On Sunday, President Obama will begin his historic visit to Cuba. He will be the first president since Calvin Coolidge to visit the island, and his mission is a prime manifestation of what some people—not me, necessarily—might call the “Obama Doctrine.” Obama has been remarkably consistent over the years in questioning why adversaries of the United States have remained adversaries, and in Cuba, at least, he has an answer: They don’t have to be adversaries, at least not all of them. (The chance of an Obama victory lap in Tehran appears at the moment to be vanishingly small, despite the nuclear agreement.)

Over the years, Obama has been criticized steadily for “apologizing” on behalf of the United States for its various alleged misdeeds in other countries. As he told me in one of my recent interviews with him, “We have history. We have history in Iran, we have history in Indonesia and Central America. So we have to be mindful of our history when we start talking about intervening, and understand the source of other people’s suspicions.”

Obama clearly believes that acknowledging the complicated history between the United States and certain developing-world countries is a prerequisite for better relations (the jury is out, I believe, on whether this is, generally speaking, an effective tactic, or more just a trolling of the American right). Though he did not name Cuba in this list of countries that have been wronged by past American policy, it is entirely plausible he considers at least some of that country’s claims legitimate, such as those regarding U.S. support for the Batista regime, which was overthrown by Fidel Castro and his guerrilla army, and for the Bay of Pigs invasion and other regime-changing schemes.

I mention this because in a recent conversation, Ben Rhodes, Obama’s deputy national-security adviser, foreign-policy amanuensis, and secret Cuba envoy, mentioned that it was Obama’s respectful treatment of Raul Castro, Fidel’s brother and the current president, at the December, 2013 funeral of Nelson Mandela, that may have helped the then-nascent, and then-unpromising, negotiations with Cuba turn a corner. “We had been in negotiations with the Cubans secretly for about six months at that time and hadn’t really gotten anywhere,” Rhodes said, explaining that Cuban suspicions of American intentions were almost overwhelming. “We were mainly talking about their desire to recover several Cuban prisoners in the United States and Florida—the remaining members of the Cuban Five—and our desire to return [USAID contractor] Alan Gross to the United States, but we wanted a bigger package. We wanted to use the exchange of some prisoners as an entry point to changing the relationship.”

Mandela’s funeral provided the White House with the opportunity to change the tenor of the talks. “The president was going to the funeral of Nelson Mandela—his personal hero—and I remember on the plane to South Africa I raised with him—we had a list of the leaders who were going to be up on the dais where he’d be speaking—and one was Raul Castro, and I said, ‘Look, inevitably it is going to come up as to whether or not you shake his hand.’”

Obama’s response was not necessarily the response of a typical American president. According to Rhodes, Obama said, “‘Look, the Cubans, given their history with Mandela, with the ANC, they have a place at this event, and I’m not going to, essentially, cause an uncomfortable situation for the Mandela family, for the South African people, by snubbing the president of Cuba who has a right to be on that dais.’” The Cubans were early and ardent supporters of Mandela’s African National Congress party, and were also deeply engaged militarily across southern Africa. I asked Rhodes what “right” he was referring to. He said, “Well, look, whatever you think of the Cuban government, they supported the anti-apartheid movement; they fought side-by-side with the ANC; the Castros had a relationship with Mandela. And this is the president’s hero and he doesn’t want to cause an incident at his memorial service by carrying forward this dispute between the United States and Cuba, so he shook Raul Castro’s hand.”

Castro, Rhodes said, was a bit surprised, and perhaps somewhat moved. “What was interesting was, in our subsequent meetings with the Cubans, the atmosphere changed a bit, and the first thing they said to me in the next meeting was how much President Castro appreciated that President Obama had done that, and it kind of established a tone where they understood they were dealing with a different American president—one who is willing to leave the history in the past and actually try to get something done.”

My conversation with Rhodes about Cuba (part of which you can watch below; the full version is here) continues below. I’ve edited the transcript for concision and clarity.


Jeffrey Goldberg: You know, the small irony here is that the president, President Obama, is known as a cool, transactional kind of foreign-policy president, but here you’re saying there was an actual kind of personal-connection moment.

