by Ben Rhodes
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OBAMA’S TRIP TO HAVANA would be in March, because he wanted it to coincide with Sasha and Malia’s spring break. Every detail of the trip—from the policy changes we were both pursuing, to supporting the American businesses trying to get into Cuba, to the intricacies of Obama’s schedule—was a subject for painstaking negotiation, in endless Skype sessions and multiple trips to Havana.
At the end of one of our meetings, Alejandro asked to see me alone. They had one dramatic proposal that they wanted me to explore. “We are very interested in Guantanamo,” he told me. “We know of President Obama’s interest in closing the prison. And so we would propose to take custody of Guantanamo.”
I started to say, as I had many times, that Obama’s priority was closing the prison, that we couldn’t even talk about the naval base. He cut in. “We take note of your difficulty in removing prisoners.” We were still haggling with other countries to take one or two detainees who were cleared for transfer. “Cuba is prepared to make the security requirements to hold them.”
It dawned on me what he was proposing—that Cuba would take all of the prisoners if we gave them back the naval base, a piece of Cuban territory that had been occupied by the United States for more than a century. Each year, the United States gives Cuba a check for a few thousand dollars to pay for the facility; the Cubans never cash it. “I just want to be clear here,” I said. “You are offering to take all of the prisoners?” There were, at that time, nearly a hundred.
“Cuba is very good at holding people securely,” he said.
“There are some that we’d need to remove,” I said, thinking of Khalid Sheikh Mohammed, the 9/11 mastermind. We’d been prevented from transferring him and others to prisons in the United States because of laws passed by Congress. Teams of lawyers had looked at other possibilities, including holding them in U.S. territories such as Guam or Puerto Rico.
“Whatever you need to do,” he said.
For the rest of my time in government, there wasn’t a meeting when he didn’t revisit this idea. Even as I knew it was unlikely to happen, I came to like the idea, and I told Obama so. We could have some negotiated transition period, where the United States and Cuba jointly administered the facility. In meeting after meeting on Gitmo, I’d hold up my hand and say, “I’m the only one with a Plan B.” Obama dismissed it as a bridge too far, even for the fourth quarter. But I couldn’t help but see the unintentional genius in the idea—righting two historical wrongs, ending two chapters at once.
* * *
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DURING ONE LENGTHY DINNER in Havana a few days before Obama was scheduled to arrive, Alejandro abruptly left the table to take a phone call. When he returned, he announced that he and I would now go to visit the president. He never once referred to him as his father. We left abruptly, piling into the back of a black BMW for the short drive to a large government building. A few plainclothes security guys stood in the lobby, as I was ushered into an underfurnished room where Raúl was sitting wearing a guayabera. We sat down, Oval Office style, with me in a chair adjacent to Raúl.
Raúl did most of the talking. A few minutes into the meeting, he took out a foldout map of Cuba and made me hold one end of it as we leaned over like two generals assessing a campaign. He began by tracing the progress of the revolution, from the Sierra Maestra mountains to Havana. He showed me various military airstrips that could be turned into civilian airports, and described their proximity to beaches and other attractive sites. Pointing to Cuba’s perimeter, he welcomed the Paris agreement, talking about the risk of climate change to Cuba’s outer ring of islands and keys. In his own way, he was showing me the outlines of a tourist economy that Cuba was building, an economy that depended upon an eclectic mix of state-run hotels and individually owned small businesses such as restaurants, shops, and taxis.
He pointed to a tiny speck of land south of Cuba. “There, I have allowed an Italian businessman to park a houseboat with five beds where he feeds sharks all day.” I nodded, not sure what to make of this anecdote.
“Caroline Kennedy was in my office the other day,” I said. “She noted that it wasn’t her father who had closed the embassy. That he’d inherited Eisenhower’s Cuba policy.”
