The streets had darkened in Havana on December 3, 2009, as Alan Gross sat in his room at the Hotel Presidente, an elegant building located near the Cuban Foreign Ministry. It was 10 PM, and he had just gotten off the phone with his wife; they planned to have dinner together at their home in suburban Maryland the next day, when he was expected to return. Suddenly, Gross heard a loud knock at his door. Voices barked from the hallway, but Gross, who did not speak Spanish, did not understand. He opened the door and discovered four hulking security agents. Soon he was taken downstairs and forced into a compact car. He was under arrest. 

On the campaign trail in 2008 and during his first few months in office, President Barack Obama expressed his desire for a "new beginning with Cuba." Yet with Obama set to begin his second term, the relationship between the two countries remains largely unchanged. The single biggest reason for the status quo, according to the White House, is the dispute about Gross, who is still in Cuba serving the remainder of a 15-year prison sentence. Officials in Havana say that Gross was working for the U.S. government and trying to subvert the state. But from the beginning of the saga, the State Department has said that Gross was merely bringing better Internet access to Cuba's Jewish community. Speaking to a House committee in February, Secretary of State Hillary Clinton was adamant that Washington would not reward Havana for its "deplorable" conduct: "We've made no deals, we've offered no concessions, and we don't intend to do so." 

That might be true, but more than a dozen interviews with former U.S. officials, foreign diplomats, and other observers reveal that there has indeed been a U.S. government-led effort to bring Gross home. From the start, the talks have been mired in mistrust and miscalculation; each side seemed to be waiting for the other to blink. Eventually, however, the United States appeared to step back from an opportunity to free Gross from jail and strike a blow against the antiquated politics of the Cold War.

In the wake of Obama's re-election, some have high hopes for Gross' release and an improvement in U.S.-Cuba relations. But with a divided Congress peering over the fiscal cliff and preparing for other partisan battles, Cuba hardly seems to be a priority for the White House, and the United States' long-standing embargo against the island nation -- now more than 50 years old -- seems as firmly in place as ever. That does not bode well for Gross.


Not long after Gross missed his flight, Fulton Armstrong, a senior adviser to the Senate Foreign Relations Committee, began hearing rumors that an American had been arrested in Cuba. Alarmed, Armstrong started making calls, and, little by little, he pieced together the story: Gross had been setting up satellite Internet networks for Cuban Jews -- networks that the regime couldn't control. This service was sure to anger the Cuban government, which blocks a variety of Web sites that it deems threatening. Armstrong called the State Department to confirm what he'd heard, but State denied having a relationship with Gross. Over the course of several days, the story continued to change. One State Department official erroneously told Armstrong that Gross' mission was classified; another said that Gross likely worked for the Central Intelligence Agency. 

Having spent years as a CIA officer, Armstrong doubted that Gross worked for Langley. Gross did not speak Spanish, he knew little about Cuba, and he was having meetings in places known to be crawling with Cuban agents. Lo and behold, after several weeks, the State Department finally admitted that Gross was theirs. Bit by bit, Armstrong learned that in of 2009, Gross traveled to Cuba five times to fulfill a contract worth more than $500,000 for Development Alternatives Inc. (DAI), a Maryland-based firm, which was working for the United States Agency for International Development (USAID). 

Gross' mission, approved during George W. Bush's presidency, was part of a provocative USAID program created in 1996 by the Helms-Burton Act, which, among other things, allotted money for creating institutions and providing access to information outside of the government's control, in hopes of quickening the fall of Fidel Castro. In an interview with CNN's Wolf Blitzer this past May, Gross maintained that he went to Cuba simply with "some off-the-shelf equipment to test to see if it worked." He also decided to "try to improve the computer system within the Jewish community." Gross says he was not specifically helping dissidents. Yet working for the Helms-Burton programs is a crime on the island, and officials in Havana are especially sensitive about satellite Internet equipment; they have long memories of exploding cigars and "Yanqui invasions." What the Cubans seemed to fear was that Gross' project was a test mission for future operations. It's not clear if it was, but according to a $60 million lawsuit that Judy Gross, Alan Gross' wife, filed last month, claiming negligence against USAID and DAI, the development firm had a contract "to establish operations supporting the creation of a USAID Mission" in Cuba. 


