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Buzzfeed's Joshua Hersh has an incisive article looking at the case of Alan Gross, an American contractor held in detention in Cuba for years, and notes how it is an example of how American efforts to promote democracy abroad are often flawed.

The Villa Marista prison in Havana is a complex of ornate, industrial-era buildings situated on the outskirts of the city. Before Fidel Castro came to power, in 1959, it was a Catholic boys school, but today it serves as the country’s main detention center for political prisoners. A fearsome place, its cells are cramped and dank, with beds made of iron planks hanging on chains, and a filthy hole in the corner of each room for a toilet. The prison guards are known for brutal interrogations and creative acts of petty cruelty; the lights are often kept on throughout the night, and in the evening an inmate might be served his breakfast and told it is morning.

One night in early December 2009, a genial, portly 60-year-old man from Potomac, Maryland, was pulled out of his hotel room in central Havana and dumped into one of those cells. Alan Gross had arrived in Cuba a week and a half earlier on a U.S. government–backed mission to bring uncensored internet access to Jewish communities on the island, and was scheduled to fly home the following morning. He wouldn’t make it back to the U.S. for more than five years.

Gross had come to Cuba to espouse and spread the values and benefits of democracy by helping to make internet service more accessible; he had visited synagogues and Jewish leaders across the country, introducing them to search engines and Spanish-language Wikipedia. (“I saw the world,” one of his beneficiaries later reportedly said, after being shown Google Earth for the first time.) For this, he was convicted of undertaking “a subversive project” to “destroy the Revolution” in Cuba, and sentenced to 15 years in prison. U.S. officials protested strongly, characterizing Gross as a humanitarian. Last December, on the same day the Obama administration revealed plans to restore diplomatic ties with the Cubans, after nearly six decades of impasse and isolation, it announced that Gross would be coming home, too.

Aside from a few off-the-record appearances and a single interview, Gross has not spoken publicly about his experiences, and he rejected numerous attempts to be interviewed for this article. (A book deal and network television interview are believed to be in the works, and his website lists a contact for a speech agent. A $3.2 million settlement with the U.S. government, finalized late last year, came with a strict nondisclosure agreement.) But since returning to America, he has emerged as an advocate for closer U.S.–Cuban relations, and has a lively presence on Twitter, where he shares artwork he drew while in prison and observations from his recovery and reintegration into everyday life. In early June, after Republican Sen. Marco Rubio, a hard-line opponent of open relations with Cuba, threatened to block the appointment of a U.S. ambassador to the island, Gross quipped, “When will Sen Rubio recognize that significant on-the-ground changes are taking place in Cuba under his nose?” He’s even embraced the snappy tone of social media: When a critic accused him of having Stockholm syndrome, he replied swiftly, “Not a fuckin’ chance.”

Gross’ resilience is striking. Friends and others who have seen him since his return describe him as having retained his upbeat attitude and lively sense of humor. (In a phone message he left for a supporter near the end of his captivity, Gross chuckled and apologized that it “took me so long” to get in touch.) But his writings and legal documents from the five years of wrangling over his case in Cuban and American courts, and interviews with friends and colleagues, tell a story of great anguish, and occasional bewilderment. “I have never — repeat, never ever — been in any kind of trouble, legal or otherwise, anywhere in the world,” Gross noted in a handwritten statement he filed before a Cuban court in 2011. “I did nothing in Cuba that is not done on a daily basis in millions of homes and offices around the world. I have an immense fondness for the people of Cuba, and I am deeply sorry for being a trusting fool. I was duped. I was used. And my family and I have paid dearly for this.”
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