“The United States is always demanding democracy in other parts of the world,” Rosselló told the Miami Herald, “but it seems to me it doesn’t have the moral standing to demand democracy in Venezuela or Cuba if it won’t extend [democracy] to 3.5 million of its own citizens.”

. . . For Rosselló, the debt crisis and the island’s political status are inextricably linked: “Puerto Rico’s colonial situation is what has provoked this crisis. If we compare ourselves with the other 50 states, the fundamental difference is our lack of rights, our lack of participation, and our lack of resources to move our jurisdiction forward,” he said. “Our colonial condition creates a situation of incredible inequality.”

The island-wide vote … seeks to resolve the “colonial condition” once and for all. It will offer two stark choices: statehood or independence. If the latter wins, a second vote will be held letting people decide between full independence or keeping the current commonwealth, or “associated free state,” status.

The situation is quite similar to that of 2012, but its origins stretch back to the turn-of-the-century US acquisition of a colonial empire after the Spanish-American War.

As I’ve explained for the History News Network:

So how did Puerto Rico’s ambiguous political status come about?

Put simply, in the wake of the Spanish-American War, Puerto Rico became an American colonial dependency, but one piece of a new American empire, acquired in what historian Robert Osgood once provocatively described as “a fit of absentmindedness.”

Republican President William McKinley famously led the nation to war against the Spanish Empire in 1898, caught up in the jingoism that gripped the American public following the mysterious sinking of the USS Maine in the Spanish-held harbor of Havana, Cuba.

Spanish defeat led to various American colonial acquisitions, among them de facto U.S. control of Cuba and de jure control of the Philippines and Puerto Rico.

The United States was left with a quandary. What was the United States to do with its newfound empire? Should the United States incorporate the new colonies within the American union as equals, as if they were American states? Or should the United States treat these non-contiguous territories differently, as subordinate colonies?

Fascinatingly, the future of American imperial policy rested upon how it first treated Puerto Rico.

The McKinley administration’s actions toward Puerto Rico in 1900 therefore laid the groundwork for subsequent ad hoc American imperial policies toward its other colonial acquisitions. As the pro-imperial American Economist described in 1900: “No question that has been before Congress during … any recent session has caused greater interest among the leaders of both parties” than how the United States would deal with Puerto Rico.

McKinley had at first favored a liberal trade policy, to fiscally treat Puerto Rico “like Oklahoma and Alaska.” But the Republican administration quickly reversed this decision upon the realization that such a precedent would play out throughout the new colonies, including in Cuba and the Philippines.

A combination of economic and xenophobic fears over direct competition with Cuban sugar growers, “shrewd, cheap” Filipino labor, and a potential deluge of exports and Asian immigration to the United States curtailed this more liberal economic approach toward Puerto Rico. As a spokesman for the McKinley Administration put it: “He don’t want any legislation for Puerto Rico that will keep us from legislating for Manila.”

The McKinley administration therefore ignored various American and Puerto Rican calls for equal treatment and instead instituted a protective tariff policy upon Puerto Rican goods imported into the United States.

Impotent American anti-imperialists promptly condemned this decision to treat Puerto Rico “in a manner different from … an organized Territory of the United States,” calling it “the entering wedge of ‘imperialism.’”

Puerto Rico and the Insular Cases

The U.S. Supreme Court’s subsequent May 27, 1901 decision thereafter legalized the burgeoning American Empire.

The Supreme Court’s legal decision in Downes v. Bidwell (1901) became the first of the now-infamous Insular Cases. By allowing McKinley and Congress to implement protective tariffs upon Puerto Rican goods rather than granting them free access to the American market, the decision “decreed” that the Constitution “does not follow the flag.”

In The “Insular Cases” and the Emergence of American Empire, Bartholomew Sparrow has reminded us how the Supreme Court’s decisions had long-lasting ramifications for American imperialism. As late as 1922, in Balzac v. Porto Rico, the Supreme Court held that Puerto Ricans, while U.S. citizens, were not guaranteed the rights of the U.S. Constitution.

“The United States is in clear violation of not only the Constitution but also the treaties that we have entered into which are of course the law of the land,” Judge Juan Torruella, the first Puerto Rican to be appointed to a federal appellate court, has reproachfully observed.

If the Insular Cases still aren’t ringing any bells, they should: they recently played a crucial role in dealing with detainees held in U.S. military detention in Guantanamo Bay after September 11; and to this day they are still used to deny Puerto Ricans constitutional rights guaranteed to the rest of American citizens — which brings us back to the topic at hand.

Twenty-First-Century Shadows of the American Empire

In fits and starts in the decades since it became incorporated within the American Empire, Puerto Rico has admittedly gained a modicum of autonomy over local affairs: but not over foreign policy, let alone the ability to vote in federal elections.

And so Puerto Rico has remained a phantom limb of the American body politic — not quite an American state, not quite a U.S. colony, and not quite a sovereign nation. “The kind of imperial colonial status created at the turn of the century has never been eradicated,” notes Roger Smith, a professor of political science at the University of Pennsylvania.

And, while the recent and remarkable Puerto Rican election results appear to represent a majority vote in favor of statehood, sizeable hurdles yet remain.

The biggest impediment will be the U.S. Congress, which now gets to determine Puerto Rico’s fate.

While President Obama states he is “committed … that the question of political status is a matter of self-determination for the people of Puerto Rico,” it looks very unlikely that the Republican-controlled House of Representatives will agree.

Republican politicians have long opposed such a development. You see, Puerto Ricans living in the United States overwhelmingly vote Democratic, and the political parties in Puerto Rico invariably are “one shade of Democrat or another,” John Hudak of the Brookings Institute points out.

Much like 2012, the Republicans once again control the House, added to which the GOP now controls the Senate and the executive, too. And so in June, should a majority of Puerto Rican voters again vote in favor of statehood, Puerto Rican democracy will once again encounter Republican imperial opponents in Washington who will try to make sure that Puerto Rico maintains its quasi-colonial status.

Nevertheless, some Puerto Rican statehood supporters remain hopeful that Donald Trump will support the referendum results, based on statements he made on the presidential campaign trail. And there is some precedent – Trump has came out in strong support of the UK’s 2016 non-binding referendum in which a slim majority voted to leave the EU.