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    “I Was Duped. I Was Used.”

    In 2009, an American aid worker seeking to provide internet service for Cubans was thrown in jail for more than five years. Now, as relations with Cuba finally thaw, the imprisonment of Alan Gross remains a prime example of how promoting American values in countries that don't want them is a policy that is as well-intentioned as it is poorly executed.

    The Villa Marista prison in Havana is a complex of ornate, industrial-era buildings situated on the outskirts of the city. Before Fidel Castro came to power, in 1959, it was a Catholic boys school, but today it serves as the country’s main detention center for political prisoners. A fearsome place, its cells are cramped and dank, with beds made of iron planks hanging on chains, and a filthy hole in the corner of each room for a toilet. The prison guards are known for brutal interrogations and creative acts of petty cruelty; the lights are often kept on throughout the night, and in the evening an inmate might be served his breakfast and told it is morning.

    One night in early December 2009, a genial, portly 60-year-old man from Potomac, Maryland, was pulled out of his hotel room in central Havana and dumped into one of those cells. Alan Gross had arrived in Cuba a week and a half earlier on a U.S. government–backed mission to bring uncensored internet access to Jewish communities on the island, and was scheduled to fly home the following morning. He wouldn't make it back to the U.S. for more than five years.

    Gross had come to Cuba to espouse and spread the values and benefits of democracy by helping to make internet service more accessible; he had visited synagogues and Jewish leaders across the country, introducing them to search engines and Spanish-language Wikipedia. ("I saw the world," one of his beneficiaries later reportedly said, after being shown Google Earth for the first time.) For this, he was convicted of undertaking "a subversive project" to "destroy the Revolution” in Cuba, and sentenced to 15 years in prison. U.S. officials protested strongly, characterizing Gross as a humanitarian. Last December, on the same day the Obama administration revealed plans to restore diplomatic ties with the Cubans, after nearly six decades of impasse and isolation, it announced that Gross would be coming home, too.

    Aside from a few off-the-record appearances and a single interview, Gross has not spoken publicly about his experiences, and he rejected numerous attempts to be interviewed for this article. (A book deal and network television interview are believed to be in the works, and his website lists a contact for a speech agent. A $3.2 million settlement with the U.S. government, finalized late last year, came with a strict nondisclosure agreement.) But since returning to America, he has emerged as an advocate for closer U.S.–Cuban relations, and has a lively presence on Twitter, where he shares artwork he drew while in prison and observations from his recovery and reintegration into everyday life. In early June, after Republican Sen. Marco Rubio, a hard-line opponent of open relations with Cuba, threatened to block the appointment of a U.S. ambassador to the island, Gross quipped, "When will Sen Rubio recognize that significant on-the-ground changes are taking place in Cuba under his nose?" He's even embraced the snappy tone of social media: When a critic accused him of having Stockholm syndrome, he replied swiftly, "Not a fuckin' chance."

    Gross' resilience is striking. Friends and others who have seen him since his return describe him as having retained his upbeat attitude and lively sense of humor. (In a phone message he left for a supporter near the end of his captivity, Gross chuckled and apologized that it "took me so long" to get in touch.) But his writings and legal documents from the five years of wrangling over his case in Cuban and American courts, and interviews with friends and colleagues, tell a story of great anguish, and occasional bewilderment. "I have never — repeat, never ever — been in any kind of trouble, legal or otherwise, anywhere in the world," Gross noted in a handwritten statement he filed before a Cuban court in 2011. "I did nothing in Cuba that is not done on a daily basis in millions of homes and offices around the world. I have an immense fondness for the people of Cuba, and I am deeply sorry for being a trusting fool. I was duped. I was used. And my family and I have paid dearly for this."

    During the five years he served, he lost more than a hundred pounds, and many of his teeth. (He was often brought food infested with bugs; in a rare interview he gave to Moment, an obscure Jewish interest magazine, earlier this year, he said, “I had a policy that if it moved, I wouldn’t eat it.") His wife, Judy, a social worker at a hospital outside Washington, D.C., plowed through their savings, eventually selling the family home in the suburbs and moving into a small one-bedroom in the city. Gross missed the wedding of one of his daughters and the funeral of his mother, who died of cancer in 2014 (Cuban authorities repeatedly denied his requests for a final meeting). He reached the limits of his endurance, at one point inscribing his prison number, 243444, on his arm, as if it were a tattoo from a Nazi concentration camp. Toward the end, he suggested he might be prepared to take his own life — or that the misery of his circumstances would kill him — and briefly refused to let his children visit. “I cannot bear them seeing me like this, a shadow of my former self, surrounded by men with machine guns,” he wrote in an open letter to President Obama in 2013. “If I do not survive imprisonment, I do not want this to be the last memory they have of me.”

