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Judy and Alan Gross's family is at heart of standoff between Washington and Cuba

By Mary Beth Sheridan
Washington Post Staff Writer
Friday, May 21, 2010; C01

It was 6 o'clock on a Friday evening, and Judy Gross knew the drill. She checked the computer and saw that her husband's plane had just landed at Dulles. Alan would be home in Potomac in 45 minutes, bursting in the door with stories from his latest trip to Cuba, she figured. She bustled around her gleaming kitchen, preparing Shabbat dinner.

But the clock hit 7, and there was no Alan. Eight, and still no Alan. She called the airline and discovered that her 60-year-old husband had not made the flight.

"So then I knew something wasn't right," Judy recalled.

She didn't panic. Like other international aid workers in Washington, Alan had had his share of mishaps on far-flung assignments -- car accidents and nasty stomach bugs. His wife asked U.S. diplomats to check the Havana hospitals.

But when the phone rang a half-hour later, Judy learned Alan wasn't sick. He was in Villa Marista, the Cuban state security prison. "I was scared," Judy stuttered, in her first in-depth media interview. "I was very scared for his safety."

That December evening marked the start of a harrowing five-month family drama and a new standoff between Washington and its Cold War nemesis. Cuban officials have publicly accused Gross of working for American intelligence agencies. The United States government denies that.

But, as details have trickled out, it appears Gross was involved in something stranger: a secretive program to foster democracy in Cuba.

The program has been around for years, using travelers posing as tourists to slip typewriter ribbons, shortwave radios and, more recently, laptop computers into Cuba. But under the George W. Bush administration, officials flush with cash sought new ways to reach out to civil society.

And that's how a klezmer-playing Maryland dad wound up providing Wikipedia to Cuban Jews.

Judy said her husband, a "gadget geek," had seemed unaware that he was courting danger when a Bethesda contractor signed him up to provide Internet access to civil-society groups on the island. "When he heard about this, he just said 'Yes!' " she recalled.

Alan P. Gross had always had an itch for adventure. Growing up in Baltimore, he'd helped out in his dad's window-cleaning business. But after marrying Judy in 1970, he earned a master's in social work and began working with Jewish groups. One of his jobs was taking local Jews on trips to Israel.

"They all loved him, of course," his wife said. People warmed to Alan's buoyancy, his sense of humor, his desire to help. "He really could solve people's problems," Judy said, sitting in her kitchen, wearing jeans and a baggy black turtleneck, a curtain of salt-and-pepper hair framing her face. The smell of blueberry muffins wafted from the oven.

Alan became entranced by travel. He moved on to projects funded by businesses, humanitarian organizations and the U.S. Agency for International Development -- assisting Palestinian dairy farmers, helping Kenya's tourism industry, introducing modern court reporting in Gambia. For weeks, he'd be away. Then he'd return toting a tribal mask or a South Asian tribal rug.

"He loved the people," Judy said. "He would come home and have stories -- he ate at this person's house, and sat on the floor, and -- just all kinds of stories. And he loved the fruit of his work."

Sometimes his two daughters would complain about sharing their father with a world far beyond their Potomac cul-de-sac.

"It was always an issue," said Judy, a psychotherapist at Suburban Hospital. "The kids would say, 'Why can't you get a normal job?' "

But a cubicle wasn't for Alan.

"He didn't want to work for The Man," said their 22-year-old daughter, Nina, grinning.

Alan didn't just have stories. He had ideas. Big ideas. Like an international peace concert on the Green Line between Israel and Gaza. That didn't work out.

He came up with a plan to keep Palestinian produce from getting stuck at Israeli checkpoints. "What was his saying?" Judy asked her daughter, and Nina broke into a smile. "When cargo flows, the economy grows!" the women chorused. That didn't get too far, either.

Alan had his dreams closer to home, too, like a machine to create fertilizer from the mountains of poultry-farm dung that threatened the Chesapeake Bay.

"I said to him once, 'Why don't you run for state Senate or something? You have all these ideas,' " Judy said. "He said absolutely not. Politics suck."

Some of Alan's entrepreneurial ideas did succeed, though. He became fixated on using technology to help poor people connect with the world. His business took off, with contracts to provide satellite Internet service to private organizations and American aid groups in Afghanistan and Iraq.

They were dangerous places. But "you're moving in a cocoon. You've got the USAID mission, you've got embassies," said Bob Otto, one of Alan's colleagues. "In Cuba you don't. . . . He might have been a little lulled."

Advancing democracy projects

In 2008, the U.S. Agency for International Development sent out a notice seeking proposals for projects to advance democracy in Cuba.

The notice reflected an ambitious plan by the Bush administration to expand Cubans' access to cellphones and the Internet, which is rationed by the communist government. U.S. officials called it breaking "the information blockade."

The administration won a 500 percent increase in funding for such projects, to $45 million. And it set out to distribute the money differently. In the past, such funds had mainly gone to democracy organizations and Cuban American groups. But some of those groups had come under fire for wasting the money on Godiva chocolates and cashmere sweaters. USAID turned to professional development contractors who would quietly provide Cuban civil-society groups with communications equipment, including satellite gear.

The agency's notice raised eyebrows. "My firm looked at it and said, whoa, this looks like someone might end up in jail," Otto said.