Castro nodded. “Robert Kennedy’s son recently came to Cuba,” he said. “And even though his father tried to kill my brother, I let him stay on these beaches. I even let him stay with the Italian who feeds the sharks.” Somehow this anecdote seemed to reveal something essential about Cuba.
He returned again and again to the revolution, to the stories of how poorly the landing of the Granma had gone, and of how he and Fidel greeted each other: “I had five rifles,” he said. “When we came together he grabbed me and put his forehead to mine and said, how many rifles do you have? I said five. He said, I have two.” Raúl sat back and slapped his knees. “That makes seven rifles. So we will have to take them from the enemy. And that is what we did.”
I also knew that this talk of the revolution wasn’t just posturing, it was intended to show that he wasn’t going to compromise the revolution’s legitimacy. The talk of the evolving economy was intended to show that there was a streak of pragmatism to Raúl, one that his brother didn’t share.
I tried—again and again—to steer the conversation back to our demands. We wanted Cuba to expand its nascent private sector. We wanted Cuba to reform its economy, to allow foreign businesses to hire Cubans directly, and to show more restraint in its treatment of protesters. I began to enjoy playing this part, friendly but persistent.
“You know,” Raúl said to me, “a thought has occurred to me that I have never shared. The Americans like to give people candy.” He looked around the room, finding nodding agreement on his side. “They like to give people candy for doing whatever they want in Latin America. But Cuba is not interested in candy.”
After more than two hours of this, Raúl announced he would send me a copy of his own biography. “It’s by a Russian,” he said. “It’s good, but it also shows my flaws.”
“None of us is innocent,” I said, and he laughed.
I went through some of the remaining issues for our trip, including Obama’s planned meeting with dissidents. “Obama is welcome to meet whoever he wants in Cuba,” he said, waving his hand in front of him. “Obama is welcome in Cuba.”
As we neared the three-hour mark, we wound down the meeting. “It is hard for us,” he said, “being your closest neighbor.”
I corrected him. The Mexicans were our closest neighbor, and they liked to say of themselves, “So close to America, so far from God.”
He laughed, but in turn corrected me. “Look,” he said, pointing down at Guantanamo Bay Naval Base on the map in front of us. “We are your closest neighbor.”
* * *
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AS AIR FORCE ONE began its descent into Havana, Obama knelt next to me on the couch peering out the windows. I was nervous about everything, including some rain that had begun to fall, as if any blemish on the trip would be a personal failure. This felt like the capstone of my eight years in government; I wanted everything to go perfectly. As the outskirts of Havana came into view—thatched houses and corrugated shacks—Obama said, “That doesn’t look like a threat to our national security to me.”
By the time we touched down in Cuba, we’d announced the farthest-reaching changes in U.S. policy that the law would allow—enabling Americans to travel there for people-to-people engagement and authorizing more financial transactions in Cuba. We’d initiated direct mail service between the United States and Cuba for the first time in decades, with Obama himself responding to a letter from an elderly Cuban woman who had written to the White House. We’d arranged for a Major League Baseball exhibition game to be played during our visit, between the Tampa Bay Rays and the Cuban national team. We’d reached a slew of agreements to get U.S. businesses in the door in Cuba. We’d even
had Obama tape a segment with a Cuban comedian named Luis Silva, whose character Pánfilo featured on one of the most popular shows in Cuba.
As the trip approached, it had become clear that for all our focus on using the trip to maximize changes in policies, the symbolism and story of Obama’s visit were going to matter more. I had taken a trip down to Miami to do a series of meetings with leaders in the Cuban American community. It spoke to the raw feelings of some Cuban exiles that when I exited my commercial flight, I had a sizable police escort waiting for me that followed me throughout the day. In Miami, history was a present thing, and there were people who saw any rapprochement with the Castro government as an act of betrayal.
