Late last year, when President Barack Obama and President Raúl Castro of Cuba were only weeks away from a stunning announcement that they were ready to end a half-century of hostility, White House officials negotiating the thaw learned of a problem that could derail their clandestine work.
A surreal subplot to the negotiations - a covert plan to allow a Cuban prisoner held in the United States to artificially inseminate his wife in Havana - had succeeded. But the woman, who is famous in Cuba, was now visibly pregnant. White House officials found themselves in the bizarre position of pressing the Cuban government to keep her out of the public eye for fear that her appearance would raise suspicions and upend the talks at a critical moment.
The story of America's reconciliation with Cuba that culminates on Friday with the ceremonial raising of the U.S. flag over a newly reopened embassy in Havana is one of near misses, crossed wires, political stalemates, freelance interference and unexpected challenges that could have changed the course of history. While presented with a flourish to a surprised world, the path to a diplomatic opening was very nearly a dead end.
Driven by the ambitions of a president eager to make a fresh start with a Cold War-era adversary and eventually blessed as a moral imperative by Pope Francis, it was fueled at crucial points by more human considerations: the mounting desperation of Alan P. Gross, an American government contractor jailed in Havana, and the wish of the wife of a Cuban man imprisoned in California to bear his child before it was too late. It was shadowed at every turn by suspicion and mistrust, calcified over decades.
The drive for reconciliation defied normal conventions, handled by just two White House aides who bypassed diplomats at the State Department. At one point in the summer of 2014, when White House officials feared that Gross might commit suicide in prison, Obama intervened directly by writing him a letter imploring him not to give up hope.
"When we initiated the discussions, we didn't know exactly where it would lead," said Benjamin J. Rhodes, the top Obama aide who, with Ricardo Zuniga, the National Security Council's top Western Hemisphere official, spent more than a year sneaking off to secret negotiations in Canada and finally at the Vatican. "The talks frankly ended up leading in all kinds of directions that we couldn't have anticipated in the beginning."
The United States broke off diplomatic relations with Cuba in January 1961, but every president since engaged in some form of talks with Havana, sometimes through secret channels or intermediaries, sometimes just over discrete issues. Jimmy Carter and Bill Clinton each made concerted efforts to transform the broken relationship only to be frustrated, leaving the two sides frozen in an ancient conflict long after the end of the Cold War.
Obama came to office determined to succeed where his predecessors failed, convinced that the trade and commercial embargo had failed to undermine the Castro government while worsening Washington's standing in Latin America. Campaigning for the White House in Miami in 2008, he told a Cuban-American group that he would meet with Castro "at a time and place of my choosing."
At his Chicago transition office after winning the 2008 election, the president-elect told Sen. Richard J. Durbin, a fellow Illinois Democrat, that overhauling American policy on Cuba was a priority, but the circumstances would have to be right. "I thought it is long overdue, and it will take this president to step up and do it," Durbin recalled.
Once in office, Obama moved quickly, easing family travel and remittance restrictions, expanding cultural and academic exchanges, and resuming talks on migration, drug trafficking and postal services.
But those discussions ended after December 2009 when the Cuban government arrested Gross, a contractor distributing cellphones, laptops and other communications equipment for the American government.
The Cubans made clear that they would not release Gross unless the Obama administration freed the Cuban Five, a group of Cuban intelligence officers convicted in the United States in the late 1990s of infiltrating Miami-based Cuban-American dissident groups. Celebrated in Cuba as folk heroes, Los Cinco included Gerardo Hernández, who was serving two life terms for his role in the shooting down of two planes over Cuba in 1996 flown by an exile group dropping anti-Castro leaflets.
Sen. Patrick J. Leahy, D-Vt., a former prosecutor who had studied the cases of the Cuban Five and was convinced that their trials had been botched, lobbied the president and Eric H. Holder Jr., then the attorney general, to consider trading the Cuban Five as leverage. But Leahy was told trading convicted spies for an unjustly detained contractor was unacceptable.
