For Alan Gross Imprisoned in Cuba, Suit Against U.S. Is Part of New Strategy MEXICO CITY - Alan Gross, a computer expert with extensive experience overseas, went to Cuba in 2009 as part of a State Department program delivering satellite Internet equipment to Jewish groups in Havana. He was a longtime supporter of Jewish causes, and his wife, Judy, said he fell in love with Cuba, praised the contractor that hired him and enjoyed the work. Then he was arrested. And now, after nearly three years behind bars in Cuba, Mr. Gross, 63, is mostly angry, his wife says - and not just with the Cuban authorities who prosecuted him. In a lawsuit filed Nov. 16 in federal court in Washington, Mr. Gross directs his ire at the United States and at the contractor, DAI, accusing both of negligence for sending him on five semi-covert trips to Cuba without proper training, protection or even a clear sense of Cuban law. The case is part of an aggressive new strategy by the Gross family to win his release. After reorganizing their legal team to include a human rights lawyer, who has started a campaign to pressure Cuba partly through the United Nations, the Grosses sued the United States government for up to $60 million and made it clear that they do not intend to stay silent about their growing sense of disappointment with Washington. "Alan is a victim of 50 years of failed policy with Cuba," Mrs.Gross said, adding, "I don't like to shame people, but if that's what it's going to take, that's what we need to do," Scott Gilbert, one of the Gross family's lawyers, said the case could be especially damaging for the State Department and DAI if the discovery process produces more examples of unqualified and ill-prepared contractors sent to Cuba. He said the suit would draw attention to the American government's pro-democracy effort, which Mr. Gilbert described as "flawed in conception" and "completely messed up" in execution. Run chiefly by the United States Agency for International Development, the program was authorized in 1996 by the Helms-Burton Act, which tightened the Cuba trade embargo and allowed for money to be set aside for "democracy building efforts." Created to push Fidel and Raul Castro from power, the program has seen its budgets range wildly - from $3.5 million in 2000 to $45 million in 2008 and $20 million a year under President Obama. Some of that spending has been criticized. A government audit in 2006, for example, found that several groups with democracy grants made dubious purchases, including Nintendo Game Boys. Cuba considers the effort an affront to its sovereignty. Collaboration with the program has been illegal for years, prompting one group with the democracy program to try to evade detection by hiding satellite Internet equipment in boogie boards. Mr. Gross acted more openly. His wife says he registered the equipment he carried into Cuba with customs authorities, and was never told by his employer that Cuban law did not allow what he was doing.. "You could say Alan was naïve, and I'm sure he was in some way, but there was no indication that it was this serious," Mrs. Gross said. In a statement, DAI refused to comment on whether it had adequately trained Mr. Gross. "As much as we would like to address the numerous disagreements we have with the content of the complaint, the fact is that doing so will not advance the cause of bringing Alan home, which remains our highest priority," the company said in a statement. The State Department also declined to comment. Mr. Gross did appear to learn over time that he was engaged in sensitive activities. After his first visit working with DAI in the spring of 2009, he wrote a memo that said the group he met with "has specific concerns about government informants and the highest level of discretion is warranted." By his third trip in June, he had become more blunt, writing to DAI that "this is very risky business in no uncertain terms." Detection of the networks he set up, he said, could lead his Cuban contacts to be arrested. The lawsuit argues that these memos should have been enough to lead to additional training for Mr. Gross, or a new approach. Instead, the complaint says, DAI and the American government "failed to take an action to protect Mr. Gross." On his next trip, he was arrested. On the Friday in December when he was supposed to come home, Mrs. Gross had set the table for the Sabbath with wine and candles. She discovered what had happened only after frantic calls to the State Department, which confirmed Mr. Gross's detention.