    It now seems obvious that Gross was hardly the ideal choice to run a secretive program in a country so openly hostile to the United States, and ruled by a regime bent on keeping itself in power by total control over its population. A career development worker, he had decades of practice building communications networks in dangerous, remote places, but almost no prior experience in Cuba, and no familiarity with Spanish. Over the five trips he would make on behalf of the government, his behavior — described by observers alternately as gratuitously clandestine or careless — exposed him to dangers that might otherwise have been avoided. Since coming home, the small missteps have continued: He has said the interview with Moment magazine was an accident, after he misinterpreted the request of a family friend to meet for coffee; he also tweeted his home phone number during an exchange with a cable company.

    But the errors made over the course of Gross' travels to and from Cuba go beyond his own. Gross was hired to do the job by a multimillion-dollar corporation, Development Alternatives Inc. (DAI), which was itself operating on a generous, $28 million contract from the U.S. Agency for International Development (USAID). From these funds, DAI and USAID shelled out $258,274 to Gross for his initial work, and then, just a few weeks before his arrest, approved another $332,334 for a second year. Under the contract, Gross was expected to provide certain markers of his progress: how many internet portals he created, the number of people who logged on, how much data they used. But no one, it seems, asked of him or DAI critical questions about the project's wisdom, or its likelihood of achieving its overarching aim: increasing democracy on the island. "No one at USAID got paid to look at this and say, 'This is a really bad idea,'" said Stephen Kaplitt, a former USAID attorney and a consultant to Gross' legal team. "No one had it in their job description."

    The Cuban government alone made the decision to arrest an American aid worker, and keep him in prison for five years. But how things got that far is a question that still troubles many of the Americans involved. Gross' release has been seen as a closing chapter in the tumultuous standoff between the U.S. and Cuba, but even as the embargo heads for an exit, and embassies set to reopen, the actual policy that dispatched Gross into peril remains largely unexamined, and a sticking point in current negotiations. That program, which is illegal under Cuban law, had been designed, years earlier, to bring freedom and rights to the population, in a manner that might expedite the downfall of the Cuban government. This goal had been embraced by George W. Bush, who made no secret his affinity for coercive regime change campaigns, but the appeal of its rhetoric was much broader. It was initiated by Bill Clinton, who first saw the value in putting money into dissident groups in Cuba. And it continued under Barack Obama, who came into office promising to remake America's role in the world, but took few steps to re-evaluate this particular component of his nation's affairs — not during his first year in office, while Alan Gross traversed Cuba, and not in the years since.

    Fulton Armstrong was at his desk in the Dirksen Building of the U.S. Capitol when word of Gross' arrest reached him. Armstrong, a 60-year-old former CIA analyst who worked extensively in Latin America in the 1990s, had recently taken a position as the top Latin America aide for the Senate foreign relations committee, under Sen. John Kerry. With his neatly parted white hair, broad shoulders, and soft belly, Armstrong has the rugged and impatient character of a retired athlete. For years he has been vexed by — some would say obsessed with — the problem of Cuba, and by his belief that America’s attempts to impose democratic values on the island had only helped to entrench the Castro government’s hold on power. (After 9/11, he clashed bitterly with Bush administration officials over their insistence, later proven inaccurate, that Castro was building secret stocks of biological weapons.) But only since emerging from the black world of intelligence, in the mid-2000s, has Armstrong been able to express himself freely on the matter, something he does now with little regard for political niceties. “A lot of Cuba policy is what jerk can provoke the other jerk to do something terrible first,” he told me recently.

    In the years following Castro’s socialist revolution, America adopted a two-pronged approach to the island. In 1961, the U.S. cut off diplomatic ties; a punishing economic embargo, formally instituted in 1962, all but halted trade and tourism between the two countries. Meanwhile, in the '80s and '90s, the U.S. launched a series of informational and developmental programs designed to fortify democratic opposition groups and undermine the regime’s stranglehold on news. Universities in Miami received money to train Cuban journalists in proper investigation and news-gathering techniques, and to fund prominent dissidents. A number of nonprofits were authorized to send humanitarian aid to the family members of imprisoned dissidents. Radio Marti, a U.S. government–run, Spanish-language news station started in 1983, broadcast to the island from a transmitter on the Florida Keys.

