The restoration of US relations with the Castro regime is seen by many as a triumph for Barack Obama. The story of how it happened is extraordinary

Obama and Raúl Castro thank pope for breakthrough in US-Cuba relations Read more

Behind the faded doors of what once ranked among the grandest diplomatic buildings in Washington, a team of craftsmen have flown in from Havana to quietly restore the old Cuban embassy to its former glory.



Empty for two decades after the revolution and occupied since then by a “Cuban interests” section that is officially part of the Swiss embassy, the mission has been frozen in a cold war time warp as rigid and unforgiving as its government’s relationship with the US.

Ceiling fans, dark wood panels and the even darker coffee served to guests suggest hints of Havana. Yet the 110-year-old mansion on 16th Street flies no flag and its half-dozen Cuban diplomats are not even allowed US bank accounts, receiving only cash from home and rumoured surveillance from the Americans.

But Cuba is coming in from the cold. After this month’s historic meeting with President Raúl Castro in Panama, Barack Obama’s decision to remove the communist government from a US list of state sponsors of terrorism has dismantled the final barrier to normalising relations, clearing the way to finish a secret deal that was first announced to incredulous international onlookers in December.

To the shock, too, of some of those who work there, a rapid thaw in diplomatic relations could soon see the Washington embassy’s formal reopening – and by the look of the refurbished Ernest Hemingway bar, dusted-down chandeliers and polished new ballroom floor, it will be quite a party.

Yet as the dust settles from these tumultuous few months and both countries look forward to an opening up of trade and tourism that could transform both Cuba and the reputation of the US in Latin America, several mysteries remain.



Why now, after so many years of false starts? How did negotiations that appeared deadlocked over US demands for the unconditional release of Cuba’s prisoner Alan Gross get resolved? Who persuaded two countries that once brought the world to the brink of nuclear war to trust each other again?

Partial answers began to emerge, largely from American sources, in December. There were glimpses of backroom pressure from Pope Francis and secret meetings in Canada, but little sense of how it all fit together, particularly as many tracks were made in parallel by participants sometimes unaware of each other’s progress.

Now, mounting optimism that the deal will hold has finally emboldened those involved to reveal a fuller picture, and a shift in US attitudes with far-reaching consequences.

A seminal moment

A skylight at the Cuban embassy, Washington DC

Though attention focused on the Cuban agreement to release Alan Gross from Havana, interviews conducted by the Guardian with half a dozen key players from both countries suggest the more significant concessions came first from the Americans.

It began with a phone call from Congress to the State Department, outlining one of the more bizarre requests in diplomatic history.

Tim Rieser, a senior aide to the Senate appropriations committee, wanted to know if US diplomats could help arrange for the collection of frozen sperm from a Cuban spy locked up in the desert outside Los Angeles, so it could be sent to a Panama clinic to inseminate his wife.

The spy in question, Gerardo Hernández, had been sentenced to two life terms for his role in a Miami espionage ring. His government claimed it was aimed at preventing terrorist attacks on Cuban soil, but it led to him being convicted of conspiracy to commit murder after the shooting down of two planes operated by a Cuban-American group that Hernández had infiltrated.

The “Cuban Five”, as the spies were quickly dubbed, were better known than Alan Gross – a State Department subcontractor who was imprisoned after he was caught supplying telecommunications equipment to groups in Havana – and their treatment was a major source of grievance long before Gross became a US cause célèbre.

During a peace-making trip to Cuba with his wife in February 2013, US senator Patrick Leahy – Rieser’s boss and a longtime advocate of rapprochement – was approached by Hernández’s 44-year-old wife, Adriana Pérez, with a very personal plea. Pérez was worried that she and her husband would never be able to have children if he stayed in US prison much longer.

A sympathetic Leahy saw a chance to turn a humanitarian gesture into something that could also help improve prison conditions for Gross, who had severe health problems, and the senator asked his aide to raise the matter with US officials.