"Our response was, 'If that's the case, then Alan Gross will die in Cuba,'" said Tim Rieser, a top Leahy aide.
During a trip to Havana to visit Gross in prison, the senator and his wife, Marcelle, met with Adriana Pérez, the wife of Hernández, who clutched Leahy's hands, tears in her eyes, and begged them to make it possible for her to become pregnant by her husband. Leahy won approval for Hernández to try artificial insemination, and Cuban officials transported his sperm to a fertility clinic in Panama.
"I didn't ask for any quid pro quo, but I was asking for medical treatment and better accommodations for Alan Gross, and as they worked out the impregnation of this woman, suddenly his situation improved considerably," Leahy said.
Unknown to the senator, more significant change was in the works. In December 2012, just weeks after winning re-election, Obama directed advisers to determine whether he could do "something big on Cuba" during his second term. Rhodes and Zuniga, a Honduran-born Cuba expert, were charged with establishing a confidential channel with Havana.
In April 2013, the pair sent a message, bypassing diplomatic channels to avoid leaks. The Cubans agreed to talk. Starting that June, the two White House aides began sneaking out of Washington and flying to Ottawa for secret talks with the Cubans in a Canadian government office.
The Cubans came bearing gifts with a thinly veiled subtext: boxes of Cuban cigars and bottles of Havana Club rum that the Americans were barred by the embargo from bringing home and so had to leave in Ottawa.
"Someone in Canada is very well stocked," Rhodes noted ruefully.
The Americans were obsessed with secrecy, inventing cover stories even for relatives to explain their out-of-town travels. When the Cubans suggested going out for dinner after their talks, the White House aides demurred, fearful of being spotted. Secretary of State John Kerry was informed about their talks, but few beneath him were. When Kerry held his own talks with Cuba's foreign minister, Bruno Rodríguez, neither mentioned the secret channel, leaving the Americans unsure who knew what inside the Cuban government.
Members of Congress, unaware of the secret talks, in the meantime met at the White House with Obama to press for action to free Gross. Durbin suggested appealing to Pope Francis for help. Leahy, who had met Cardinal Jaime Ortega, the archbishop of Havana, in Cuba, sent a letter asking him to raise the issue with the pope and another to Cardinal Sean Patrick O'Malley of Boston.
By the time Obama met with Francis at the Vatican in March 2014, Gross and the Cuban Five were on both men's agendas, as was a broader reconciliation between the two countries. Francis followed up with letters to Obama and Castro urging a resolution, hand-delivered by Cardinal Ortega, who was quietly whisked to the White House after an appearance at Georgetown University that had been hastily arranged as a cover story for his visit. As the cardinal met with Denis R. McDonough, the White House chief of staff, on his West Wing patio along with Rhodes and Zuniga, Obama dropped by to receive the letter.
Around the same time, there was a breakthrough: Holder agreed to support commutation of the sentences of three members of the Cuban Five. (Two had already completed their sentences.) Obama gave Rhodes and Zuniga permission to negotiate their release as part of a deal.
But the details were problematic. U.S. officials did not want to appear to be trading three convicted spies for Gross, who they maintained had been unjustly imprisoned. They were helped when CIA officials, hearing about the talks, mentioned that a Cuban man who had worked for them as a spy had been sitting in a Cuban cell for nearly 20 years, and they wanted him freed. They could trade him for the Cubans while releasing Gross on humanitarian grounds.
While details of the swap came together, the Obama administration announced the release of Army Sgt. Bowe Bergdahl in return for five Taliban prisoners, drawing protests from Republicans who blasted the move. Cuban officials believed the deal proved that Obama was open to prisoner swaps, and would therefore move swiftly to seal their pending agreement.
In fact it did just the opposite. "The backlash to that was going to make it more difficult in some respects, and made it even more important that this be a bigger than just a spy swap," Rhodes recalled.