Ben Rhodes: Well, what’s interesting is that the emotion was on the Cuban side. You know, the Cubans have so much built-up, pent-up history with the United States, and in that one small gesture I think President Obama indicated that we can have discussions based upon a sense of mutual respect, and that there is a place for Cuba at an event like that—the memorial service for Mandela—and again, that kind of opened up the space in our negotiations where they felt like they were dealing with a different American president.

Goldberg: Since we opened the door here, the president has an unusual understanding—unusual compared to previous presidents, let’s say—of American culpability in certain parts of the world—Indonesia he’s brought up with me, obviously, Iran and Mossadegh. It sounds as if you’re saying that he almost endorses the help Cuba gave to the ANC in the ’70s and ’80s. Is that fair, or am I taking that too far?

Rhodes: Well, I think there’s complexity to it. He doesn’t endorse the political system of Cuba or the human-rights practices of the Castro government, but at the same time, he can see shades of gray in history. We had used the black-and-white version of history to justify Cuba policy that didn’t make much sense; that was far past its expiration date. I think that he had enough of an understanding of history to know that whatever we think about the Cuban government’s political system and human-rights practices that, in fact, when it came to the anti-apartheid movement, they had a place on that dais at Nelson Mandela’s memorial service, and he was not going to, essentially, disrespect the legacy of Nelson Mandela by carrying forward that history and snubbing the Cuban president because of our bilateral relationship.

Goldberg: In broader terms, give me the theory of Obama’s case on Cuba. I wrote that he has an unusual willingness to question the assumptions that go into bilateral relations with various countries, and the assumption that he was questioning in the Cuba relationship was, “Why does it have to be this way?” But what’s the larger theory of the case?

Rhodes: I think there are three things. One is, America sometimes makes itself a prisoner of our own history. We have a very complicated history with Cuba. We’ve had significant historical differences with Cuba. But that alone can’t be the rationale for continuing a policy that’s not working. That leads to the second point, which is, he has a deeply pragmatic streak. If you just looked at our Cuba policy in isolation coming into office—it’s not working. The embargo is not working—it’s not doing anything except punishing the Cuban people. The Castro government is still firmly entrenched in power, and the Cuban people are suffering. And the third point is, you take those two facts and you say, “This is holding us back in the hemisphere and in the world, because of our history, because of our unwillingness to look at a failed policy and change course, we essentially have an anchor on American standing in Latin America and, in some cases, in the rest of the world. And why not cut that loose and open up the door to greater opportunities?”

Goldberg: I want to come back to that, but one of the things that you didn't mention was a notion that by opening Cuba, you’ll change Cuba, particularly on human-rights issues and democratization issues. Is that not a priority of the president?

Rhodes: It’s absolutely a priority. There are two openings here. One is to Cuba, and we believe that the Cuban people are suffering under the embargo—that the Cuban government is very comfortable in a situation where we’re just seeking to isolate them, pressure them, support a number of actors inside of Cuba but not reach out to the whole Cuban people. By opening up travel, by opening up commerce, you’re going to empower the Cuban people. They’re going to get more resources; they're going to have more interconnectivity to the rest of the world. This over time has a greater chance of improving the human-rights circumstances in Cuba than isolation and pressure.

The second point is about Latin America. When we came into office, the wind was at the back of Hugo Chavez and Evo Morales and the anti-American forces, the ALBA movement in Latin America, in part because we played to type—we played exactly into the type that they wanted, which is the Americans coming and telling people who should run their countries, the Americans are throwing their weight around in the region in ways that fed this ideological dispute. By removing ourselves from that conversation, we remove a rationale for those anti-American leaders. And in fact you’ve seen just in the last several months elections in Argentina, in which the anti-American president Cristina Kirchner was replaced by a very pro-American president, President [Mauricio] Macri, who we’ll be visiting after Cuba, and you’ve seen Evo Morales lose a referendum in Bolivia. I’m not saying there’s a direct causal effect to our policies, but it is indisputable that we have removed ourselves essentially as a justifying force for those leaders in the region who have a politics that is rooted in anti-Americanism.

Goldberg: It’s an issue of great controversy, shortly before this historic first trip by the president to Cuba, about whether he’s even going to see human-rights dissidents, political dissidents. Can you give us a little bit of where the thinking is there, and would you be satisfied to go to Cuba and not meet political dissidents? Are you strengthening inadvertently the hand of a single-party state and its repressive system?

Rhodes: So first of all, we will see dissidents. We’ve made clear to the Cuban government that we see who we want to see in other countries.

