AHC: Independent Puerto Rico

With a POD after the US annexation of the island, make Puerto Rico independent. This cannot involve nuclear war, natural disasters or the collapse of the US. Under these conditions, can Boricuas be independent?
 
Some movement has to fill the streets and be able to make the country ungovernable if the federal government doesn't compromise. A civil conflict or uprising that garners a big death toll or is dragged on long enough could lead to independence if the US is embarrassed enough.

The only way for this to happen is like the collapse of Jim Crow: Puerto Rican civil society has to demand it, either from the ballot box or the streets, and enough in Washington have to agree to it. Any attempt at independence by military means would end in defeat, because the island is too small for a guerrilla force to be a real threat to the US military, and outside support would be impossible. So success of any of the OTL attempts to start armed movements is ASB, even if greatly increasing their popularity and strength isn't.

What would push Puerto Ricans that far? The fact that OTL's events of the past couple years haven't caused serious anti-government/anti-US feelings hints that it's probably not going to happen, at least by the 21st century. But history has plenty of missed opportunities, and maybe there was some point in the 20th century where had the right organization or leadership arose, it could have built on that moment and gone on to sweep Puerto Rican political life with a platform of independence.

There is another possibility I see. If the status quo became so intolerable that the movement for statehood gained momentum and was frustrated by politicians in Washington not wanting to give those electoral votes to the other party, then that could turn into a revival of the independence idea.
 
I think there is a chance if the US decided to never give the Puerto Rican’s US citizenship. Keep as a real colony (it still is a colony today but the citizenship makes other world powers turn a blind eye).

Without that post-WW2 their will be more pressure from Europe for America to get rid of its colonies if America is advocating for the independence of theirs.
 
Well, there's always making the Partido Nacionalista de Puerto Rico, with or without Pedro Albizú Campos (or something like the Party), become to the island what the Indian Nationalist Congress was for the Raj. If you bring the Nationalists into political power early enough - combined with nonviolent civil resistance similar to Gandhi's satyagraha (leading to reactions on the Mainland similar to what happened when the US tried to crack down on the insurgency in the Philippines, which was basically total outrage) - that would make the difference. It would basically be the end of the Raj on speed, combined with the wider Latin American historical context due to dissatisfaction with Cometan positivism (which, although Washington did not realize it, was basically what their colonial rule was) leading people in the region to seek alternatives, and with Puerto Rico in particular feeding on dissatisfaction with being granted American citizenship since it was seen as feeding the conscription pool for the US Armed Forces for WW1. In such a context, the Nationalists could feed on the anti-conscription feeling on the Island and use it for trying to achieve independence by peaceful means. Then, once our FDR equivalent comes on the stage, seeing as the 1930s was when the US pulled back from occupying various Latin American countries, at some point Puerto Rico too would be swept up in this wave - even if it means something similar to what would soon exist for the Philippines (which was basically the Commonwealth model as originally intended, as a transitional stage to independence), at first.
 
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