For the past four years, U.S. Agency for International Development contractor Alan Gross has wasted away in a Cuban prison, serving a 15-year sentence for providing Internet access to the island’s small Jewish community.

He’s counting on lawyer Scott Gilbert to win his freedom and bring him home to Washington.

Gilbert is an unlikely choice of counsel. The founding partner of 30-lawyer Gilbert LLP is not a human rights specialist or an expert in international law. Rather, he’s best known as a hard-charging insurance recovery litigator with an eight-figure book of business and a penchant for motorcycles.

As he works furiously to win Gross’ freedom, Gilbert is confident the diplomatic knot ensnaring his client is just another variation of the complex disputes that he’s spent his career untangling — albeit one where a man’s liberty, and perhaps his life, hang in the balance.

“Of all the commitments I’ve made to clients in 35 years, I’ve yet to fail on one. This will not be the first,” he said of his pro bono work for Gross, which now occupies 30 to 70 percent of his time each week. “It’s true, I’m not a human rights lawyer. But my specialty is the resolution of complex, multiparty disputes, developing strategies and then implementing them effectively. … This is effectively the same thing.”

Gilbert had made four trips to Cuba in the past year to see Gross — visits he describes as “surreal.” Machine-gun toting guards wearing berets line the hallways of a military hospital where Gross is now imprisoned. He spends 23 hours a day in a 10- by 12-foot cell with two other prisoners, and has lost 110 pounds. Gilbert has been allowed to meet with Gross in a small, windowless room with cinderblock walls and four chairs for anywhere from two to eight hours, he said.

Gross, now 64, was pulled from his hotel room in Cuba in the middle of the night and arrested on Dec. 3, 2009. He was working as a subcontractor for Bethesda, Md.-based Development Alt­ernatives Inc., which had won a $28 million contract from the Agency for Inter­national Development, part of a wider effort to promote democracy in Cuba.

Gross’ task was to train members of the island nation’s Jewish community on the use of mobile phones, wireless technologies and personal computers as a means of “breaking down barriers to Cuban citizens’ access to information,” according to the company’s request for proposal.

Former Secretary of State Hillary Clinton said in a 2012 interview with CNN that he was not a spy. “Mr. Gross was not an intelligence agent,” she said. “Mr. Gross worked for a development group that was helping Cubans, principally in their small Jewish community in Cuba, to have access to the Internet.”

Gross was arrested on his fifth trip to Cuba and held for 14 months without charges. In March 2011, he was tried and sentenced to 15 years in prison for “acts against the independence or territorial integrity of the state” for providing the communications equipment — precisely what he was hired to do under his contract. Under Cuban law, it’s illegal to distribute communications systems that are not under government control.

“He tries so hard to hold on to hope, but it is fading fast,” Gross’ wife Judy said at a Dec. 3 rally in front of the White House. “I do not know how he does it, and I don’t know how much longer he will go on.” Gross’ family members at home are struggling as well — his mother has terminal lung cancer and his daughter is fighting breast cancer.

‘THIS NIGHTMARE’

Gilbert was brought into the case in 2011 by Williams & Connolly, which was representing Gross and his wife and continues to be involved in the matter. Gilbert works frequently with lawyers from the firm on insurance matters, and initially, his role was to sue Development Alternatives, as well as the contractor’s insurance company and the Agency for International Development in U.S. District Court for the District of Columbia — work that was done on a special fee basis.

Gilbert and firm lawyers Barry Buchman, Ivan Snyder and Emily Grim alleged the company and the U.S. government were negligent, failing in their “duty to take basic remedial measures to protect Mr. Gross based on [their] superior knowledge” of the dangers he faced in Cuba.

The case against Development Altern­atives settled for an undisclosed sum in May. The suit against the government was dismissed that same month by U.S. District Judge James Boasberg, who found that the Federal Tort Claims Act protected the United States against claims “arising in a foreign country.” The ruling is on appeal.

As Gilbert came to know Gross and his wife — and to consider them close friends — his role in their representation expanded as well. It now encompasses all aspects of the case, work which the firm volunteered to perform pro bono.

It’s a far cry from his usual caseload representing companies suing their insurers — his firm has helped clients recover more than $40 billion from their carriers. Gilbert is particularly known as the chief negotiator and author of the Wellington Agreement, one of the largest insurance settlements in U.S. history that resolved insurance coverage disputes among 34 asbestos producers and 16 insurers.

Over the years, he’s cut a wide swath in the Washington legal community. A martial arts black belt who favors jeans and cowboy boots and drives race cars for fun, he got his start at one of the city’s most traditional firms, Covington & Burling. He left the firm in 1997 for Dickstein Shapiro, a departure that was noisy and acrimonious — both sides had lawyers oversee the transfer of client files.

Gilbert launched his own firm in early 2001. Motorcycles are something of a trademark for him. He owns three of them, and a Ducati and a Harley Davidson are displayed in the firm’s reception area.

In recent weeks, he’s met with Cuban officials including the foreign minister, as well as rallying support within the administration and in Congress. Last month, 66 senators led by Patrick Leahy (D-Vt.) sent a letter to President Obama urging the administration to “act expeditiously and take whatever steps are in the national interest to obtain [Gross'] release.”

Partner Richard Shore and associate Natalie Baughman are also working on the matter.

“We’re trying to have the United States at the highest level engage with Cuba and negotiate a resolution,” Gilbert said, adding that the Cuban government said it is willing to “sit down without any preconditions.” However, the Obama administration has resisted any attempt to link Gross’ release to that of the so-called Cuban Five — convicted in 2001 of spying charges in Miami.

In a letter, Gross expressed his gratitude for Gilbert’s work. “Thank goodness for the leadership, hope-instilling work and information provided by my legal team,” he wrote in a letter to Obama read by his wife at the rally at the White House. But he also expressed his despair. “With the utmost respect, Mr. President, I fear that my government — the very government I was serving when I began this nightmare — has abandoned me.”

Contact Jenna Greene at jgreene@alm.com.