Goldberg: There's been pushback from the Cubans, though. Is that fair?

Rhodes: Not on the president, no. I think they know, because we laid down the marker at the very beginning that we’d be seeing dissidents on this trip. But the second, and more important point is, we utterly reject this notion that there’s only one way to promote democracy and human rights. There are a group of people, I think, in the United States who say, “The only way to demonstrate that you care about human rights in Cuba is to criticize the regime, isolate the regime, and only try to engage with dissidents.” We don’t think that works. We care just as much about human rights and democracy as those people, but the fact of the matter is, we don’t think doing something that’s not working is the way to go about promoting democracy and human rights. We think we’re going to be better positioned to do it through engagement. Just one small example is having an embassy. This has been treated as some kind of concession, to have an embassy set up in Cuba. The fact is, having an embassy in Cuba allows us to have more contact with the Cuban people, whether it’s dissidents, civil society, entrepreneurs, and others. So we believe that this is a better way, through engagement, of advancing the things that we care about.

Goldberg: Frame this out in terms of Asia, because the theory applied to Asia doesn’t seem to work so far in the following sense: We have massive business with China, obviously, but China is not a free country by any means. Vietnam is another example of a country that we’ve had very, very good commercial ties and political ties now, but there’s not a lot of evidence to suggest that that exposure to American businesses, American tourists has loosened up the system. What makes you think that Cuba could be any different?

Rhodes: Because the context is entirely different. Asia is thousands of miles away. Cuba is 90 miles from Florida. I’ve talked to Cuban Americans all the time, including Cuban Americans who supported the embargo for many years and who will tell you, whether it’s a Carlos Gutierrez or Mike Fernandez, significant figures in the Republican Party who have said to me, “Look, I supported the embargo. I thought it was the appropriate policy for a long time. But Cuba is going to change and we need to be a part of that change.” And if we’re not engaging Cuba, we won’t be a part of that change. And the fact of the matter is, if you have that level of commerce, that level of travel, that interconnectivity between the United States and Cuba, and between Cuban Americans and Cubans on the island, I think it’s going to be a much greater level of engagement than we would have with a China or a Vietnam that is so far away from the United States, so culturally removed from the United States. We do believe that as this opens up, and as you have greater access to information, greater access to travel, greater access to the international community, to the United States, the Cuban people are going to be in a better position to determine their own future.

Goldberg: It almost sounds as if you’re saying that Cuba will not be able to withstand the weight of American openness on their system, meaning, when you have thousands of Americans staying in Airbnb properties in Cuba and Internet access and Miami television coming in, that the system is inevitably going to change that way. Is that fair to say that the president believes that over time—five, 10, 15 years—we’re going to see a very different Cuba because that weight is going to be pressing down on the country?

Rhodes: Well look, let me begin by saying, we’ve made clear that we’re not in this for regime change. We’re not seeking to impose a new leadership on Cuba. We’re not going to choose who the leaders of Cuba are. That’s for the Cuban people to decide. But the fact of the matter is, if Cuba is opening up, if you have that degree of interconnectivity, if Cubans can access more information, they will be in a much stronger position to make decisions about their own future. They will have much greater control over their own livelihoods if there’s increased commerce, if there’s increase entrepreneurship in Cuba. So yes, we do believe that as this opens up, and as you have greater access to information, greater access to travel, greater access to the international community, to the United States, the Cuban people are going to be in a better position to determine their own future.

Goldberg: Do you believe that the Miami Cubans will come back into play as a powerful force in Havana, and is that something that you want?

Rhodes: Well, what’s interesting is I think there’s been an evolution among many of the Miami Cubans, which, again, I think it used to be kind of viewed through a zero-sum window: Either the Castros are running Cuba or there’s certain people in Miami who are waiting to go back and run Cuba. I think that was kind of the binary view of some in this situation. I think what you’re seeing now is, there’s a recognition in both Cuba and in the Cuban American community, including in Miami, that Cuba is changing. Raul Castro has set in motion a series of reforms that are evolving the economic model; there’s going to be a political transition—Raul Castro said he’s going to leave power; and that there’s an acceptance that this can be evolutionary change—that it need not be the type of regime-change effort that the United States would have supported in the past, but rather if you have Cuban Americans who are getting more engaged in the affairs of the island and the economy of the island, who are rebuilding bridges to their own families and friends on the island, that ultimately that is going to help serve for a more stable evolution of Cuba that is going to improve the lives of the Cuban people and, ultimately, I think, reconcile the Cuban American community with the island.

