Today President Obama is making the first official Presidential visit to the U.S. territory of Puerto Rico since John F. Kennedy in 1961.

The first thing President Obama might discover during his visit is that if he moved to Puerto Rico, he would no longer be able to vote for himself.  Although Puerto Rico is part of the United States and home to almost 4 million U.S. citizens — larger than 22 states — none of them, not even the thousands who serve in the U.S. Armed Forces, can vote for the Commander-in-Chief.  Like the residents of Obama’s current home city of D.C., they are also denied voting representation in both the House and Senate.

But government by consent is not the only Founding principle absent in Puerto Rico. When President Obama’s plane touches down on the Island of Enchantment, he would be interested to learn that while federal laws “follow the flag” to Puerto Rico, the Constitution and its principle of a government of limited and enumerated powers do not.

The reason is a series of controversial and sharply divided Supreme Court decisions known as the Insular Cases that were decided shortly after the United States acquired overseas territories following the 1898 Spanish American War.  In order to accommodate America’s imperial agenda, the Supreme Court in the Insular Cases turned its prior precedent and the text and history of the Constitution on their head to establish a doctrine of “separate and unequal” constitutional treatment for overseas U.S. territories.

While the continuing vitality of the Insular Cases has been in question for over fifty years, they remain a part of our constitutional law.  As the Court recently recognized in Boumediene v. Bush, which dealt with the extra-territorial application of the Constitution in Guantanamo Bay, Cuba, the Insular Cases still stand for the proposition that the Constitution applies “only in part in unincorporated Territories” like Puerto Rico while it applies “in full in incorporated Territories surely destined for statehood.”  This distinction between “incorporated” and “unincorporated” U.S. territories, a creation of the Supreme Court that has no apparent basis in the text or history of the Constitution, places the constitutional rights of almost 4.5 million Americans in the hands of Congress . . . where they lack any voting representation.

But even as the Court in Boumediene found the analytical framework of the Insular Cases useful in determining that the Constitution’s Suspension Clause applies in Guantanamo, it went out of its way to question the continuing validity of the Insular Cases in modern-day U.S. territories.  Writing for a five-Justice majority (the dissent didn’t reach these issues), Justice Anthony Kennedy suggested that the Insular Cases should be limited to “the particular historical context in which they were decided,” and that “[i]t may well be that the ties between the United States” and its overseas U.S. territories have “strengthen[ed] in ways that are of constitutional significance.”

The Court’s reasoning in Boumediene—that “[t]he Constitution grants Congress and the President the power to acquire, dispose of, and govern territory, not the power to decide when and where its terms apply”—is hard to square  with the Insular Cases’ territorial incorporation doctrine, which holds that Congress has the power to determine whether a U.S. territory is “incorporated,” and, if not, whether certain constitutional rights apply.  In fact, the Court in Boumediene expressly rejected the notion that the “political branches have the power to switch the Constitution on or off at will,” stating in unequivocal terms, “Our basic charter cannot be contracted away like this.”

President Obama would get an earful about the Insular Cases while he is in Puerto Rico if he stopped by the chambers of some of the federal judges who serve there.  Judge Juan Torruella, the former Chief Judge of the First Circuit who sits in Puerto Rico, recently authored a dissenting opinion where he cited to Boumediene for the proposition that “changed conditions have long undermined the foundations of the[] judge-made rules [set forth in the Insular Cases], which were established in a by-gone era in consonance with the distorted views of that epoch.” Criticizing continued application of the Insular Cases, he explained that “the continued enforcement of these rules by the courts is today an outdated anachronism, to say the least.”

In Torruella’s view, “[a]llowing these antiquated rules to remain in place, long after the unequal treatment of American citizens has become constitutionally, morally and culturally unacceptable in the rest of our Nation . . . is an intolerable state of affairs which cannot be excused by hiding behind any theory of law.”  Quoting directly from Justice John Marshall Harlan’s powerful dissent in Downes v. Bidwell, the most famous of the Insular Cases, Torruella emphasized that “[t]he idea that this country may acquire territories anywhere upon the earth, by conquest or treaty, and hold them as mere colonies or provinces,-the people inhabiting them to enjoy only such rights as Congress chooses to accord to them,-is wholly inconsistent with the spirit and genius, as well as with the words, of the Constitution.”

Judge Gustavo Gelpí, a U.S. District Court judge for the District of Puerto Rico, would also have a thing or two to say.  In an essay that recently appeared in The Federal Lawyer, Judge Gelpí observed that the Court that decided the Insular Cases is the same that decided Plessy v. Ferguson.  Moreover, he cautioned that the constitutional status of Puerto Rico is not merely an academic question, arguing that “even today the constitutionally denigrating ripple effects of the Insular Cases doctrine continue to foster a separate and unequal treatment to U.S. citizens therein.”  Gelpí echoes Torruella that post-Boumediene “[t]he time has very much belatedly come for the U.S. Supreme Court to revisit and remedy the anachronistic and denigrating judicial predicament that today nearly five million United States citizens residing in Puerto Rico and other U.S. territories have sustained for more than 110 years.”

President Obama’s trip to Puerto Rico falls on the heels of a Presidential Task Force Report supporting a process that ultimately will determine the future of Puerto Rico’s relationship with the United States.  Where the Insular Cases fit into the future of that relationship remains to be seen and, as Boumediene indicates, is a very live issue to be decided by the Supreme Court.