Nuevo Mundo

12.18.14 10:45 AM ET

Meet America’s Next Ambassador to Cuba

Believe it or not, the United States has a man in Havana—and he's set to get a big promotion.

Resuming diplomatic relations with Cuba means a promotion for Jeffrey DeLaurentis, the career foreign-service officer currently serving as chief of mission in the U.S. interest section in Havana. He will become charge d’affaires, which confers much the same status as ambassador. Once President Obama’s critics quiet down, and concede however grudgingly that he’s acting in the country’s best interest by taking this great leap forward with Cuba, DeLaurentis could well be the president’s choice for the historic posting of a U.S. ambassador to the island nation after a 54-year hiatus.

The Senate confirmed him once before, in 2011, for a posting to the UN. And he has served in Havana twice before, once in the early ’90s, soon after beginning his career after graduating from Georgetown University School of Foreign Service, and again from 1998 to 2002. He’s a highly regarded professional, says Ted Piccone, a senior fellow at Brookings and a Latin scholar, who was in Cuba Wednesday for the simultaneous historic announcements from the presidents in Havana and Washington.

“He is exceptionally well qualified to manage this historic and positive change in relations for the foreseeable future,” Piccone said in an email that praised Obama’s actions and noted that Secretary of State John Kerry’s announcement that he intends to visit Cuba in 2015 is “another very strong sign of the deep commitment to move this agenda forward, with or without congressional support.”

Implementing Obama’s decision to normalize relations is not for the faint-hearted. “This will take a lot of solid negotiating,” says Mark Schneider of the International Crisis Group. He cited among other factors narcotics, environmental issues, and counterterrorism, areas that require the skill of a career foreign-service officer like DeLaurentis. “He’s a smart guy, very committed, always concerned about issues of democracy, and he’s very professional, level-headed. He thinks through issues.” Schneider points out that DeLaurentis has been in his post in Cuba since the summer, so he’s been in on all the pre-planning that’s gone on unbeknownst to much of Washington for some time. “He’s smart, he’s serious, he’ll do an exceptional job,” says Schneider, a former director of the Peace Corps and a veteran of many international aid and development programs.

Sarah Stephens of Democracy in the Americas, a bipartisan group that has long promoted ending the embargo with Cuba, said in an email from Havana that when DeLaurentis was first appointed as chief of mission, “he was clearly not a caretaker (and not an ideologue) but someone who could help engineer a transition in relations, and people viewed his appointment that way.”

Johanna Mendelson, who chairs the board of visitors of the Western Hemisphere Security Institute and has worked with DeLaurentis, describes him as a “measured and cautious diplomat, which means he’ll do a great job. He’s not the life of the party, let’s put it that way. But he’s certainly personable, thoughtful, and responsive. He’s businesslike.”

Republicans are threatening to withhold funding for an embassy in Cuba, but more money won’t be necessary, says Piccone. “The large U.S. Interest Section building, which is the same building that used to be the embassy, sits in a prominent spot… and is easily convertible to an embassy without any need for increased funding from Congress,” he wrote in his email.

While Obama’s announcement Wednesday caught much of official Washington by surprise, those in the know were aware that this was coming, and many were in Havana for the big day. Among them is David Dreyer, a former Clinton aide whose Twitter account describes him as a communications strategist, media trainer, and student of Latin America, especially Cuba. I asked him to describe the U.S. mission that will likely revert back to the embassy it was more than a half century ago.

This is what he wrote: “The building is an imposing structure close to the sea wall—which Cubans call ‘the Malecon’—that separates the city from the harbor.  This is where Cubans walk, couples hold hands, and classic cars drive by at night. It has also been a public space and flash point for demonstrations at hard moments in Cuba-U.S. relations.”

Dreyer recalled that during the tenure of Chief of Mission James Cason, a Bush appointee who served from 2002 to 2005, the United States installed a news ticker at the top of the building that flashed messages to Cubans walking by, ham-handed statements, according to Dreyer, that included “everything from quotes by Frank Zappa about how buying things makes you feel good, to insults about Cuban women (saying they went out with European tourists for money).”

Cason loved being provocative, says Dreyer. He once attended a Cuban trade fair, where American farmers were trying to sell beef, wearing a big button with a red line through a cow. Cason is now retired from the Foreign Service and is the mayor of Coral Gables, Florida.

When the ticker first went up, then-President Fidel Castro retaliated by installing 75 black flags on high poles to obscure the ticker and keep the U.S. propaganda from being seen by the Cuban people. Eventually both sides calmed down and the ticker delivered some real news, but it was a symbol of an era that Obama wanted to change. “One of Obama’s first moves as president was to shut the ticker down,” Dreyer wrote in his email. “It is now possible the building can be a symbol for progress.”