Goldberg: So this is a third way, you think?

Rhodes: I think it’s a third way, absolutely.

Goldberg: Let me ask you one very specific question on Cuba. It’s specific, but I think it concerns a lot of Americans, which is, it’s the flipside of this—the fear that the inundation of American business, the fear that the flood of money and tourists will actually change Cuba, make it more like the rest of the Caribbean, where you’re going to have in five years McDonald’s in the squares of old Havana. Is that something that you’ve picked up from the Cuban side is of great concern to them? I mean, what are they doing to try and manage that process, and is it actually a care of the administration, or does this administration say, “Great, the more American businesses the better?”

Rhodes: Well, you know, I think first of all there is something unique about Cuba, that is informed by history but also informed by the nature of the place, that has captured the imagination of the American people and the world.

Goldberg: Well it’s been frozen in amber.

Rhodes: Yes. I mean, on a very practical level, I think the Cubans have plans to try to preserve their heritage, to preserve old Havana, to try to develop incrementally when it comes to their tourism sector in a way that doesn’t transform the island into just another tourist destination. So part of that is just going to be how do they manage development. But another piece of this, and this is very important: As we’ve been talking to American companies, and as we’ve been thinking about our own policy changes, we very much want to encourage industries other than just the travel industry to get engaged in Cuba. Our technology and telecommunications companies to help bring advanced technology and access to information to Cuba.

Goldberg: So Alan Gross was just five years too early.

Rhodes: Well, but, and here’s the important thing about Alan Gross, and I think Alan himself would probably subscribe to this view—this is a good example of why what we’re doing doesn't make sense. We used to have a policy where we have an embargo in place, and then we try to bring cell phones into Cuba, and we try to bring printers into Cuba, and give those to dissidents. What’s a more efficient way of promoting access to information—shipping a bunch of cell phones to Cuba, and computers to Cuba, and try and hand them out to people surreptitiously, or just lifting restrictions so that cell-phone technology can go to Cuba, cell phones can go to Cuba? If you want to connect Cuba, lift the embargo. Don’t try to, you know, smuggle some phones down there and hand them out.

Goldberg: Let’s talk foreign-policy theory. My theory of the case—you don’t have to subscribe to it—is that Burma was in some way practice for Cuba—opening up a closed society. So the question is, is what you’re doing in Cuba—do you think it has any relevance to America’s relationship with Iran, which is obviously a whole other category of traditional adversary? Are there lessons that can be applied to that, or is that just Pollyannaish thinking?

Rhodes: Well there’s two things. You know, one is, one commonality between the Iran deal and the Cuba opening is, in the president’s judgment, the approach we were taking wasn’t working—Iran was advancing its nuclear capability, the Cuban regime was firmly in power—and we can test whether another approach works without giving anything up. With respect to the Iranian nuclear deal, we were able to test whether Iran can comply with this deal over an extended period of time, and if they don’t we can re-impose our sanctions. We give up none of our capabilities, just as with Cuba—we're not giving anything up by having an embassy, by having diplomatic relations, and we can test whether that’s a better policy or not.

Goldberg: But in the meantime though, it’s fair to say that the Iranian regime is less on its backfoot right now because the money that’s been released—I mean, it’s their money but it was frozen in our accounts—the money has helped buttress that regime. You maintain your ultimate military capabilities, but your economic leverage is less today over Iran than it was a year-and-a-half, two years ago when the sanctions were really crippling their economy, no?

Rhodes: Well, with respect to Cuba, again I think they’ve found ways to survive in very difficult economic circumstances, so we don’t think economic pressure was a driver of political change there. With respect to Iran, they get that sanctions relief if they abide by the terms of the deal, and we think that’s a good deal for us. An Iran without a nuclear weapon, we can verify they’re not getting a nuclear weapon, is worth giving them that sanctions relief. But we can turn it back on, the sanctions, if they violate the deal. You know, the difference, the important difference with Cuba, is the Cubans took a leap in reestablishing diplomatic relations with us and saying they’re going to normalize relations. They had existed in an anti-American space where they justified their regime in some ways in opposition to the United States. They’re now doing something very different.