    This rubric of activities, run mainly out of USAID, is known as democracy promotion, and it has grown into a signature component of American foreign policy, and a major industry, worth hundreds of millions of dollars in grants and contracts each year. (Federal funding for Cuba alone peaked in the 2000s at $45 million per year; it is currently around $20 million.) Born in its modern form out of the collapse of the Soviet Union, American democracy promotion schemes have invested hundreds of millions of dollars into opposition movements and post-authoritarian societies, everywhere from Romania to Burma to Egypt. In some cases, the work is technocratic: Experts advise emerging republics on how to establish independent judiciaries, or write a constitution. But in closed or authoritarian countries, the work can take on a subversive edge. In the run-up to the 2000 ousting of the Serbian dictator Slobodan Milošević, for instance, USAID and its partners funneled money to the country's main opposition group, Otpor, helping activists purchase the cans of spray paint they used to plaster the group's slogan across the capital.

    Many cheered USAID’s early success stories, but Armstrong watched the rise of the program warily. The rhetoric of its political champions implied a certain neutral benevolence — after all, who could object to freedom and democracy? — but the approach, especially where Cuba was concerned, seemed needlessly antagonistic and covert. It also made little allowance for local perceptions, or history: After all, for decades, the U.S. posture in Latin America had been to tip the scales of power in the other direction, helping oust popularly elected, leftist governments through secret machinations in places like Guatemala and Chile.

    Over many years of travel and work, Armstrong has emerged with a different view: “Change has to come from within the system.” On postings overseas, Armstrong observed as lasting democratic progress seemed to emerge not at the prodding of outsiders, but through the activism of motivated insiders, many of them with nuanced relationships with ruling authorities. Without a more sophisticated game plan, attacking the autocracy and alienating its associates — morally satisfying though it may be — rarely seemed to produce the desired effect. “Maybe there can be some intellectual leadership from outside, but change has to come from inside," he said. "So if you have a policy focused only on the people who have pledged to dismantle the regime, that is a huge flaw.”

    In recent years in Cuba, there were hints that something like this might be playing out: After an ailing Fidel Castro turned over control of the government to his less charismatic brother, Raul, in 2006, younger Cubans seemed to increasingly pine for the advantages promised by free trade and modern technology. Edgy, popular bloggers, like Yoani Sánchez, began to openly voice their aspirations and disaffections online, challenging the regime to respond.

    But dissident groups in Miami and their congressional allies in Washington were fervently committed to the strategy: isolation and confrontation. A law, known as the Helms–Burton Act and passed in 1996, helped hold the policy in place: It not only reinforced the embargo, but it also linked the one main exception to the blockade, support for "democracy-building efforts," to a larger goal of regime change. Armstrong was skeptical, and often found himself engaged in vitriolic disputes with politicians of the anti-Castro wing over his attempts to scrutinize the pro-democracy projects at USAID. "We knew that there was a lot of stuff happening, but USAID wouldn't tell us the details,” he said.

    When he first heard whispers on Capitol Hill about an American aid worker who had been detained in Cuba, Armstrong started making calls. USAID could tell him nothing; the State Department initially claimed the man was not working for them. (The State Department would not comment on this). The project seemed to have no direct oversight in Washington, no close observation. Even down in Cuba, the absence of information was striking. At the end of December 2009, after Gross had been in prison for almost a month, he received a visit from a consular official from the U.S. interests section. In a cable to Washington, later released by WikiLeaks, the consular official reported that Gross appeared to be in "good spirits" and "his sense of humor is intact." But when Gross asked the official what she had been told about his mission to Cuba, the diplomat was blunt: She knew nothing about it.

    In early 2001, Gross founded a small international development company called the Joint Business Development Center. For the previous two decades, Gross had worked in the industry as an independent contractor, taking jobs from a growing network of private corporations that did government aid work overseas, often on lavish contracts. The attacks of Sept. 11, and subsequent campaigns of war and reconstruction, created a boom, and Gross seemed poised to benefit.

    The development field can be a harsh, grueling business, but Gross built a reputation for diligence and integrity; if anything, former co-workers say, he seemed to lack the cynicism that girded so many of his colleagues. “Alan is an uncomplicated guy,” said Wes Weidemann, a retired development contractor who employed Gross on a number of USAID projects during the '80s and '90s. “He was invested in what he did, and his motives were idealistic.” Born on Long Island, in 1949, into a working-class Jewish family, Gross grew up in Baltimore, where his father started a window-cleaning business. When he was old enough to attend college, Gross took night classes and spent his days with his father at the shop. Over the next few years, his career migrated toward international causes. He completed a master’s degree in social work at Virginia Commonwealth University and moved to the D.C. area, where he became involved with Jewish outreach charities like the Jewish Federation of Greater Washington, which helps support Jewish communities around the world.

