Our Man in Havana

The Imprisonment of Alan Gross and the U.S. Effort to Bring Him Home

Alan Gross arrives at Joint Base Andrews, Maryland, December 17, 2014. Lawrence Jackson / Courtesy Reuters

The streets had darkened in Havana on December 3, 2009, as Alan Gross sat in his room at the Hotel Presidente, an elegant building located near the Cuban Foreign Ministry. It was 10 PM, and he had just gotten off the phone with his wife; they planned to have dinner together at their home in suburban Maryland the next day, when he was expected to return. Suddenly, Gross heard a loud knock at his door. Voices barked from the hallway, but Gross, who did not speak Spanish, did not understand. He opened the door and discovered four hulking security agents. Soon he was taken downstairs and forced into a compact car. He was under arrest. 

On the campaign trail in 2008 and during his first few months in office, President Barack Obama expressed his desire for a "new beginning with Cuba." Yet with Obama set to begin his second term, the relationship between the two countries remains largely unchanged. The single biggest reason for the status quo, according to the White House, is the dispute about Gross, who is still in Cuba serving the remainder of a 15-year prison sentence. Officials in Havana say that Gross was working for the U.S. government and trying to subvert the state. But from the beginning of the saga, the State Department has said that Gross was merely bringing better Internet access to Cuba's Jewish community. Speaking to a House committee in February, Secretary of State Hillary Clinton was adamant that Washington would not reward Havana for its "deplorable" conduct: "We've made no deals, we've offered no concessions, and we don't intend to do so." 

That might be true, but more than a dozen interviews with former U.S. officials, foreign diplomats, and other observers reveal that there has indeed been a U.S. government-led effort to bring Gross home. From the start, the talks have been mired in mistrust and miscalculation; each side seemed to be waiting for the other to blink. Eventually, however, the United States

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