What Alan Gross Was Doing in Cuba

Why was a government contractor from Potomac in a Cuban jail, anyway?
Alan Gross arrives at Joint Base Andrews on Wednesday. Photo by Lawrence Jackson, via the White House.

When Alan Gross landed in Havana in early 2009, he looked the part of someone arriving on a tourist visa: cargo pants, loose cotton shirt, Rockport shoes. He usually traveled with Jewish humanitarian groups. He did not identify himself as an agent of the US government.

Gross was in Cuba on behalf of Development Alternatives, Inc. (DAI), an international development contractor in Bethesda. DAI in turn had a $28.3 million contract with the US Agency for International Development to finance communication systems for faith-based groups in Cuba.

On Wednesday, Cuba agreed to release Gross from prison, where he’s been held for the past five years. This is the story of how he got there.

On his first trip, Gross brought in enough equipment to set up the first of three systems for wi-fi hotspots that could provide unrestricted Internet access for Cuban Jews. He carried his telecommunications equipment in backpacks and carry-on bags.

Gross, who graduated from Virginia Commonwealth University with a masters degree in social work, had worked in international development for years—he helped farmers in emerging countries market their goods, worked with small businesses in the Middle East, and helped get a school built in Pakistan.

In 2001 he formed the Joint Business Development Center, a firm focused on setting up information and communication systems in developing countries. He eventually built and managed approximately 150 Internet-access points in remote areas of the world.

Gross’s kits typically contained modems that could access satellites, as well as laptops and cell phones. He called them “telco in a bag.” His contracts, some with USAID, took him to Europe, Ukraine, Israel, Gaza, Afghanistan, Iraq, and other parts of the world.

He seemed perfectly suited for the USAID job. In addition to his experience setting up communications systems in other countries, he had traveled to Cuba, had worked on USAID contracts and had experience with DAI. He would set up satellite communications systems for Cuba’s Jewish community of about 1,500. He wanted to help Cuban Jews connect with the rest of the world, Judy Gross says; he would also make an estimated $500,000. He signed on as a subcontractor to DAI in February 2009.

Gross was aware that the US and Cuba had strained relations, and the Communist government maintained strict control over its citizens. But since he was working on a USAID contract, Judy says, he figured he was safe.

“I don’t think he understood how much risk he was at, initially,” says Professor William LeoGrande, a Cuban expert at American University.

That was, to say the least, naive. “The Cubans don’t have a live-and-let-live policy about anything, much less a US government agent installing communications equipment,” says Phillip Peters, a Cuban expert and former State Department official who writes the Cuban Triangle blog. “Going to Cuba is not like going to Connecticut.”

According to trip reports obtained by the Associated Press and made public in a subsequent lawsuit, Gross asked members of Jewish humanitarian groups to pack some of the equipment and bring it through customs.

Gross submitted detailed plans to DAI, which approved every aspect of the project, down to each cell phone and Internet installation.

There were signs Gross knew he might have been bringing in sophisticated equipment that would raise suspicions. On one occasion, he arrived with three Broadband Global Area Network devices, or BGANs. BGANs use a satellite signal to connect computers or phones to the Internet. Gross wrote in one of his trip reports that he hoped to throw off Cuban authorities by placing tape over their brand names.

Gross knew he was veering close to spycraft, but USAID is not supposed to be in the business of running clandestine operations.

By email, USAID spokesman Matt Herrick told Washingtonian earlier this year: “In non-permissive environments, the fact that our efforts might not be welcome, does not make them illegal, and discreet does not equal covert.”

In fact, USAID has veered from helping farmers market their crops to subverting elected governments. USAID’s Office of Transition Initiatives funds and trains political protest groups who actively work with opposition leaders against regimes that the US wants to change. The Associated Press reported earlier this year that USAID built a social media service called ZunZuneo with the goal of undermining the Cuban government (it vanished in 2012; the agency took the unusual step of rebutting AP’s story with a listicle). Another operation recruited Cuban hip-hop artists.

After one or two trips, Gross started to see he might be in jeopardy.

“This is very risky business in no uncertain terms,” he wrote in one trip report to DAI. “Provincial authorities are apparently very strict when it comes to unauthorized use of phone frequencies . . . Detection usually means confiscation and arrest of users.”

In September 2009, between his fourth and final trips to Cuba, USAID summoned Alan Gross to its headquarters in the Reagan Building to report on his work in Cuba. In a PowerPoint presentation, he talked about the risks he had encountered. Neither agency officials or DAI representatives commented, according to his wife, Judy Gross.

At home in Potomac after his fourth trip, he told Judy he thought he was being followed.

But he returned to Cuba. On Thursday, December 3, Cuban authorities showed up at Gross’s hotel and arrested him. It was about an hour after he’d phoned Judy to say he was wrapping up his fifth trip and would see her the next day. He was convicted of crimes against the state and sentenced to 15 years in prison.

Did Alan Gross know that he might be breaking Cuban law by bringing in the equipment and setting up communications systems?

“Alan was a risk-taker,” says Judy, “but he trusted everybody. I guess you could call that naive.”

Alan Gross sued the US government and DAI in federal court for $60 million in November 2012. He charged DAI with “gross negligence” for sending him on covert missions without proper training. In an affadavit filed in March 2013, he alleged that the US was negligent as well, and said he was never “aware or warned that activities contemplated by this USAID and DAI-sponsored project were crimes in Cuba.”

In the same document he allowed: “I certainly was aware of the strained and often difficult relations between the US and Cuban Governments since 1950.”

Documents filed in the lawsuit surfaced some shoddy and embarrassing aspects of USAID’s and the State Department’s programs in Cuba. Gross wrote trip memos “warning of the riskiness of his covert work and the perils if he got caught,” according to court documents. The reports were shared with USAID.

US District Judge James Boasberg dismissed the lawsuit against the US because the government “retains immunity for injuries suffered in foreign countries.” But he added that the court is “in no way condoning what happened to Gross or implying he is to blame.”

Boasberg declined to dismiss Gross’s case against DAI. In May, 2013, DAI agreed to a secret settlement with Gross and paid the family an undisclosed sum.

USAID administrator Rajiv Shah was not with the agency when it approved the contract with DAI that wound up sending Gross to a Cuban prison. (Shah announced Wednesday he would step down as head of USAID next February.)

Shah, 41, has had little to say in public about Alan Gross. According to Herrick, Shah “met in person” with Judy Gross. She and her lawyers say the meeting never happened.

For four years after Gross was convicted, the US government took the position that he was unfairly detained. It refused to negotiate and called for his unconditional release. Gross lived in a hospital prison cell with two Cubans. He lost 100 pounds. One of his teeth fell out. While he was imprisoned, his mother died. The Cubans had denied his request to see her before she passed away.

Meanwhile, Judy Gross had to go it alone. She moved out of their home in Montgomery County and found an apartment in DC. With attorney Scott Gilbert, she lobbied for her husband’s release. Both visited Gross in Cuba, as did several members of Congress.

The State Department began negotiating in secret with Cuban officials earlier this year. The Cubans demanded that the US release three of their nationals who were convicted of spying in 1998 in exchange for Gross’s freedom. With the help of the Vatican, the US and Cuba agreed to swap prisoners.

On December 17, President Obama announced Gross had been freed and that the United States planned to normalize relations with Cuba.

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