    In 2005, Gross traveled to Israel under a grant from the EastWest Institute, a New York–based think tank. The assignment was to examine the possibility of constructing a free-trade zone outside of the main entrance to Gaza, where Israel would permit Gazans to more easily sell crops or acquire products from abroad. Reem Aloul, a former Jordanian development worker who undertook the campaign along with Gross, said she came to see the project as a long shot, owing to the political sensitivities of the region, but she noticed that Gross displayed few of her misgivings. “He was genuine about making a difference, and you don't often find that, quite frankly,” Aloul told me recently. “Sometimes I thought he was — naïve is not the right word — but he genuinely believed things could work when I or others would think, This is way too complicated.”

    Gross did his first job in Cuba in 2004, for a D.C.–based nonprofit in Cuba: According to a Cuban court, he delivered a video camera to an island dissident, and was paid about $400. (Gross, in an affidavit he later filed in U.S. court, said he delivered only medical supplies.) He spent a few days on the island, and loved the place, his wife later told reporters, and for many years he yearned for an opportunity to go back. That moment arrived in fall 2008, with an email from an official at Development Alternatives. In recent years, Gross had built an expertise in satellite communications in remote places, installing internet linkups for humanitarian aid groups in Iraq and Afghanistan. DAI hoped he could do the same in Cuba. There was some urgency: The Bush administration was nearing its end, and, according to notes later released in court, a USAID official told DAI staff members that they “definitely” wanted to see results before the middle of January — that is, before a new president was inaugurated. (A DAI official would later tell Gross, during a meeting at the company’s headquarters, to remove an Obama 2008 sticker from his laptop.)

    The first trip on behalf of DAI, in March 2009, came together somewhat haphazardly: An academic offered ideas for software; a Jewish outreach official in New York suggested contacts in Havana; a rabbi in Washington introduced colleagues who'd traveled to Cuba. The path from America’s Jewish congregations to the 1,500 or so remaining Jews of Cuba was a well-trodden one. Since a series of liberal reforms opened up access to religious communities in the mid-'90s, American Jews have made regular pilgrimages to the island, ferrying religious supplies and donations, often including electronics like computers or cell phones.

    The Jewish officials who Gross met in Havana, like the others who followed, have all since said (in Cuban court and to the media) they assumed the American visitor was just another of the Jewish volunteers. Gross, they say, made no mention of a contract with the U.S. government. Still, some noticed that his work seemed unusually sensitive. Gross typically brought with him a kit that he called “telco-in-a-bag” — a relatively advanced suite of electronics and connectivity devices that included a MacBook, a satellite-internet router called a BGAN, and a smartphone, all stuffed in a plain backpack. (After he was arrested, Cuban authorities traced almost 90 pieces of electronics and hardware to his various visits.) The idea was to create a connection to the internet that drew data from satellites — thus circumventing Cuba's censors — and then to build closed, secret networks that would allow nearby islanders to access it.

    Gross stayed in Havana on his first visit, but in April, on his second, he traveled to the southeastern coastal city of Santiago de Cuba. There, in a place that receives fewer foreign visitors, the Jewish leaders appeared to be more anxious about his proposal. According to Gross’ court filings, one of the town’s religious leaders told him that by letting him install an unregistered internet router in their synagogue, they were “playing with fire.” Gross also had his own troubles along the way: Worried that a piece of satellite equipment was too bulky to avoid breakage or detection, he left it behind in Havana. For this shortcoming, DAI docked his invoice for the trip by half.

    Back home in Maryland after that trip, Gross paid a visit to Elhanan “Sunny” Schnitzer, at the Bethesda Jewish Congregation. He was starting to see that the project would require a lot more willing recipients, and he hoped that Schnitzer could connect him with some.

    Schnitzer, a raffish, 62-year-old Reform rabbi with bright eyes and a puffy cloud of light-brown hair, was familiar with this sort of work in Cuba. For years, he led those religious missions to the island, and he has developed a fine sense for the vagaries of semi-sanctioned aid work in Cuba — “the red lines and the dark-red lines,” as he puts it. Something about Gross’ operation struck him as not quite right. Gross didn’t tell Schnitzer that he was working for the U.S. government, but the rabbi sensed that Gross was being a little too evasive. “It was very obvious to me that he knew he was doing something clandestine,” Schnitzer told me. Gross told him that he had been entering the country on a tourist visa, and didn’t speak Spanish. He also mentioned that he was traveling around the country in a rented car — rather than by bus or taxi through a Cuban government tourist agency, as might be expected for a humanitarian volunteer. “That was a red flag to me,” Schnitzer said. “That’s how you get yourself followed [by the authorities] in Cuba.” Still, Schnitzer wanted to help, and he sent Gross off with a letter of introduction to the president of the Jewish community in Camaguey, a city in central Cuba.

