The leader of the U.S. delegation to this week’s talks on normalizing relations with Cuba has a reputation for determination and expertise at the State Department, where she flouted custom with an unlikely rise from rank-and-file civil servant to a role that’s been described as “horse trader of the Americas.”
Diplomats and Latin America specialists describe Roberta Jacobson as a hard-charging stateswoman who tempers a steely professionalism with humor and warmth. As the assistant secretary of state for Western Hemisphere affairs, she oversees 10,000 personnel in 30 countries, is the first woman to hold the job and was the State Department’s first regional deputy assistant secretary to have risen to that rank without first being a foreign service officer.
Across the board, diplomats described her ascent to assistant secretary from the civil service, not the more specialized foreign service, as “exceedingly rare” and “practically unheard-of.”
Her tough yet sunny disposition, they say, has served her well in other regional talks on thorny topics such as trade agreements, human rights and security partnerships. But Cuba is a minefield, and Jacobson will be taking the United States’ first, ginger steps toward normalization after a freeze of more than 50 years.
“In diplomacy, there is not one right speed of doing this,” said David Jacobson, no relation, a former diplomat who worked closely with the assistant secretary when he served as U.S. ambassador to Canada and in other State Department posts. “There are times when you need to be understanding and listen, and times when you need to be crystal clear about the position of the United States. I’ve seen Roberta in both roles. She’s as good as we’ve got.”
Jacobson and her team will arrive in Havana on Wednesday for several days of talks with Cuban counterparts, the first since President Barack Obama announced Dec. 17 that the two countries would restore diplomatic relations, which were cut in 1961. The meetings were scheduled long before the policy shift was announced; for years lower-level U.S. and Cuban officials have met to discuss a migration accord. But dispatching someone as high-ranking as Jacobson – the first assistant secretary to visit in recent memory – is a sign of the Obama administration’s seriousness about changing course on Cuba.
The so-called “Cuban thaw” is a result of back-channel negotiations by the White House that were so closely held that even Jacobson wasn’t privy to the details in the beginning, ostensibly to shield her from congressional questioning had the secret dealings been leaked, according to officials with knowledge of the process. She later received briefings on the progress, but she wasn’t part of the negotiations.
Jacobson was, however, intimately involved in the case of Alan Gross, an American the Cubans had held for five years on accusations of spying and then released Dec. 17 in a prisoner swap that was key to Obama’s decision to re-establish relations. One friend recalled Jacobson’s anguish after she’d visited Gross in prison, and Secretary of State John Kerry mentioned Gross in a statement he issued in response to a request for comment on Jacobson.
“She gets a lot done out of the limelight,” Kerry said. “I think about the big hug Alan Gross gave her. This was someone who knew Roberta fought for him and delivered for him. She gets the personal piece of diplomacy instinctively. She’ll be absolutely central in these talks with the Cubans as we set the stage for the next phase in our relationship and for big opportunities in the hemisphere.”
Conflicts over Cuba
The freeing of Gross and, later, 53 political prisoners whose release the United States had sought, has done nothing to mute the protests in Congress from members who see the normalization of relations as providing a tyrannical, untrustworthy regime with the opportunity to consolidate power and repress opposition.
A taste of what’s likely to lie ahead was in evidence at Jacobson’s confirmation hearing before the Senate Foreign Relations Committee in November 2011. There, some of Congress’ most outspoken Cuba critics, including Sens. Robert Menendez, D-N.J., and Marco Rubio, R-Fla., complained that more relaxed U.S. policies toward Cuba had resulted in trips featuring salsa dancing, cigar factory tours and baseball games at a time when the Castro government had increased its targeting of political activists. How, they demanded, did softening the U.S. stance on Cuba make any sense?
“Senator,” Jacobson replied to Menendez, “our goal in changing the regulations was to and is to expand the ability of average Cubans to have contact with Americans, not through their government – to have people-to-people contact. In doing so, we certainly recognize that there may be economic benefits to the regime, but we believe that they will be outweighed by the benefits to individual Cubans of having that greater access to information and to Americans.”
