One of the most surprising stories of the Olympics, which end on Sunday, was the unseeded Monica Puig's improbable march to the gold medal in women's singles tennis. Puig's win captured Puerto Rico's first-ever gold medal in the Olympics, and set off massive celebrations across the island. It was a big-ass deal.

Hold up, you might be thinking. Why does Puerto Rico have its own Olympic delegation? Aren't Puerto Ricans considered American citizens? The answers to those questions are layered and fascinating, as I learned when I sat down to talk with Antonio Sotomayor, a professor at the University of Illinois-Urbana. Sotomayor wrote the book The Sovereign Colony: Olympic Sport, National Identity, and International Politics in Puerto Rico. Sotomayor told me that the very, very complicated relationship between the U.S. mainland and the island territory with its long colonial history has always been the not-quite-subtext of Puerto Rico's international athletic endeavors. We talked about that history, the political importance of Puig's win, and Puerto Rico's shocking demolition of the U.S. powerhouse men's basketball team in 2004. An edited and condensed version of our conversation is below.

Gene Demby: So why does Puerto Rico — which is not a sovereign nation — even have an Olympic delegation? How did that come to be?

Antonio Sotomayor: That's, of course, a complicated topic. Puerto Rico has a sovereign Olympic delegation without political sovereignty, which goes back to the early 20th century. There are different reasons: diplomatic reasons involving the relationship between the U.S. and Latin America; the internal development of the Olympic movement and the Olympic Games needing delegations to participate in the games; and solidarity between Central American and Caribbean countries.

You have to move away from looking just at the Olympic Games — you have to look at the whole set of regional games that are part of the Olympic Movement. In the case of Puerto Rico, particularly, there's the Central American and Caribbean Games, one of those early regional games, which started in 1926. The first of those games were only held in Guatemala, Mexico and Cuba...

GD: Because they were the places that had the infrastructure for big sporting events.

AS: Right. This was brand new, and at a time when the Olympic movement was on exploratory, unstable ground or localized in Europe, and they were trying to expand. The organizers in Havana, Cuba, made an effort to go in ships to really invite delegations to participate.

GD: Was that a hard sell?

AS: Not really, because you had the growth of sport as a medium physical education, as a new medium of cultural progress and modernity, a whole set of ideas that sport symbolized the new 20th century. So it was easy to convince these countries to participate in this festival that was for international goodwill among countries.

And so in 1930, you have these countries agreeing to participate in the second edition of the [Central American and Caribbean Games, of CAC] and Puerto Rico received an invitation from the U.S. ambassador in Havana, Cuba, who said, well, the U.S. has a delegation in Puerto Rico, so we'll try to send that delegation. But it was for strategic purposes: in the 1930s, you have a shift in U.S. approach in the region from gunboat diplomacy to a "good neighbor policy."

GD: It's the "soft power" approach.

AS: Right. So they said: they're U.S. citizens, so I guess we can send them. So Puerto Rico attended the games, but carrying the U.S. flag.

GD: So there was this imposition of the literal banner of the United States on the Puerto Rican delegation.

AS: Not necessarily an imposition. Because for Puerto Ricans, having U.S. citizenship and an association with the U.S., like many Puerto Ricans today, was something they embraced willingly. They wanted to be recognized as Americans. Many Puerto Rican leaders were saying, "We will be representing the U.S at these games, but we will do it as Puerto Ricans."

And you have in the Olympic movement in general, but in Puerto Rico, as well, a movement of all these different ideologies and purposes. There were people who were very much in favor of the association with the U.S. and representing both countries. But you also had Puerto Rican nationalists. The actual flag-bearer for those [CAC] Games was a man named Juan Juarbe Juarbe. He was mainly track and field — and also a very good basketball player but [Puerto Rico] didn't have a basketball team at that time. But he was a Puerto Rican nationalist, and he carried the U.S. flag in the opening ceremonies.