But over the course of the day, I heard a different message. To younger Cuban Americans, Obama’s policy was long overdue. The children and grandchildren of exiles didn’t carry the same baggage, didn’t see the future of Cuba as a competition between Castros and exiles. Some of the old hard-liners were changing, too. Carlos Gutierrez, who had been George W. Bush’s commerce secretary, had been transformed from a hard-liner into an enthusiastic proponent of engagement. “I just got tired of using the same talking points,” he told me.
What I heard in Miami, though, was a single message: The most important element of the trip was the speech Obama would give in Havana. Cuban Americans wanted to hear him make the case for democracy, for openness, and to include them in whatever story he told about Cuba. More than any other diaspora community I’d engaged with, Cuban Americans saw themselves as a people in exile. I asked them to share stories and cultural touchstones that would be meaningful for Obama to talk about, and for days afterward my in-box was filled with stories: people whose parents had put them alone on planes to America, people who had been separated from family for decades, people who opposed the government in Havana but clung to their connections with Cuba.
Cuba also seemed to attract a unique assortment of personalities that represented powerful threads from America’s own story. Ernest Hemingway had lived there for more than twenty years, and his grandsons reached out to me before our trip. José Andrés, the prominent Spanish American chef, came with us, as he had supported Cuba’s self-employed cooks. Jimmy Buffett made plans to play a concert. Jackie Robinson had played baseball in Havana, and we were joined on Air Force One by his daughter and ninety-threeyear-old widow, Rachel. It felt as if we were traveling to Havana with a cast of American underdogs and overachievers: Cuban exiles and the offspring of cultural icons; baseball players and singers; civil rights heroes; and, of course, an African American First Family. The delegation itself spoke for America.
As we rode in from the airport, the ambivalence of the Cuban government was on display. The government had apparently warned people not to line the route of the motorcade, to avoid too enthusiastic a greeting for an American president, but they had also repaired and refurbished the streets we drove on. As we passed cement block apartment complexes, I saw clusters of faces pressed against the rain-swept windows, peering out at something they’d never expected to see.
The rain built to a downpour as we pulled in to Old Havana. Obama went into the Catholic cathedral and was greeted by Cardinal Ortega, the man who had carried the pope’s personal message to the White House a year before. “I delayed my retirement for this,” Ortega said, clutching Obama’s hand in greeting. As we walked through the secured streets, people clustered in the windows of shops, smiling and waving, some holding miniature American flags.
* * *
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THE NEXT MORNING, ALEJANDRO was a mix of nerves and confidence. We met in the same government building where I’d spent dozens of hours over the past year, but this time I was traveling with a thousand Americans: staffers, security personnel, Cuban Americans, athletes, journalists, and assorted celebrities. Still, I had the feeling we’d be negotiating every aspect of the trip until the moment our plane took off. Sensing my own mix of fatigue and annoyance at having to meet so early, Alejandro declared that he had good news. They had agreed to our two remaining asks: that Obama and Castro do a press conference after their meeting, and that Obama’s speech be broadcast—uncensored—to the Cuban people. Neither thing had ever happened before in Cuba.
On the motorcade over to the Plaza de la Revolución, it seemed that the Cuban government had either relaxed its restrictions or lost some degree of control, as huge crowds greeted the motorcade.
After a lengthy meeting with Raúl, the press conference was a circuslike atmosphere. The Cuban journalists, all employees of state-run media, seemed astonished to see their own leader taking questions. Jim Acosta, the same reporter who had asked Obama why he didn’t get the bastards, stood up and said, “My father is Cuban. He left for the United States when he was young. Do you see a new and democratic direction for your country? And why do you have Cuban political prisoners?”
When it was his turn to answer, Castro looked momentarily confused. His grandson came over and whispered something in his ear. “Give me the list of political prisoners and I will release them immediately,” he then thundered. “Just mention a list. What political prisoners? Give me a name or names.” It was, in a way, great theater—the Cuban president forced to answer for his repressive policies—but I knew we were pushing the Cuban system hard, and that there would inevitably be blowback. This was the tension in our policy. The imperative back home was to push the Cubans on human rights, but that could backfire. We got fifty-three political prisoners out through quiet talks, not through denunciations. Pushing them publicly was not always the best way to get results.