    According to Gross' affidavit, it was around this time that he began to voice concerns that his mission might entail significant risks — for him, or for the people he met along the way. (In addition to the Cubans he encountered, Gross also enlisted the aid of several American Jews, who were traveling to Cuba, to transport electronics. A few were named in Cuban court as accomplices.) At the end of May 2009, before he left for his third trip, Gross had a conversation with DAI in which he laid out some of his fears. During the conversation, notes of which were filed by Gross in court, he raised the possibility that he might be “PNG’d” — that is, deemed persona non grata, or deported — from Cuba before he could finish the job. Neither Gross nor DAI seemed overly concerned about any worse consequences, and the company asked only that he designate a successor who might take his place to complete the work. (DAI declined to respond to a series of questions for this article. Steven O'Connor, the company's senior director of corporate communications, said in a statement, "We're delighted that Alan is back with his family and we wish him the best in his work to support the improvement in U.S.-Cuba relations.") None of Gross' associates that I spoke with ever heard him raise the possibility of arrest.

    Still, as Gross later noted in the affidavit, it was becoming clear that the dangers were real. “Although I initially attributed their comments to paranoia caused by living in a country where the government strictly controls the population," he wrote, "I became increasingly concerned as the project went on that their comments were not unfounded.”

    In April 2009, around the time that Gross was embarking on his mission in Cuba, the top American diplomat on the island, Jonathan Farrar, sent a cable to his bosses at the State Department. Farrar, a career diplomat, had served extensively in Latin America, and spent many years working on democracy programs at the State Department. But when he examined the landscape of American democracy aid to Cuba, he was unsettled by what he saw: The dissidents being highlighted by the U.S. seemed to be the wrong people. They were old, out of touch, and, when they received U.S. funds, were mostly concerned with using it to preserve their own livelihoods. "We see very little evidence that the mainline dissident organizations have much resonance among ordinary Cubans,” he wrote.

    Getting the Cuba program right has proven notoriously difficult. A few years earlier, in 2006, investigations by the Miami Herald and the Government Accountability Office (GAO) revealed that the vast majority of federal funds designated for Cuba democracy promotion over the previous decade had been spent inside the U.S., often in profligate ways. Worse, few of the projects could produce solid evidence that their campaigns were having any effect whatsoever. At Florida International University, for instance, a $1.6 million program to train Cuban journalists had, over seven years, produced only four Cubans who completed the entire course. Another scholarship fund at Georgetown University, worth $400,000, resulted in just a single Cuban student attending the school over three years. Even Radio and TV Marti, the flagship programs of America’s information campaign in Cuba, sputtered. Despite investing more than $10 million over the previous year to send a television signal into the island — including hiring a private plane to fly overhead and beam signals from the sky — independent surveys put the maximum viewership on the island at fewer than 10,000 Cubans. (In a recent Univision poll, just 20% of respondents reported listening to Radio Marti in the previous week, the lowest of any station surveyed.)

    Beyond Cuba, a broader understanding of what works in democracy promotion has remained elusive. In recent years, USAID has undertaken a series of studies to evaluate the long-term impact of its own democracy promotion campaigns. The results of these and other, independent studies have been underwhelming. Several studies have found signs of a positive correlation between aid and democracy, but the gains they noted were often small; many others found no benefit at all. In almost every case, the academics complained that good data were hard to come by, and that proving a clear link between a specific program and a later uptick in democracy was all but impossible. (In recent years, it has become fashionable to posit that democracy benefits may be delayed, and thus barely noticeable until they suddenly and dramatically “reveal” themselves. That might help explain why a 2009 USAID inspector general report on democracy assistance to Egypt described the program’s impact as “limited.”)

    Margaret Sarles, a former USAID official whose job, for many years, was to collect and study the lessons inherited from decades of democracy promotion work in Latin America, told me she struggled to convince the agency to take an empirical approach to the task. “Some programs work, some don’t,” she said. “In the end, it is your hope, rather than your knowledge, that keeps you going.”

    The most intriguing study may be one from 2007, by a professor of political science at the University of Pittsburgh named Steven Finkel, which examined data from almost every USAID democracy promotion program between 1990 and 2003. Finkel found that the aid had what he called "clear and consistent impacts" on three elements of democracy (free and fair elections, conditions for civil society, and free media), but for a fourth, respect for human rights, he observed a downtick. He speculated that this "anomaly," as he put it, might be the result of statistical error, or improved monitoring by rights groups — or, possibly, a sign of a backlash effect.