So he came back to Puerto Rico, and he was recruited by Pedro Albizu Campos, the 20th-century liberation fighter — some people call him a martyr — an intellectual and fighter for Puerto Rican independence. Juan Juarbe Juarbe then became the nationalist party's foreign relations secretary and then traveled around the world claiming the right of Puerto Rico's independence.

So during the 1930s, you have that negotiation going on. And then in the 1935 [CAC] Games in El Salvador, the Puerto Ricans actually pulled out a Puerto Rican flag — which was not used back then as an official flag in Puerto Rico except by nationalists — and they used it in the opening procession as an act of nationalism. The purpose that the U.S. had for having Puerto Rico participate in the Central American Games, of having Puerto Rico at those games for diplomatic reasons, sometimes backfired. The U.S. strategy in sending was always [confronted by] the Puerto Rican impetus to show they were a different nation to some extent.

[Sotomayor said that after World War II, Europe's diminished imperials powers had a more tenuous grasp on their colonies. Caribbean countries that were moving toward independence — like Jamaica, notably — began participating in the 1948 Olympic Games as their own delegations.]

AS: The U.S. didn't want Puerto Ricans to participate in the 1948 Olympic Games as their own delegation. They came out of the world war strong, so they could just hold on tight. They wanted the Puerto Rican delegation to participate with the U.S. delegation, like Alaska and Hawaii did, in the 1948 games. But Avery Brundage, who was the head of U.S. Olympic Committee, understood the political context: how could the U.S. deny Puerto Ricans in the Olympic Games in 1948 when they just finished fighting for democracy, freedom and imperialism? And they were behaving like that empire, that was his arguments. He told them, we had to cancel the 1940 and 1944 Olympic Games [because of the war], we need more countries to participate. And because Jamaica and Puerto Rico had participated in the Central American Games, he said that they should let them to help the movement would be legitimized.

GD: So if this were happening today, Puerto Rico probably wouldn't exist as a discrete Olympic venture.

AS: Right. The Olympic movement doesn't need it. If Puerto Rico were to become a U.S. state, some people think it would keep its Olympic sovereignty. But the Olympic committee has said... no, if you elect to become part of a bigger country, we assume your Olympic committee would disappear.

GD: But those aren't necessarily the same impulses! Just because people make a political decision to align themselves with the United States as a state, in this case, doesn't mean they want to dissolve their Olympic presence.

AS: Many U.S. statehooders — that's what we call them — want to keep a Puerto Rican identity and follow the dream of the Founding Fathers that this was a union of sovereign states. And they want to carry that sentiment into possible statehood, including having an Olympic delegation. It also depends on how the U.S. admits this new territory and this stipulations. They could say, "we have this idea of one nation, one Olympic committee."

GD: Do Puerto Rican athletes have to think pragmatically about which team to play for in the Olympics? I'm thinking of Monica Puig. If she was on the U.S. team, she'd have to get around the Williams sisters — there's this logjam at the top of U.S. tennis. Is that a thing that people are navigating a lot?

AS: With all the sporting infrastructure, Recently, there was Gigi Fernandes, another tennis player, and she was pretty good. And then she switched her Olympic citizenship and played for the U.S. From what I read recently, she thought she had better infrastructure and opportunities. In another case, Carmelo Anthony [the New York Knicks and USA Basketball star] could play for Puerto Rico, and he identifies as Puerto Rican. In that team scenario, he has a better chance of winning a medal.

I'm working on a paper trying to understand Puerto Rico's political nationalists and their views on Puerto Rican Olympic sovereignty and national identity. There's a sense of patriotism in Puerto Rico that has to be taken into into consideration. Many athletes, that sense is really strong, and if they could participate, many of them would play for Puerto Rico, even if they could play for the U.S. But then again, there are very few cases. And Monica, got her gold medal in a very important sport...

GD: Why is tennis so particularly important?