After the press conference ended, the Cuban reporters all applauded. Castro shook hands with Obama and then tried to raise their hands together in triumph. Obama, not wanting to have that image plastered on front pages all over the world, let his hand dangle limply in Castro’s. It seemed an apt metaphor for our approach—engaging without embracing.
That night, I went to the house where the Obamas were staying. The Obama family was hanging out in the living room while he pulled me aside to review the speech. He’d barely edited it, deferring to me. “Do we have enough in here for the Cuban Americans?” he asked.
“I think I’ve talked to just about every Cuban in the United States,” I joked.
“Well, maybe punch up the point on reconciliation. People are people. Cubans are Cubans. Give it some lift.”
I went back to the quiet of my empty hotel room. I’d put everything I had learned about Cuba over the last three years into the speech Obama would give the next day, and I was happy with it. Usually, the night before a big speech, I’d sit on my balcony and read the words over to myself. Instead, I invited the team who had worked on Cuba with me—Ricardo, Bernadette, and Siobhan Sheils, a young staffer on Cuba—to my room. For a couple of hours, we drank Havana Club rum, read the speech out loud to one another, and told stories of our endless talks with the Cubans.
“Sometimes I think we underestimate how hard they are pushing inside this system,” I said to Ricardo. I knew that even if the Cubans weren’t making changes in exchange for candy, they had opened the door to America: our travelers, our businesses, the giant neighbor to the north, with our different ideology and way of doing things, and now our president.
“Yeah,” Ricardo said. “Hey, thanks for including me in this.” A few months earlier, he’d left the NSC for a posting in São Paulo. Before leaving, he told me something that he never had before about his father. I knew he had been a Honduran military officer who ended up on the wrong end of an internal struggle and was eventually killed, which led to Ricardo’s growing up in America and going to work for the State Department because he saw America as a force for good in a chaotic world. But the story was more complicated. Even though he came from a right-wing family, Ricardo’s father had become something of a reformer and whistleblower on corruption. He was pushed out of the military over his opposition to Honduran support for the Contra progra
m, and he was killed by the type of reactionary forces who had battled Cuban proxies across Latin America, a victim of the poisoned politics that we had set out to bury.
From my balcony, we looked out at the darkened Florida Straits that separated Cuba from the southern tip of America. Being there, in Havana, with this group of people who’d become like a second family, I felt better than I ever had before in my job. This is why you put up with everything.
* * *
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THE SPEECH TOOK PLACE at a grand theater that had been restored for the occasion. Raúl Castro sat in a balcony. The famous blind Cuban ballerina Alicia Alonso, for whom the theater is named, entered to thunderous applause. We’d fought hard to invite dozens of guests, including many Cuban Americans. Obama walked to the lectern and began with the words of Martí’s most famous poem, “Cultivo una rosa blanca.” From there, the speech broadened out to track both the story of sixty years, and my own feelings working on Cuba for the last three. “Havana is only ninety miles from Florida,” Obama said, “but to get here we had to travel a great distance—over barriers of history and ideology, barriers of pain and separation.” Covering the period from the revolution to the missile crisis to today, Obama said, “I have come here to bury the last remnant of the Cold War in the Americas. I have come here to extend the hand of friendship to the Cuban people.” The audience erupted in applause.
It was too much for me. I slipped out a back door to a side street, smoking, staring at dilapidated facades and old cars, the empty street frozen in time outside a theater where history was happening. I knew the notes he was hitting, having nearly memorized the speech myself. The tributes that Cubans would appreciate—to their education and healthcare systems, their stance against apartheid in South Africa. I knew the cultural touchstones that would unite people across the Straits—the music and dances and athletes. I knew the language that would resonate to the north: “In America, we have a clear monument to what the Cuban people can build. It’s called Miami.”
