America's Man in Havana - R.M. Schneiderman, Foreign Affairs

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

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.
"We said, 'Look, message received,'" Armstrong told me. "'These [democracy programs] are stupid. We're cleaning them up. Just give us time, because politically we can't kill them.'"
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.

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