When Obama entered office, a year before Gross was arrested, many Cubans had high hopes that the two countries could take steps to move past the Cold War. Initially, there were positive signs. In April 2009, Obama ended restrictions on Cuban-Americans traveling and sending money to the island and called for a thaw with Havana. The president later signaled his willingness to have high-level meetings with Cuban officials, and the State Department asked the U.S. Interests Section in Havana to turn off the electronic billboard hanging outside its fifth-floor windows, which for years had criticized the Cuban government in bright red letters. Meanwhile, the U.S. Attorney's office filed an indictment against Luis Posada Carriles, an elderly Cuban exile and former CIA operative, who had taken part in the agency's violent shadow war against Fidel Castro. Posada Carriles stood accused of lying to U.S. immigration authorities about his alleged role in a series of bombings in Havana in the late 1990s. 

For the United States, these were important policy changes; some analysts felt that a greater rapprochement was on its way. But the Cuban government adopted an attitude of wait and see. By fall, there had been little talk about easing the U.S. embargo or taking Cuba off the list of terrorist states -- two top priorities for Raúl Castro, who was by then in charge. Meanwhile, as social media helped propel the Green Revolution in Iran, the Cuban regime grew increasingly agitated that the White House had not put a stop to missions like Gross'. "President Obama has taken some limited measures on U.S. Cuba's policy that we have recognized as positive," Pedro Monzon, the Cuban ambassador to Australia, said. But, he continued, "The U.S. also didn't modify or stop ... illegal programs financed in order to promote the overthrow of the Cuban government."

In the spring of 2010, months after Gross' arrest, high-level officials from State and USAID decided that what happened to Gross was part of a wider problem: that the democracy programs were ineffective and poorly managed. "These programs don't help development," a former USAID official said. "They politicize things." 

For more than a year, Armstrong and his boss, Senator John Kerry, the head of the Senate Foreign Relations Committee, had been trying to reform the democracy programs, but with little success. Now State and USAID wanted Armstrong's help to create more transparency, and they wanted to fund efforts that would better help citizens of Cuba -- but without specifically targeting dissidents. They also hoped that cleaning up the programs could help bring Gross home.

In a series of confidential meetings throughout the summer, the State Department and USAID, along with Armstrong and others, agreed to only spend $15 million of the $20 million the government had allotted for 2010 to USAID on Cuba. There simply were not enough quality programs, they believed, to justify the expense. They also agreed that more cuts and changes would be in store. 

That summer, at State's behest, Armstrong began meeting with high-level Cuban officials from the U.S. Interests Section in Washington to tell them about the changes in the democracy programs. The meetings appeared to go well. "We said, 'Look, message received,'" Armstrong told me. "'These [democracy programs] are stupid. We're cleaning them up. Just give us time, because politically we can't kill them.'" The Cubans seemed appreciative. "We asked them, 'Will this help you release Alan Gross?'" Armstrong went on. "And the answer was yes." 

That fall, Armstrong began convening with State and USAID again, in a second set of confidential meetings, to hash out the 2011 budget for the democracy programs. Armstrong and his allies at State hoped that in the upcoming year, the United States would spend only $10 million of the allocated funds and make the programs even more transparent and apolitical. They also wanted to permit more religious, academic, and cultural groups to travel to the island, which had been a major part of the Clinton administration's Cuba policy. "These things are important," a former senior government official said. "It was Bruce Springsteen that brought down the Soviet Union. It wasn't Star Wars or anti-ballistic missiles."

This time, however, some of the bureaucrats in USAID began to push back, fearing that Armstrong and his allies at State were going too far. Insiders say that USAID bureaucrats began leaking information about their efforts to two powerful officials on Capitol Hill: Robert Menendez, the Democratic senator from New Jersey, and Ileana Ros-Lehtinen, the Republican member of congress from Florida. The two are part of a group known as the Cuban-American lobby -- and their constituencies include many families who lost everything during Castro's revolution. Both believe that isolating the regime is the best way to bring about its demise, and they began fighting against many of the changes. 

In the meantime, State continued efforts to get Gross out of prison. In September 2010, Spanish government officials helped arrange a secret meeting between Assistant Secretary of State Arturo Valenzuela and Cuban Foreign Minister Bruno Rodriguez in New York. The Cubans were far less flexible than the Americans expected. The U.S. took a unilateral approach:  it wanted Cuba to release Gross, and only then would it press ahead on any other policy changes. The Cubans were apparently not pleased; the Americans wouldn't offer them a firm commitment on anything. Rodriguez allegedly lectured Valenzuela for roughly an hour on Cuba's history of grievances. 

The State Department was disappointed; at a time when the Cuban government had announced major economic reforms, senior U.S. officials didn't know who was really calling the shots in Havana. They were nevertheless undeterred. In October, fearing that Cuba had once again become low on the White House's list of priorities, the Cuban Interests section in Washington sent word that Rodriguez wanted to meet with Kerry. With State's blessing, Kerry met Rodriguez at the home of Cuba's ambassador to the United Nations in New York. There was no quid pro quo, but the meeting seemed to reassure the Cubans that the democracy programs would change, and the Cubans expressed confidence that Gross would receive a humanitarian release shortly after his trial, which was scheduled for March.


