Committee on Puerto Rico's status on August 1, 2013,[45] and (in 2014) resolutions introduced in both houses of the United States Congress (H.R.

[52] The November 2020 referendum was the first to ask voters a simple yes-or-no question: "Should Puerto Rico be admitted immediately into the Union as a State?".

[54] Although the two referendums (November 2012 and June 2017) also had ostensibly pro-statehood outcomes, The New York Times described them as "marred, with ballot language phrased to favor the party in office".

[57] The bill was introduced to U.S. Congress by Jenniffer González Colón, and had 34 co-sponsors; it would have mandated PR becoming a state of the Union by start of 2021.

[62] On May 16, 2020, Governor Wanda Vázquez Garced announced that a referendum on Puerto Rico's statehood would be held in November of that year.

[63] For the first time in the territory's history, only one direct question was asked: "Should Puerto Rico be admitted immediately into the Union as a State?

The announcement came amid growing disillusionment with Puerto Rico's territorial status due to the lack of access to federal funds for recent natural disasters, such as Hurricane Maria and the COVID-19 pandemic.

It would have instituted a binding referendum that would allow Puerto Ricans to vote on the future status of the island, that Congress would have to obey.

The executive order followed the U.S. House of Representatives' 2022 approval of a bill to help Puerto Rico move toward a change in territorial status.

[102] McConnell stepped down from Leader at the end of 2024, and Senator John Thune took his place, pledging to support Trump policies.

I believe the people of Puerto Rico deserve a process of status self-determination that gives them a fair and unambiguous choice on this matter.

"[105][106] In 2018, as president, Trump stated his opposition at that time to statehood, saying that he would refuse to allow it if any serving Puerto Rico politicians who criticized him, such as the Mayor of San Juan (the capital city), remained in office.

[107] There was media speculation that racist jokes about Puerto Rico and Latino voters, made by roast comedian[108] Tony Hinchcliffe at a Donald Trump presidential election rally in New York's Madison Square Garden in October 2024,[109] could have pushed Puerto Rico's population to vote for statehood in its 2024 Status Referendum, on November 5.

[110] The comedian has a long history of making racist jokes for comedic roast, and was defended by Jon Stewart though the satirical nature of his further commentary is harder to decipher.

[113] In November 2024, Trump picked Florida Senator Marco Rubio to be Secretary of State, someone who had previously endorsed resolutions for Puerto Rico and pushed for increased tax credits for low-income families there.

[115][116][117][118][119][120][121][excessive citations] They also attempted to persuade the members of Congress to initiate a process to change Puerto Rico's political status.

[122] The campaign was supported by former U.S. representative José Enrique Serrano and former Resident Commissioner of Puerto Rico (now Governor) Pedro Pierluisi.

[123] Groups involved included Alianza Pro Libre Asociación Soberana (ALAS), Boricua Ahora Es, Igualdad Futuro Seguro, Renacer Ideológico Estadista (RIE), Proyecto Estrella, Young Democrats of America, and Young Republican Federation of Puerto Rico.