Senator Leahy was trying to improve the way both governments dealt with each other Tim Rieser

“I asked the Bureau of Prisons about artificial insemination, and they were able to tell me that there was at least one case they were aware of when that had been done,” recalls Rieser, whose earlier suggestion of a conjugal visit was rejected.



“I didn’t get into the logistics. My job was to find out if there was precedent for this and to encourage the State Department and the Justice Department to explore it, knowing that it could potentially help Alan at a time when Senator Leahy was trying to improve the way both governments dealt with each other.”

Washington’s willingness to help, an unusual step that – after one failed attempt – eventually led to the birth of baby Gema Hernández, was the first clue that within a year US officials would be prepared to drastically relax their view of the prisoners still further.

“The breakthrough, in my view, was in April of 2014, when key officials in the administration for the first time agreed that not only did the Cuban Five issue need to be addressed, but that commutation of the Cuban Five sentences was appropriate and would be supported,” says Scott Gilbert, lawyer for Alan Gross.

“If there is a watershed moment, this was it, because I knew there was no possibility of a deal being done otherwise.”

Tim Rieser agrees: “Had we not been able to show [the administration] and help them recognise that the cases of the Cuban Five were flawed – that they had already served 17 years and some resolution of those cases was necessary to get Alan Gross out and to get to a new policy – if Senator Leahy hadn’t convinced them of that, then we would not be where we are today.”

Cuban sources also confirm that Leahy’s early move to ease prisoner conditions was seen in Havana as a vital first step in restoring trust.

Without doubt, it helped pave the way for the next stage: secret talks that began soon afterwards in Ottawa.

‘Very businesslike discussions’

Deputy national security adviser Ben Rhodes is a trusted confidant of President Obama. Photograph: Darren Mccollester/Getty Images

The pair of White House officials dispatched in June 2013 to meet the Cubans in the relatively neutral territory of a ceremonial building in the Canadian capital were nonetheless still viewed with suspicion.

The more senior of the two, deputy national security adviser and Obama confidant Ben Rhodes, brought credibility: proof of a direct channel back to the Oval Office.

But the other, Ricardo Zúñiga, the national security council’s senior director for western hemisphere affairs, had a more troubling background, as far as some Cubans were concerned.

Born in Honduras to a family of prominent conservatives, Zúñiga had spent time in Havana as a human rights specialist at the US diplomatic mission and was suspected of attempts to undermine the regime.

“Zúñiga is a traveling salesman, distributing the most backward, anti-Cuban ideas wherever he lands,” wrote the state-run newspaper Granma when he was put in charge of White House relations with the country in 2012.

Despite this legacy, Zúñiga’s expertise gradually helped win respect, and the secret group made steady, if slow, progress at the start of what proved to be seven meetings in total, including one in Toronto.

“These were very businesslike discussions,” says one White House official. “They were not invective-filled. We had very different points of view and talked about our differences very openly … We tried to keep this as pragmatic as we could.”

It helped that neither the US State Department nor the Cuban foreign ministry, let alone anyone outside government, was aware of just what a major reset of US policy in the region was being attempted.



“These were off the beaten path in areas that the Canadian government helped set up in a discreet location away from public eye,” adds the White House official. “We wanted to do something that was going to remove this as a point of friction in our relationship with the Americas.”

By December 2013, in what was the only sign of progress visible to the outside world, Obama and Castro acknowledged their newfound respect by shaking at hands at Nelson Mandela’s funeral in Soweto.

Yet something was still missing. Those close to him say Obama was keen to do a deal but did not feel compelled, or sure it would survive an inevitable assault from Congress.

Two men helped change that: the Pope and Alan Gross.

‘The pope and the president spoke at length’

The Vatican had long been keen to help restore Cuba to the international fold, particularly since the inauguration of reform-minded Argentinian pontiff Pope Francis in March 2013.

Ahead of a planned meeting with Obama a year later in Rome, it was far from clear that the issue of Cuba was going to come up, however.

Boston cardinal Seán Patrick O’Malley, once a contender for the papacy himself and a close ally of Francis, had been asked to recommend suggested discussion topics for the Vatican to raise with Obama. He is said to have confided later that Cuba was not initially on his list.