    The idea of a backlash — of authoritarian rulers or hangers-on cracking down on human rights or free expression — has some precedent. In 1999, Thomas Carothers, an expert on democracy promotion at Carnegie Endowment for International Peace, published a study on democracy aid programs in post-Communist Romania. At one point, a Romanian politician who had been deemed too undemocratic to attend a U.S.-run training seminar told Carothers, “If you treat us like bastards, we’ll be bastards.” American officials, Carothers noted, tended to be oblivious to this side effect, repeating as a mantra that even if the programs don't do much, “at least we’re not doing any harm.”

    If there were an aspect of invention and disarray to Gross' work in Cuba, this attitude may have played a role. Carothers, who is no naysayer on the promise of democracy promotion (he believes many of its problems can be traced to bureaucratic dysfunction and underfunding), often writes that not nearly enough has been done to examine the lessons and failings of the past, or learn from them. “I think you can point to a number of cases where it has worked, but can also find cases where people say that heavy-handed assistance can be counterproductive,” Carothers told me. “The problem is there isn't a single answer.”

    After the investigations by the GAO and Miami Herald, policymakers did attempt to make some changes to the Cuba program. They restructured the way USAID spent money on the island, requiring that more funds be funneled through professional development companies, like DAI. But they made little effort to reconsider the amount of money being crammed into the system — in fact, around that same time, a Bush administration panel recommended increasing spending on Cuba transition programs to more than $45 million a year.

    Farrar’s memo had an impact as well. One of his proposals was that the Obama administration devote more resources and energy to encouraging “non-traditional dissidents,” like young musicians and bloggers. The administration did just that, lavishing praise in particular on the blogger Yoani Sánchez. As William M. LeoGrande and Peter Kornbluh note in their recent book, Back Channel to Cuba, Sánchez's rise in prominence through 2009 was accompanied by a worsening crackdown from the Castro government. That November, Obama made the extraordinary gesture of responding to questions posted on her website. Two weeks later, Gross was arrested.

    When Gross arrived in Camaguey, in June 2009, his obstacles seemed to only metastasize. In the countryside, where there was far less radio traffic in the air than there had been in Havana, unlicensed satellite signals proved harder to conceal from the government. In a report he later filed to DAI, Gross wrote that a government van with a long whip antenna periodically circulated in residential neighborhoods, attempting to “sniff out” out any unregistered frequencies. The Jewish leader that Schnitzer had put Gross in touch with there was a venerable rabbi named David Pernas Levy. Pernas Levy had been enthralled by the potential of the internet — he was the one who would later remark on being shown "the world" by Gross — but like the others, he cautioned Gross that accepting the internet connections posed significant danger.

    There was another problem, although it's not clear if Gross recognized it: The Jewish groups Gross was working with weren't exactly anti-Castro. Years of receiving perks and privileges from the government had established something of a détente between the Jewish community and the Castros — they even had some of the best access to technology like cell phones and email of anyone on the island. ("They're some of the most connected on the island," said Dina Siegel Vann, the director of the Institute for Latino and Latin American Affairs at the American Jewish Committee. "Castro always had a good relationship with Jews.") Pernas Levy is a good exemplar. According to the Cuban-American anthropologist Ruth Behar, who interviewed him while reporting a book, he spent the '60s fighting in counter-revolutionary battles across the island, and later joined in Cuba’s expansionist campaigns in Angola. He was, she wrote, “a man of unquestionable revolutionary credentials.”

    Gross nevertheless trudged ahead. That fall, after his fourth trip to Cuba, DAI asked him to prepare a proposal for a second year of work, and informed him that its projects would have to undergo a formal evaluation. Debra Gish, a longtime Latin America development consultant based in Guatemala, was asked to do the job. When she first saw the description of DAI’s activities, including Gross' internet scheme and a half dozen others, Gish told me recently, she was intrigued. “I thought, This sounds neat," she said. “On the surface it looked like any other project I’ve worked on in post-conflict countries to begin the organization and strengthening of civil society.” When she spoke briefly with Gross, while he was back in Maryland, she thought he seemed "very excited about the project."

    But after a series of inquiries, Gish found herself growing uncomfortable with the task. She couldn't get the information she needed from DAI about whom exactly it was working with on the ground; it was possible there weren’t any partners at all. “I assumed there was some kind of cooperative agreement between — if not the Cuban government — at least some entity or organization on the ground, who would be the counterparts to these activities,” she said. “Because that's how this works. Building civil society in Cuba is a whole different ballgame. It doesn’t exist, in a traditional sense, and you’ve got to have some sort of local understanding about how to build it from nothing.”