AS: It's very popular, it's one of the sports that gets a good audience, at least in the developed North Atlantic — the U.S. and Europe. And to win a gold medal in a sport that's highly associated with the English aristocracy...[players] have to dress in white at Wimbledon. And for someone from this small island to win in this protected space ... protected literally, like, don't speak during the serve, don't say anything, if you want to scream and shout, go to a [soccer] game! When you put it into the context of the struggle of this island that has been living under a colonial relationship for more than 500 years, the only cultural medium in which they are recognized by the international community as a sovereign nation, any medal is important. But the gold, visually, puts you at the top of the podium, and you play the anthem — it's the only anthem played. On multiple levels, winning a gold in that sport is extraordinary, and Puerto Ricans understand it.

I think Monica Puig said in multiple interviews, winning the WTA tournament is my job. But putting on the Puerto Rican jersey is special, is for the glory of Puerto Rico.

GD: Right. Puig "feels the shirt."

AS: And this is why the politics and the Olympic movement cannot be separated. Because you have that victory for Monica Puig, you have a whole nation united. For two days, Saturday and Sunday, there were no murders in a place that averages two or three murders a day. The superintendent came out and said, "We didn't have any murders and I think it's because of Monica Puig's victory."

My mother, who is still on the island, said there was a priest who stopped Mass to watch the match and put his microphone to his cellphone and everyone listened and cheered. There was a whole party. And then he said, Okay, now let's resume Mass. [laughs]

GD: [laughs] That's amazing.

AS: It's incredible. And that all happened in celebration of the Puerto Rican nation. Monica Puig's victory and a victory of this imagined community called Puerto Ricans. For the pro-statehood movement, who want to assimilate into the U.S. culture, it's a thing they have to deal with. In and of itself, that victory, that nationalistic feeling is an impediment to Puerto Rico's assimilation. Even if you say, let's separate it from politics, the existence of Puerto Rico's Olympic committee is a political brick wall for the pro-statehood movement.

GD: Before I go, can we talk about that 2004 men's basketball game? [In the 2004 Olympics, Puerto Rico shocked the basketball world by beating the American team, comprised of NBA stars, by 19 points in the group stages. — Ed.] It's still so ridiculous. You have a team with LeBron James and Tim Duncan and Allen Iverson...

GD and AS: [in unison] Dwyane Wade...

AS: Big names. The biggest.

GD: ...and they get stomped by Puerto Rico.

AS: Yeah. Puerto Rico has had a good basketball program since the 1950s. We've had very good basketball players. To me, the decade of the 1990s, was the best decade of Puerto Rican basketball, perhaps because it was my era...

GD: Did you play?

AS: I did but I was not good at all. But I loved it. I loved it.

GD: Man. Same here.

AS: And then you have that generation of the 1990s player, that was starting to retire. For some reason, that game, they gave them their best, and the U.S. with their big names, had grown used to just rolling over teams internationally. And the Puerto Ricans got the best of them and just beat them. For Puerto Rico, it was very special — very similar to what we're seeing now with Monica Puig. Back then, the U.S. was the Dream Team ... they had been beating other countries by 30 or 40 — good for them, but horrible for the rest of the world. And then you have this small island having to get enough players to beat this dream team — they ended up winning by 19 but they were winning by 24 at different points.

GD: They were way up.

AS: For Puerto Ricans, that whole historical context of an island that's been under colonial rule, without political voice or face to the world, beating the most popular team in the world in one of the most popular sports, was extraordinary. And it meant a lot — not only because of the sport, but because they did it to the U.S.

GD: Right.

AS: The metropole. The country that has control over this other island. The symbolism is very strong. And to contextualize it, it becomes more than just winning a game. For many, beating the U.S. at that game at the particular moment in time could have been better than winning a medal. Sure, they would have taken the gold — they would have celebrated! But the historical meaning, for the nation, was just extraordinary.

GD: I remember seeing — well, not the highlights, because NBC didn't share the video with other networks — but the photo stills from that game, and listening to the commentary. And I could not wrap my mind around the fact that it happened. Puerto Rico is an island of 3 million people...

AS: It's going down, definitely. We had 4 million people but now we're down to 3.4 over the last decade. Half a million at least have fled the island.

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