But several sympathetic Americans believed that support from the Vatican could be vital in helping Obama overcome political resistance and persuaded O’Malley to write a second memo to the pope suggesting he bring it up.

One of these supporters was Tim Phillips, a Boston-based expert in conflict resolution who had been holding meetings with with Cuban Americans in Florida that gave him confidence change was possible.

“There was a shift going on in Miami,” says Phillips, whose group, Beyond Conflict, arranged for local community leaders to meet speakers from South Africa and East Germany who shared their experiences of reconciliation.

The older generation was passing away. There was a new generation who don’t have that same anger and attachment Tim Phillips

“The older generation was passing away. There was a new generation who weren’t born in Cuba who don’t have that same anger and attachment. Later generations of Cuban exiles came for economic, not political reasons, so they had a different mindset.”

Briefed on this by Philips and encouraged by a letter via Rieser from Senator Leahy, Cardinal O’Malley succeeded in getting the issue on to the Pope’s agenda for Obama.

“That was actually a really important meeting,” confirms a White House official. “We knew in general terms that the pope was supportive of an effort along these lines. At that meeting, the president was able to say we were trying to do something. The pope and the president spoke at length for most of an hour; it was a broad-ranging conversation, but Cuba featured heavily.”

After further letters of encouragement from the Pope, an even more significant meeting was hosted by the Vatican in October 2014, for the two delegations to finalise the deal they had been hammering out in Canada.

“The contrast between Ottawa and Rome was pretty remarkable,” adds the administration official. “When we did this meeting at the Vatican, there were portraits of past popes all around us. It was very ornate. It felt like history.”

‘Alan became an involuntary catalyst’

Alan Gross, alongside his wife Judy, speaks at a press conference after being released by Cuba. Photograph: Saul Loeb/AFP/Getty Images

Cuba frees American prisoner Alan Gross Read more

Though theories differ on the relative contributions of Pope Francis and Alan Gross, there was no doubt that when Obama returned to Washington there was a newfound urgency and a recognition that the US had to give something up if it wanted to secure the release of the increasingly unwell State Department contractor.

The change of heart by the White House was also driven by deepening concern about whether Gross would survive much longer in captivity, especially after he went on hunger strike in 2014.

“Everyone was keenly aware that Alan had vowed he would not see his 66th birthday in 2015. This created a limited time window in which to get a deal done,” says Gilbert.

“Alan’s perspective, which was quite rational, was that he had served five years of a 15-year sentence and had no objective basis to believe he wasn’t going to have to serve the remaining 10, which he was unwilling to do.”

A decision by worried Cuban authorities to move Gross to a military hospital only worsened the problem, according to his US supporters.

He lost more than 110lbs in captivity, suffered from hip problems that made it difficult to walk or stand up, had a problem with his eyes and lost five teeth from suspected nutrition issues.

Everyone was keenly aware that Alan had vowed he would not see his 66th birthday in 2015 Scott Gilbert

Gross’s arrest had helped choke off earlier progress in talks with the Obama administration. And yet without the prospect of a prisoner exchange to drive negotiations forward, it is possible that Cuba and the US may never have resolved their differences.

“Alan [Gross] became an involuntary catalyst in the decision to change the policy,” concludes Rieser. “It was clear the Cubans were using Alan Gross as a bargaining chip for their own prisoners. And like it or not, we had to face that.”

Those who secured his release believe the key was indeed a recognition from Washington that it could no longer simply make demands on Cuba; it needed to offer the country’s communist leadership a way to evolve with dignity.

“This has probably been the most dysfunctional relationship between two states in world history: the level of emotional and historical baggage borne by both countries is staggering,” concludes Gilbert.

“I first sat down with the Cubans nearly four years ago and asked them to identify the one key thing they wanted from the United States, and they immediately said ‘respect’.”

The successful conclusion to one of the Cold War’s most intractable stand-offs suggests they finally got it.

The US-Cuba thaw: a timeline