She maintained that position last month at a news briefing where she was asked about some lawmakers’ vows to block funding for a U.S. embassy in Havana. “U.S. embassies are not a gift to countries,” she said. Among consular and other functions, an embassy also can keep close watch on regimes accused of human rights crackdowns, she said.
Tom Shannon, a State Department counselor and a former assistant secretary for the Western Hemisphere, noted that Jacobson had handled difficult negotiations before. He recalled that as deputy assistant secretary for North America, Jacobson worked on the Merida Initiative, a U.S.-Mexican partnership to fight organized crime. She not only delivered “a tremendous work of diplomacy with the Mexicans,” he said, but also handled the financial and programming logistics and kept Congress in the loop.
The trickiest challenge now, he said, will be the diplomacy with the Cuban government itself, which hardly shares the U.S. goal of fostering a political opening through new warmer ties.
“That’s something the Cubans didn’t envision as a purpose of normalization,” Shannon said.
Anti-Castro activists will closely follow the degree to which Cuba’s human rights record factors into the normalization discussions. At her news briefing, Jacobson said human rights were always on the agenda at the migration talks but she made it clear that the issue wasn’t expected to derail the new diplomatic initiative.
“I do think that some human rights issues will be talked about in this trip,” she said. “I do not necessarily think that we’re talking about direct human-rights conditionality in the restoration of diplomatic relations part.”
Perhaps the most significant step the Obama administration can take without congressional approval would be removing Cuba from the U.S. list of state sponsors of terrorism; it’s been a fixture since 1982. Jacobson played it safe in her answer to that question at the briefing, calling such a step “a hypothetical that I’m not sure I know all of the implications of.”
But she didn’t rule it out, either, and she acknowledged that a review of the listing was underway to determine whether the label still fit based on criteria such as whether Cuba had participated in or supported acts of terrorism in recent months and whether the government has renounced the use of terrorism.
Obama has asked for recommendations from the review within six months. Jacobson hinted that the process might wrap much sooner, saying that “one can always turn the professor’s work in early if you want to make a good impression on the professor.”
Mark Entwistle, a Canadian diplomat-turned-consultant who’s worked on Cuba for two decades, including four years as Ottawa’s ambassador in Havana, called the terrorism list a “very big issue for the Cubans,” but also an impediment to the U.S. side’s ability to widen the dialogue.
“It would be hard to have a fulsome conversation about having a more normal relationship when there’s an overhang of a treatment that’s not very normal,” said Entwistle, who’s known Jacobson for years because of their overlapping diplomatic portfolios. “Roberta may even start doing some of this next week.”
A profile of Jacobson in the alumni magazine of Brown University, her alma mater, describes how government service wasn’t always her dream job. She’d grown up in suburban New Jersey with hopes of becoming a dancer, according to the magazine. She performed and was stage manager for many theater productions during her time at Brown.
After deciding that she “just wasn’t good enough” to dance professionally, as she put it in the magazine interview, she applied to the Fletcher School of Law and Diplomacy at Tufts and then embarked on a career in government.
Fascinated by what she described in the article as Latin America’s emerging “laboratory of democracy,” Jacobson would spend the next 25 years focused on the region.
The photos on Jacobson’s Twitter accounts suggest a woman who enjoys her job. She was photographed in Ecuador, posing before elegant architecture with a caption in Spanish saying she was “delighted with the beauty” of a historic quarter. In other shots, she’s beaming among a group of Peace Corps volunteers in Mexico and touring a World Cup soccer stadium in Brazil.
In 2012, a little fun on the sidelines of her work caused Jacobson some grief, though her friends thought it more comical than scandalous. It all began when then-Secretary of State Hillary Clinton showed up at Jacobson’s birthday party in the Colombian resort town of Cartagena, where the U.S. officials were attending a 34-nation Latin American summit.
The two diplomats were seen dancing and socializing – with Clinton knocking back a beer – in photos that ran in major newspapers and went viral in foreign-policy circles. Supporters saw nothing wrong with hardworking officials enjoying a night on the town with friends. Detractors deemed the conduct unprofessional.
Much of the criticism centered on the locale for Jacobson’s birthday party, which might not sound as controversial these days. She celebrated at a Cuba-themed nightclub called Café Havana.
Kevin G. Hall and Tish Wells contributed to this article.