But Development Alternatives Inc., a Bethesda firm that does agricultural, microcredit and democracy work around the world, won a $6 million contract. The company had never worked in Cuba, according to its officials.

DAI President Jim Boomgard had known Alan Gross for years. "He was always coming around marketing: 'Here's what I'm trying this time,' " Boomgard said. Gross heard DAI was looking for Cuba ideas, and he "came forward with a proposal."

It was a half-million-dollar plan. Gross would travel as a tourist, distributing cellphones and computers to the Jewish community, and hooking people up to the Internet using small satellite devices, according to sources who did not want speak on the record about the sensitive project. Gross also helped the Cubans download music, Wikipedia and the Encyclopaedia Britannica off flash drives, they said.

Alan was more spiritual than strictly religious, his wife said. But he loved Jewish traditions and teachings. After one of his trips, he started crying as he told his wife about setting up equipment at a Cuban synagogue. "He was so happy with their reaction," Judy said.

A few weeks before his arrest, Alan met an old colleague at Tysons Corner and told him about his job. "He was the most 'up' I had seen him in quite a while," said the friend, Bob Rourke.

A question of experience

In the five months since Gross's arrest, questions about his work have arisen on Capitol Hill and among Cuba experts: They note that he apparently had no training in how to operate in a communist country.

He had traveled to Cuba five times in nine months -- a frequency sure to attract the attention of Communist authorities. Gross spoke broken Spanish he learned from Rosetta Stone software, according to family and friends. While Gross told DAI he had worked in Cuba previously, his experience there appears limited.

"The fact he would be so emboldened to go five times and not understand this is a huge red flag, is so bizarre," said one congressional staffer. Like several other government employees interviewed for this story, he was not authorized to comment on the record on the sensitive issue.

Americans involved with Cuba's tiny Jewish community are puzzled by why it was chosen for the USAID project. The community of 1,500 generally has a good relationship with the Castro government and has been allowed to receive medicine and goods from abroad, they say. Most Jewish community centers already had desktop computers and e-mail, although not Internet, they say.

"It just doesn't make sense," said June Safran, a Californian who leads the Cuba-America Jewish Mission. Now, Cuban Jews are afraid they are under heightened government scrutiny, she said. "They are worried about using e-mail," she said.

The chairmen of the U.S. Senate and House foreign affairs committees recently put a "hold" on disbursing funds for the Cuba democracy program.

"We are asking hard questions about fraud, waste and what actually works to benefit the Cuban people," Rep. Howard L. Berman (D-Calif), head of the House committee, said in a statement. "We are also deeply concerned for the safety and well-being of program participants."

Boomgard acknowledged that his firm did not train Gross on how to operate in Cuba.

"We do not generally send people to places where they're at risk of being arrested for the important work they do," he said.

However, he said Gross had received an intensive briefing and understood the risks -- at least in theory.

"While I am certain that he conceptually appreciated the worst-case scenario, he probably thought that the worst things that might actually happen are that he was turned away from the airport, or harassed and booted out of the country," Boomgard said.

Senior U.S. officials have repeatedly urged the Cuban government to release Gross on humanitarian grounds. Charles Luoma-Overstreet, a State Department spokesman, called it "a matter of grave importance to us."

U.S. officials defend the program, saying it is simply aimed at helping Cubans communicate like other people around the world. They note Gross hasn't been charged with a crime. But it is illegal under Cuban law to give or receive goods under the U.S. democracy program, or to bring in satellite equipment without a permit.

Did the program put its participants at risk?

A senior U.S. official said in an interview that "a lot of activities that are legally protected in democratic countries can be punished arbitrarily in Cuba."

As for why the Jewish community was chosen, the senior official said that "if you look at civil society groups in Cuba, there is a fairly strong religious component."

USAID said in a statement that Gross was chosen because of his "strong expertise in sustainable development approaches, experience working in difficult environments and understanding of technological approaches to strengthening civil society."

Critics say the Gross case has exposed how such secretive programs can backfire. Some lawmakers, such as Sen. John F. Kerry (D-Mass.), have urged a different approach -- like "people-to-people" exchanges worked out with the Cuban authorities. Defenders of the democracy programs say that they provide important support for dissidents and human rights activists. But even some of them have been stunned by the Gross case.

"We agree with the program, but this is rookieville," one congressional staffer said, speaking on the condition of anonymity.

A living nightmare

For Gross's family, what once seemed to be another of Alan's adventures has turned into a nightmare.

He has been allowed to call home five times.

"The first couple times he sounded really upbeat," his wife said. The third time, though, he begged Judy to send medication. Troubled by gout and ulcers, Alan began to shy away from the fried Cuban food, eating mainly fruit. He has shed 72 pounds from his 6-foot, 250-pound frame.

Judy's worst moments come when she thinks Alan may never come home.

"The problem is, the Cubans don't want to talk to us very much, or at all actually," she said. A spokesman for the Cuban Interests Section in Washington said Gross's case remains under investigation.

Cuba analysts say the most likely outcome is that Gross will be charged with a crime and then expelled.

The last time he called home, Alan seemed disoriented, Judy said.

"The thing that really struck me is, he asked me for his mother's phone number. This is somebody who calls his mother every day," Judy said.

"It was the worst I heard," she added. "He sounded very stressed and low."

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