It was 80-plus degrees in Havana on March 28, 2011, when former President Jimmy Carter stepped down from his airplane onto the tarmac. Carter, dressed in a white guayabera and black dress pants, had arrived at the personal invitation of Cuban President Raúl Castro. Both Carter and Castro tried to minimize expectations; they made it clear this was still part of a trust-building dialogue. And to build that trust, Carter called for an end to the embargo. 

Much had changed since the previous fall. The Democrats had been trounced in midterm congressional elections, and with a Republican majority in the House, Ros-Lehtinen became head of the Foreign Affairs Committee. Meanwhile, with the economy still sputtering, and with Republicans smelling blood, Menendez had more power than ever. "At the time, the Senate was so evenly divided that Menendez ... was able to hold virtually anything hostage to get his way on Cuba," Peter Kornbluh, a Cuba analyst at the National Security Archive, said. 

According to insiders, Menendez allegedly called Denis McDonough, Obama's deputy national security adviser, demanding, among other things, that the full $20 million be spent on the Cuba democracy programs and that some of the money still go to dissidents supporting human rights. McDonough was boxed in, according to a former government official. Some within the State Department weren't confident the Cuban regime was seriously willing to negotiate. And knowing that they would need Menendez's vote on a variety of issues, and with Obama's re-election efforts sure to be difficult, the administration gave Menendez what he wanted, according to several individuals with knowledge of the situation. "As much as I'd like to get out of this 50-year morass," a former government official said, "Menendez is just so willing to escalate."

On Carter's second day in Havana, as he and his wife met Castro at Havana's presidential palace, Menendez released a letter blasting the ex-president's presence in Cuba. Around the same time, word leaked that the State Department was indeed going to spend $20 million in 2011 on the democracy programs, and that some of the provocative Bush-era policies would be restored as well. "Poor Alan Gross," Armstrong wrote in an e-mail to colleagues. The Cuban-American lobby had won.

The timing couldn't have been worse. Insiders say that Castro had become mired in a fight with hard-liners in his government about his plans for economic liberalization. A week later, as Castro prepared to present his economic reforms to the Cuban Congress, a Texas court acquitted Posada Carriles on all charges. Analysts say that the Cubans were dismayed. In August of 2011, after Gross lost his appeal, there was no humanitarian release. By the fall, Cubans and American officials had basically stopped talking. 

No one can say for sure whether the Cuban government would have released Gross even if the democracy programs had continued to change. Some insiders think that he was never going to be released. Others, however, claim that what happened on Carter's trip had convinced the Cubans that the State Department either could not be trusted or had little room to maneuver. "We should have been smarter," a senior congressional aide said. "In a conversation between two folks who don't trust each other, you have to find measures of confidence. If what you make of that is, 'Well, I'm going to kick the chess pieces off the table,' that's just goofy."

Now, in the wake of Obama's re-election, a new chess match might be in the works -- one that analysts hope will win Gross' eventual release and improve U.S.-Cuba relations. Kerry will likely succeed Clinton as secretary of state, and Obama, who won Florida by a considerable margin, no longer has the campaign to think about. Although officials in Havana have reportedly acknowledged that Gross was not a spy, they have been hinting at a swap: Gross in exchange for five Cuban intelligence officers who were arrested in the United States in 1998 (the so-called Cuban Five) -- a position that many think is negotiable.

Yet there is also cause for pessimism. The Senate is less divided than it was two years ago, but as the Obama administration approaches the fiscal cliff and other legislative battles, Cuba hardly appears to be high on its list of priorities. And if Kerry takes the helm at State, Menendez may well become the head of the Senate Foreign Relations Committee, a position he could use to frustrate the White House on a number of fronts such as appointing ambassadors. "You have to be prepared to give something if you want to get something," Robert Pastor, a former adviser to President Carter, says. "Whether the administration wants to pay the price [for Gross] is a fair question." 

Judy Gross, for one, is not optimistic. After returning from her latest visit to Havana, she said that her husband, 63, is now staying in a prison hospital. He has become friends with his fellow inmates and often watches Cuban baseball with them on television. But she is concerned about his health, about the fact that he has lost more than 100 pounds during his time in prison. Her biggest fear is that U.S. policy will remain unchanged and that her husband could die behind bars. "Cuba has done a horrible thing, and I can't forgive it for that," she said. "But I feel betrayed by the United States. And Alan feels betrayed, too."

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