After arriving in Maryland on Dec. 17, 2014, Alan Gross speaks to family and friends who were awaiting his return from five years of captivity in Cuba. (U.S. Air Force/Reuters)

Although his high-profile scene in the diplomatic-relations drama starring the United States and Cuba will eventually fade to subplot, the role Alan Gross played raises critical questions about the way this country uses people to represent its interests.

If “uses” sounds a bit pejorative, that’s the point.

Among the questions his case poses: Is it appropriate for the U.S. Agency for International Development (USAID) to send people not trained in intelligence or statecraft to do secret work in repressive countries that consider those activities to be against their laws? Is that work worth the risks of imprisonment for those individuals, the credibility hit to U.S. foreign development programs and an increase in international tensions?

Gross, a USAID subcontractor, was released from a Cuban prison last week as part of a rapprochement leading to restoration of diplomatic relations following a half-century of estrangement. A Cuban court found him guilty of “acts against the independence or territorial integrity of the state” in 2009 and sentenced him to 15 years in prison. He served five.

His acts included providing information and communications gear and training to the island’s small Jewish community and others. That might sound harmless, but Cubans are well aware that the explicit policy of the U.S. government has been regime change in Havana. Cuban officials place whatever Uncle Sam does in that context. They consider any USAID activity in Cuba illegal.

Certainly, USAID officials must know that. But no one told Gross.

“After my arrest, I was informed by Cuban Government officials that it was illegal in Cuba to distribute anything funded in whole or in part by USAID,” he said in an affidavit. “At no point before or during the . . . Project was I aware or warned that activities contemplated by this USAID and DAI-sponsored project were crimes in Cuba.” DAI is Development Alternatives Inc., a commercial international development firm that was the prime contractor for Gross’s work.

Gross swore the affidavit in March 2013 as part of a lawsuit against USAID and DAI. The firm paid an undisclosed sum to settle with his family, which is appealing federal district and circuit court dismissals of the case against the government.

This isn’t the only time USAID, known for its international humanitarian and development work, has used what it calls “discreet” programs against the Cuban government. According to the Associated Press, in 2009 the agency attempted to recruit Cuban hip-hop artists to agitate against the Castro regime and formed a Cuban Twitter company, “Zun­Zuneo,” to encourage dissent.

“But discreet does not equal covert,” USAID spokesman Matt Herrick said in a blog about ZunZuneo. “Allegations that USAID has conducted or supported covert operations are baseless and false,” he added in an e-mail.

USAID did not answer specific questions about Gross, but Herrick put the responsibility for the contractor’s security on DAI. “It is the responsibility of our implementing partners,” he said, “who work in closed or repressive environments to provide USAID the necessary assurances that they have security protocols in place appropriate to operating in a closed society and will strictly employ those protocols for all professionals traveling to such environments.” DAI spokesman Steven O’Connor would not answer questions about Gross’s activities.

Despite USAID’s deflection to its contractor, this was a USAID-funded operation for a USAID project that was illegal in Cuba. “USAID approval is needed for everything. We cannot freelance,” reads one set of notes from an August 2008 meeting between the agency and DAI. The notes and some documents were posted by the nongovernmental National Security Archive.

Gross was not a spy, and Cuba was wrong to treat him like one. But he also was not a naive do-gooder. His activities were at least semi-covert and he took efforts to conceal them. Among the items in what he called a “Telco-in-a-bag” was a “discreet” subscriber identification module (SIM) card. In a September 2009 document outlining an expansion of his work, Gross said the card would “impede the ability (of Cuban government technicians) to track or detect” his equipment by “masking the signal so that its GPS location cannot [be] pinpointed to within 400km,” about 250 miles. He warned that the discovery of other equipment he provided for “usage for Internet access would be catastrophic.”

Although he didn’t think he would be arrested, which happened on his fifth trip, he feared his Cuban contacts might be because of their association with him.

“This is very risky business in no uncertain terms,” Gross wrote in a memo following his third trip. “Provincial authorities are apparently very strict when it comes to unauthorized use of radio frequencies. . . . Detection usually means confiscation of equipment and arrest of users.”

That’s what happened to Gross.

But he was warned that if caught, he was essentially on his own, according to the company’s motion to dismiss the Gross lawsuit: “With respect to this travel, the Subcontract provided that, ‘[g]iven the nature of the Cuban regime and the political sensitivity of the USAID Program, USAID and DAI cannot be held responsible for any injury or inconvenience suffered by individuals traveling to the island under USAID funding.’ ”

Five years in prison is more than an inconvenience.

Twitter: @JoeDavidsonWP

Previous columns by Joe Davidson are available at wapo.st/JoeDavidson. .