Sitting across from officials of the United States’ long-sworn enemy, Scott Gilbert quickly realized that in Cuba, reliable tactics he had mastered in all his years of practicing law would not be enough to secure the release of his client, a U.S. government subcontractor who’d been jailed there since 2009.
“My role was plainly that of representing Alan Gross who was an inmate in Cuba,” Gilbert told Fox News Latino. “But in this case, my strategy from the outset was to try to understand the people I was dealing with, both professionally and as people.”
In Washington, D.C., Gilbert asked Cuban officials what they most wanted from the United States.
“The answer, without hesitation, which I found so remarkable, was ‘Respect,’” Gilbert recalled. "Mutual respect and mutual trust.”
Gilbert, 61, says gaining the trust of the Raúl Castro regime, and always delivering on his word, was a key part of an extremely complex effort that reached all the way to the Vatican and Pope Francis himself, to get an increasingly depressed and ailing Gross freed from jail.
Cuba said the U.S. project Gross took part of aimed to undermine its government and sentenced him to 15 years in prison.
“I got know those officials well,” Gilbert said. “The Cubans understood that they were dealing with someone materially different from the Americans they had dealt with before. Everything I represented to them would happen, did happen.”
In December, Gross, who had been in Cuba to set up Internet access as a subcontractor for the U.S. government to promote democracy there, was released from jail and returned to the U.S. But something else that Gilbert fervently wanted to see took hold – an agreement between Cuba and the United States to restore diplomatic relations.
Gross’ freedom came with the release of three Cuban spies jailed in the U.S., the easing of trade and travel restrictions between the two countries, as well as the hope for grander steps like Cuba’s eventual removal from the State Department’s terror list and re-establishing embassies in each other's capitals.
After that, although Gilbert was, for all intents and purposes, finished with dealing with Cuba as a jailer, now he has a new relationship with the island – he is guiding its government on how to take steps to handle and attract American businesses.
Gilbert receives no payment from the Cuban government, he said.
And through Reneo, a consulting firm he launched more than a year ago, Gilbert also provides guidance to Americans who want to invest or do business in Cuba, often traveling there for these projects and reinforcing ties that he developed during the Gross case.
“Americans who have never been to Cuba think it’s just another Caribbean country,” Gilbert said. “Cuba is so different, it is never what you think.”
He says he’s long had a genuine interest in the island nation – well before he ever heard of Alan Gross two years ago. “Ironically, I’ve been a student of Cuban history and culture for a good part of my life,” said Gilbert, who resides in Florida.
He first went to the Communist nation about six years ago with B'nai B'rith on a humanitarian mission to the Jewish community in Havana.
“I was like most Americans," Gilbert recalled. "I was really surprised – based on what I’d seen and read up to that point – to discover that most of the Cuban people I met actually liked Americans.”
“The Cuban people, in Cuba and here in the United States, are an amazing group of human beings,” he told FNL. “They are unfailingly good-natured and polite and incredibly smart and strong and resolute.”
The feeling that Cuba had enormous potential that was unknown to most Americans stayed with him.
“Although much of the infrastructure is crumbling, you look past it and you can envision the future,” Gilbert said, echoing what he tells business owners who visit the island.
“It’s changed a lot” since his first visit, he says. “There’s been a lot of construction, rehabbing of some historic buildings and the number of privately-run restaurants has grown.”
He finds it maddening that U.S. business owners and investors are missing out on what he believes will be a remarkable resurgence. For now, he advises people how to do business in Cuba, and whether they can realize their goals now, or whether they should wait until the many restrictions still in place are lifted.
Many people have asked him: How does someone go from fighting Cuba, from dealing with the regime as an adversary that improperly tried and jailed his client to helping the country re-engage with the U.S.
“People ask all the time,” he said. “They say, ‘The Cuban government imprisoned your client.’” His answer is that we need “to leave behind the history, the damaged relationship."
He said the key to getting Gross out was, and to restoring ties with Cuba in ways that are beneficial both to the island and the United States still is, “trying to find where there is commonality. Finding that at bottom people are human beings – we all have aspirations, we all have families.”
As far as Gilbert is concerned very little of substance can change unless the U.S. embargo is lifted.
“The ability to travel to Cuba, to ship to Cuba – which is just 30 minutes away from U.S. shores,” he said. “But American companies are just sitting here with shackles on watching opportunities taken up by businesses in other countries.”
The embargo, he said, has been a failure in many ways.
“It’s absolutely a question of when, not if, the embargo will be lifted.”
Ric Herrero of CubaNow, an organization that supports trade and diplomacy with Cuba, lauds Gilbert's efforts to help pave the way on both sides of the Caribbean for an economic relationship.
"Paving the road for smart investments that strengthen Cuban civil society and empower entrepreneurs is exactly what our new policy is all about," Herrero said. "Achieving this will require both sides to be proactive in overcoming decades of mistrust and identifying immediate opportunities to increase socioeconomic ties between the United States and Cuba."
Herrero added, "Intermediaries who can play a constructive role in facilitating meaningful engagement during this process should be welcomed."
Recent polls show that a growing number of Americans, including those of Cuban descent, support that view. But many remain firm in their opposition to breaking bread with Cuban officials while they still refuse to implement democratic reforms and address human rights concerns.
"The almighty dollar trumps everything," said Raúl Mas, a Cuban-American who supports the embargo and whose late brother, Jorge Mas, played a pivotal role in creating the influential lobbying group, the Cuban American National Foundation. "[Gilbert] represented someone who was mistreated by the Cuban government, and now he turns around and is cahoots with the Castro brothers. It's less than dignified."
Remberto Pérez, a New Jersey businessman who is against establishing diplomatic and business relations with Cuba as long as there is no democratic reform, said the embargo was put in place originally because the Castro regime was seizing American businesses and property.
"Now we want to do business with the very same people who seized American businesses? It's the same guys in power," Pérez told FNL.
For his part, Gilbert understands that there remains a solid wall of resistance to lifting the embargo – including in Congress – and realizes that there are still enormous gulfs to be bridged.
“In many ways, we come from very different worlds,” he said, “from different countries, we have different interests. This is just three or four months out of decades of bad history between Cuba and the United States.”
He says he is focused on the nations, the people in both countries, and helping them come together and share opportunities that will be mutually beneficial.
Even Alan Gross himself, he notes, recently told reporters that he wants to the return to Cuba to "promote a more constructive relationship" between the island and the U.S.
Gross spoke at a private fundraiser at Gilbert's home earlier this month for the New Cuba PAC, which plans to back political candidates who favor increasing travel and trade between Cuba and the United States. Gilbert said he does not have an official position with the PAC, but he supports its mission.
"I believe it is an important part of a critical effort that will provide a better future for the Cuban people and will provide significant benefits to the United States, including Cuban-Americans, the rest of our citizens and our business community," he told FNL.
“If Alan Gross can move forward, so can our respective governments’ officials.”
Elizabeth Llorente is Senior Reporter for FoxNews.com, and can be reached at Elizabeth.Llorente@Foxnews.com. Follow her on Twitter @Liz_Llorente.