    Gish turned down the job, but Gross carried on. That November, he flew to Havana for the final time.

    A few months after Gross’ arrest, in the summer of 2010, Fulton Armstrong had a moment of optimism. For several weeks, he’d held informal discussions with Cuban officials about what it might take to get Gross released. The officials, Armstrong said, kept returning to the subject of democracy promotion. “The Cubans asked us for two things,” Armstrong said. “One, they wanted to be provided with an adult to talk to, someone who would give them some respect. Two, they wanted us to cut the crap with the democracy promotion programs.” (Defenders of the program often pointed to the Cuban government’s aggravation as evidence that it was working.) Supported, he said, by the State Department, Armstrong negotiated with USAID and the Cubans for a reduced package of funding for the projects, cutting them from $20 million to about $15 million per year. Armstrong was satisfied, as were the Cubans. It seemed like a sign of positive momentum. But it didn't last long. When Sen. Robert Menendez, a vociferous backer of Cuba democracy aid, caught wind of the talks and proposed cuts, Armstrong said, he stepped in and insisted they be undone. (A spokesman for Menendez declined to comment on the episode, saying only that the senator "has led the charge" to "secure appropriate funding levels" for Cuba democracy programs.) The talks tapered off.

    Indeed, despite the shock of Gross’ arrest, the program to push democracy on Cuba continued more or less unabated. At least three new schemes that were introduced to the island in 2009 continued in the years after Gross’ arrest. One, a Twitter-like social networking application called ZunZuneo, was designed to build up a Cuban user base and ultimately encourage them to use it to express dissenting viewpoints. Other plots involved dispatching youth civil-society activists from other Latin American countries into Cuba, and recruiting popular Cuban rappers to incorporate anti-Castro lyrics into their tunes. The programs were all managed by a private development corporation, Creative Associates International, and all took place in the four-year period after Gross started his own project. According to the Associated Press, which broke the news of the schemes in 2014, ZunZuneo didn't shut down until late 2012, when it ran out of government funding. At least in the case of ZunZuneo, users were never informed that they were participating in a U.S. government–funded project. Sen. Patrick Leahy, a frequent critic of the programs, later bashed ZunZuneo as “cockamamie” and "dumb, dumb, dumb.”

    Leahy was one of several lawmakers who visited Gross in prison over the years, and each time he returned more convinced that it would take a deal, rather than more pressure, in order to get him out. (David Dreyer, a Cuba policy veteran who met with Gross as part of a separate congressional delegation in the spring of 2011, told me Gross boasted of his impromptu exercise regimen — pushups and 10,000 daily steps around the circumference of his cell — but that he also looked unhealthily thin. “I kept thinking, Skin and bones, skin and bones,” Dreyer said.) “As far as I can tell, USAID and the Obama administration has all but forgotten about him," Leahy said during a hearing in 2014 on USAID funding. “It is long past time for the administration and the Cuban government to negotiate a resolution of this ordeal, so Mr. Gross can return home.”

    In the end, that is exactly what happened. Starting in the summer of 2013, Ricardo Zúñiga, an attaché for the Obama administration, and Ben Rhodes, Obama's top foreign policy aide, held talks in Canada with Cuban diplomats, focusing on the possibility of re-establishing ties between the countries. That December, in a dramatic moment, Obama publicly shook hands with Raul Castro during the memorial service of Nelson Mandela, in Johannesburg. A year later, the talks reached their conclusion: The U.S. and Cuba would announce plans to end the embargo and restore diplomatic relations. At the same time, the two countries agreed to a swap of political prisoners, including a handful of Cuban and American spies — and Gross. At the insistence of the U.S., Gross' release was characterized as an unrelated, "humanitarian" gesture. He returned to Washington on Dec. 17, 2014.

    That afternoon, Gross stepped gingerly up to a podium at the offices of his longtime lawyer, Scott Gilbert. Gilbert had worked on elements of the case, pro bono, for nearly two years, but only in the past year or so had he assumed responsibility for negotiating Gross' release. He'd come into the case with a background in Cuban history, and he quickly broke from the animus of his predecessors — one of whom had petitioned a United Nations human rights panel to declare Gross' detention unjust and arbitrary — opting to communicate less combatively with the Cubans. “You can't beat on a government that you've boycotted for 60 years," he told me. "That's a legacy of an old way of thinking — a total dinosaur.”

    At the podium, Gross beamed, his mouth a mostly toothless crescent. He turned to look at the two American flags perched behind him, as if in disbelief. "This is great," he said, and he took a deep breath.

