Why Was Alan Gross Smuggling Satellite Phones into Cuba?

​When Alan Gross set foot on American soil for the first time in five years last month, he was 100 lbs lighter, had five fewer teeth, and had lost most of the sight in his right eye.

The 65-year-old husband and father of two spent the last half decade in a Cuban prison. He was finally released on December 17 as part of an historic deal to restore relations between the US and ​the island nation.

But how did a 60-year-old, non-Spanish-speaking foreign aid worker from Potomac, Maryland wind up in Cuban jail, sentenced to 15 years for "acts against the independence or the territorial integrity of the state"?

Before arriving in Cuba in early 2009, Gross had travelled the world working as a government subcontractor. According to a website manage​d by his family, he had worked to establish jobs in the West Bank and Gaza; created and introduced farming projects in Azerbaijan, Bulgaria and the West Bank; and worked with a mining operation in Pakistan to "strengthen community relations."

When he got the assignment to go to Cuba, Gross was working for Development Alternatives Inc. (DAI), one of the many private companies that work on contract for government agencies on foreign development work. DAI landed a ​$6-million contract with the United States Agency for International Development to infiltrate Cuba with "technological outreach through phone banks, satellite Internet and cell phones," according to an Associated Press review ​of the project. As a part of this project, DAI sent Gross to Cuba on a mission to "improve wireless access for small communities across Cuba, with a special emphasis on Cuba's Jewish community," according Gross's website.

Travelling under his US passport and identifying himself as a member of a Jewish humanitarian group, Gross made five trips to Cuba that year. On each trip he brought communications equipment with him: laptops, smartphones, hard drives, and satellite phones. On his fifth trip, he was arrested by Cuban authorities under suspicion of setting up illegal communication networks. In 2011, he was convicted and sentenced to 15 years in prison.

Access to internet in Cuba is very res​tricted, with only about 5 per cent of the population online, due to a combination of a lack of technical infrastructure, governme​nt restrictions, and cost. That might finally ​change, but at the time Gross was doing his work, it wasn't outside the realm of possibility for the Cuban government to see what he was doing as a threat, especially since he was covertly working for a US government agency, according to Kenya Dworkin, an associate professor of Hispanic studies at Carnegie Mellon University.

"The Cuban government had every right to consider what he was doing illegal, despite the fact it is a terrible regime and offers its citizenry virtually no access to the internet," Dworkin said to me in an email.

"Cuba has a 5 percent internet penetration rate, and the bandwidth there is terrible. In addition, access outside of an official workplace or embassy costs about $10 dollars an hour, and the average salary in Cuba is between $20-$30 dollars a month, not enough to pay for access."

Gross and his supporters painted his i​mprisonment as the result of a naive aid worker getting duped into illegal operations to further a political operation.

"Without warnings or guidance from USAID, Gross had no reason to believe that raising the ire of the Cuban government would have any consequences beyond his deportation," wrote Stephen B. Ka​plitt, a former special assistant at USAID and a consultant to the law firm that represents Gross. But the pr​oject records show Gross expressed an awareness of the riskiness of the work he was doing, writing comments like "we are all 'playing with fire,'" and "detection of satellite signals will be catastrophic."

Larry Press, a professor of information systems at California State University, Dominguez Hills, researches internet access in Cuba and other countries. He has consulted for USAID—among other government, industrial, and non-government organizations. Press said it was highly unlikely that Gross thought what he was doing would be considered kosher by the Cuban government.

"He was not a naive guy. He'd worked on other projects like this before. He knew what he was doing was not allowed in Cuba," Press said on the phone. "I think he probably thought 'well, if they catch me they'll take the equipment and kick me out.' I don't think he thought he'd end up with that jail sentence."

But, whether he knew it or not, was the work Gross was doing illegal?

Press said the type and amount of equipment Gross was bringing into the country would not have had a big enough impact on the community to actually pose a threat, but the Cuban government has long feared the possible repercussions of an open internet.

"When they first came on the internet in 1996, there was high-level debate over how to deal with the internet. They were really scared by the way information becoming pretty much free in the Soviet Union had brought the Soviet Union down," he said. "That fear persists today."

It could explain why Cuba made such a dramatic example of Gross for bringing in a few laptops and satellite phones.

"Cuba has a very different side to the story than the United States in terms of what his activities there were," explained Scott Morgenstern, a political science professor at the University of Pittsburgh and the director of the Center for Latin American Studies.

"[Gross] says it was more of a humanitarian mission to provide access and they say it was used for dissident groups to be involved in spying and things. Maybe we'll find out more information now, but both sides make a pretty good argument about what he was doing."

I asked USAID to provide more details as to what exactly Gross was doing in Cuba, but was told they "just won't have the time" to answer my questions. Instead, USAID's press officer offered me a blanket statement describing the agency's ongoing efforts to "support civil society, human rights, and development in Cuba as our two countries forge a new relationship."

But USAID's efforts in Cuba have raised eyebrows in the past, like when government documents rev​ealed secret plans to create a fake Cuban Twitter and manipulate Havana's hip-hop scene in an attempt to "spark a youth movement against the government."

After denying my request, USAID's press secretary suggested I contact DAI instead. So I did.

But nobody at DAI would answer my questions, either. Its press secretary told me: "In the course of time, Alan himself may choose to discuss his work, but at this point DAI will not be making any statements beyond what we have said on our website and elsewhere."

The statement on DAI's website comes from the company's president and CEO, James Boomgard and reads, simply: "This is a joyful day. We are delighted by the release and safe return of Alan Gross, and immensely happy for him and his family."

Gross himself, upon returning to the US, asked not to be contacted by the media.

"I ask that you respect my wishes for complete and total privacy. Claro?" he said at a press conference, using the Spanish word for "is that clear?"

As Morgenstern pointed out, the US and Cuba are two countries who have a long history of spying on one another. Though the decision to restore relations is a positive step towards healing old wounds, it won't change things overnight.

"We've seen in the past couple of years through WikiLeaks and all kinds of things that we spy on our friends and our friends spy on us," he said.

"So a country that we've had a long term difficult relationship with? It's not going to be the perfect flowering of a new relationship."