As spring turned to summer, Gross' mental state deteriorated. Friends and family feared he would die in prison. He waged an eight-day hunger strike, halting only after his mother, Evelyn, called to beg him to eat. An effort to let him see his mother, who had cancer, failed. She died in June 2014.
Gross, gaunt and hobbled by hip problems, vowed not to mark another birthday in Havana. He told friends that he fantasized about killing one of his Cuban captors and being killed in the process.
Gross' lawyer, Scott D. Gilbert, told the White House that if his client died, Obama would shoulder the blame. "We're now at the point where we're bringing my client out on the plank," Gilbert told Zuniga during a tense meeting at the White House. "If you don't deliver on this, Alan is going to die, and this whole thing will blow up in your face."
Gilbert threatened to sue Obama on the eve of the 2014 midterm elections for failing to uphold the Hostage Act of 1868, which requires the president to take all action short of war to free an American captive held unjustly by a foreign government.
Kerry sent a handwritten note of encouragement to Gross, followed by the president's letter. Gilbert delivered them in separate trips to the military hospital in Havana where he was held. He also brought cryptic updates for Gross on efforts to win his release, typed into the body of routine legal memos to avoid detection.
By then, the talks had moved beyond Gross into details about restoring diplomatic relations and reopening embassies. In September, Rhodes and Zuniga arrived at the Vatican to present the entire package to senior advisers to the pope's advisers.
"At that point, you're on the hook to the pope," Rhodes recalled. "When we walked out of the Vatican, we knew this was over. That was the moment when I kind of exhaled."
Obama understood critics would accuse him of sacrificing human rights in Cuba for his own legacy. Just days before he would make the announcement, he invited Sen. Robert Menendez, a Cuban-American Democrat from New Jersey, aboard Air Force One for an unrelated trip. Obama made no mention of the pending agreement, knowing Menendez would not approve.
But the White House clued in supportive senators like Leahy and Jeff Flake, R-Ariz., and sent them on an Air Force jet in December to collect Gross. Not long after taking off from Havana, the pilot announced they had entered American airspace. Gross stood up, thrust his arms in the air and let out a cheer. "I haven't seen a happier man," Flake recalled.
Still, it was not over. After the dramatic announcement by Obama and Castro, the two sides settled into another six months of arduous talks to work out the details - and once again, the whole thing nearly unraveled.
Roberta S. Jacobson, the assistant secretary of state for the region, led talks with Josefina Vidal, her Cuban counterpart, that were complicated by decades of grievances like financial claims and fugitives harbored by Cuba. The two sides decided to stick to matters related to opening functioning embassies.
For the Cubans, that meant finding a bank to handle their transactions. The Americans "talked to every bank we could think of," a senior State Department official said, requesting anonymity to describe private talks, but none would risk it. Finally, a small bank in Florida whose owners supported the new policy volunteered.
But Cuba refused to allow American diplomats to travel without permission, a nonstarter for the Americans. By March, the Americans worried the talks might fall apart. Tensions rose in April at the Summit of the Americas in Panama, where Castro delivered a speech whose anti-American rhetoric was "a little jarring" to some of the Americans, the State Department official said. A long, late-night meeting between Kerry and Rodríguez left the Americans again fearing collapse.
Two weeks went by without word from the Cubans. At the State Department and the White House, officials were "buzzing around, getting uptight," the State Department official said.
But then the Cubans finally agreed to allow travel without permission as long as they were notified. Not ideal, but the Americans accepted. The deal was done.
As Obama knew, critics object. "This is the embodiment of a wrongheaded policy that rewards the Castro regime's brutality at the expense of the Cuban people's right to freedom of expression and independence," Menendez said in a speech prepared for delivery on Friday.
Nonetheless, on Friday morning, around dawn, Kerry will board an Air Force plane for Havana. Dissidents will not be at the embassy flag-raising ceremony, but he will meet with them separately. It will be the first visit by an American secretary of state in 70 years.