    Earlier this year, I was in Miami, on the campus of Florida International University, to attend a vigil for a Cuban dissident group called Brothers to the Rescue. In the mid-'90s, at the height of the crisis over Cuban rafters, or balseros, fleeing their country in droves, activists with Brothers to the Rescue flew small planes around Cuban airspace, dropping anti-Castro leaflets over the island. One day in February 1996, four pilots were killed when their planes were shot down by the Cuban air force, and every year since, friends and family members have turned out for a moment of silence to honor their passing.

    Orlando Gutierrez, the national secretary of Directorio Democrático Cubano, one of the top dissident groups, had invited me to the event. Gutierrez is an imposing figure — he is tall, with a bald head and a stern face; when we first met, in a conference room at his office in Miami, he never removed his black leather jacket. Gutierrez described America as "an uncertain ally" of democracy in Cuba; the recent Obama administration decision had disappointed him deeply.

    The passionate activism of people like Gutierrez has always been at the heart of the Cuba democracy promotion program. Exile from their home country, and the ongoing abuse of their fellow dissidents, bring a moral clarity to their view, and a kind of urgency — it is a large part of why the democracy program has proven so stubbornly difficult to reform. Gutierrez wanted me to know that a change in official policy would not make decades of grievance disappear. “This is our family,” he said. “This is our home. It's not something we leave to go home at 5 p.m. It's something that is with us all day, something we work on every day.”

    At FIU, about 50 people had turned out for the vigil. It was a typical Florida late-winter day — warm, with a light breeze and a hint of the looming mugginess of summer. Students from a Cuban-American activity group set up a folding table with ice water and easels for posters displaying pictures of the four deceased pilots. The posters said “Murdered by the Cuban Gov’t.” They kept falling over in the wind.

    Arnaldo Iglesias had been in the third plane on the day of the shoot-down, and now he stood near the water table, chatting with old friends. He had bone-white hair and walked with the aid of a wooden cane, hunched over slightly in jeans and brown loafers. Obama's recent decision, he said, made him “extra sad” on a day that perennially brings him sorrow. “The past 20 years have gone by like that,” he observed, snapping his finger. “We were just young kids.”

    I asked Iglesias if it had ever crossed his mind that he might be shot down on the day he set off for Cuba.

    “Did we think we were risking our lives?" he said. "No.” He pointed to an elegant woman standing beside him, and said that she had been in the cockpit with him that day. “If we thought that, we wouldn’t have taken her. We just wanted to help, to save some balseros. I never thought they would have done that to us — maybe there was a risk of being fined, but to be shot down? Never.”

    As the ceremony started, the attendees stood in a circle around the fountain, holding hands. At the moment the attack started, 3:21 p.m, the gathering grew silent, and stayed that way for seven minutes, until the last plane would have been downed. Off to the side, Iglesias sat on a bench, looking solemnly at the ground. Brown-rimmed aviators concealed his eyes.

    USAID officials are unapologetic about the work they do to spread democracy, and when I met earlier this year with two in Washington — neither of whom would speak on the record — they told me that political ends would always have a place in development. “We pursue it as a means," one of the officials said, "because we believe — this administration believes, and it’s been a bipartisan belief of many administrations — that the protection of human rights and the building of democratic governance also directly contributes to social and economic progress."

    Nevertheless, the agency says it has begun to re-evaluate the way it conducts itself in countries where, like Cuba, there are less-than-friendly relations, ruled by dictators willing to go to great lengths to stay in power. That process is underway. As for working with dissidents in places where they may be at risk, the official said, “We think if they're willing to take the risk, and we can in a safe way, with our developmental partners, provide them the tools to stay safe, then we're willing to take the risks.”

    The policy can be hard to reconcile with the message from President Obama. This April, when Obama met with Raul Castro in Panama, he appeared to allude to the policy’s potentially negative consequences, saying, “So often, when we insert ourselves in ways that go beyond persuasion, it’s counterproductive, it backfires.” But in press briefings, the State Department has repeatedly said, seemingly in a nod to domestic politics, that the new policy “does not for a moment” mean that the U.S. is “lessening our emphasis on human rights, on democracy, on the importance of civil society." Indeed, just five days after Gross was released, the State Department posted an advertisement for a new, $11 million grant for Cuba. Its purpose: to “strengthen on-island, independent civil society capacity to further the rights and interests of Cuban citizens.”

    If any of these ongoing schemes to spread democracy in Cuba involve plans to sneak internet routers onto the island, recent days have shown there's an easier way. In March, the Cuban government approved for the first time free public Wi-Fi access in Havana and called for 50% of Cubans to have internet access by 2020. And in mid-June, executives from Google visited the island to discuss investing in networking infrastructure. They entered on business visas.