Published at ForeignAffairs.com by R. M. Schneiderman - editor and writer for Newsweek and Daily Beast

Our Man in Havana - The Imprisonment of Alan Gross and the U.S. Effort to Bring Him Home

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 appeared to step back from an opportunity to free Gross from jail and strike a blow against the antiquated politics of the Cold War.

In the wake of Obama’s re-election, some have high hopes for Gross’ release and an improvement in U.S.-Cuba relations. But with a divided Congress peering over the fiscal cliff and preparing for other partisan battles, Cuba hardly seems to be a priority for the White House, and the United States’ long-standing embargo against the island nation—now more than 50 years old—seems as firmly in place as ever. That does not bode well for Gross.

MYSTERY MAN

Not long after Gross missed his flight, Fulton Armstrong, a senior adviser to the Senate Foreign Relations Committee, began hearing rumors that an American had been arrested in Cuba. Alarmed, Armstrong started making calls, and, little by little, he pieced together the story: Gross had been setting up satellite Internet networks for Cuban Jews—networks that the regime couldn’t control. This service was sure to anger the Cuban government, which blocks a variety of Web sites that it deems threatening. Armstrong called the State Department to confirm what he’d heard, but State denied having a relationship with Gross. Over the course of several days, the story continued to change. One State Department official erroneously told Armstrong that Gross’ mission was classified; another said that Gross likely worked for the Central Intelligence Agency.

Having spent years as a CIA officer, Armstrong doubted that Gross worked for Langley. Gross did not speak Spanish, he knew little about Cuba, and he was having meetings in places known to be crawling with Cuban agents. Lo and behold, after several weeks, the State Department finally admitted that Gross was theirs. Bit by bit, Armstrong learned that in of 2009, Gross traveled to Cuba five times to fulfill a contract worth more than $500,000 for Development Alternatives Inc. (DAI), a Maryland-based firm, which was working for the United States Agency for International Development (USAID).

Gross’ mission, approved during George W. Bush’s presidency, was part of a provocative USAID program created in 1996 by the Helms-Burton Act, which, among other things, allotted money for creating institutions and providing access to information outside of the government’s control, in hopes of quickening the fall of Fidel Castro. In an interview with CNN’s Wolf Blitzer this past May, Gross maintained that he went to Cuba simply with “some off-the-shelf equipment to test to see if it worked.” He also decided to “try to improve the computer system within the Jewish community.” Gross says he was not specifically helping dissidents. Yet working for the Helms-Burton programs is a crime on the island, and officials in Havana are especially sensitive about satellite Internet equipment; they have long memories of exploding cigars and “Yanqui invasions.” What the Cubans seemed to fear was that Gross’ project was a test mission for future operations. It’s not clear if it was, but according to a $60 million lawsuit that Judy Gross, Alan Gross’ wife, filed last month, claiming negligence against USAID and DAI, the development firm had a contract “to establish operations supporting the creation of a USAID Mission” in Cuba.

Continue reading from HOPE AND CHANGE