Four times, Alan Gross traveled to Cuba, lugging with him Internet equipment to connect the island's small Jewish community to the outside world. And four times, he completed his trips to the Caribbean island nation without a problem.
With each trip he made, the Potomac man became more concerned about his work, which defied the Cuban government's strict controls on the Internet. But at worst, he assumed, if he ran afoul of the Cuban authorities, he'd be held briefly before being kicked out of the country.
But at the end of his fifth trip, in late 2009, police seized Gross. He was charged with crimes against the state, convicted and sentenced to 15 years in prison. Wednesday marks his fifth year in custody.
For his family, Gross' incarceration has been an unending nightmare. For diplomats, it is a significant sticking point in the long-strained relationship between the United States and Cuba, the communist nation 90 miles from Florida.
Gross' supporters say his health is declining — once 254 pounds, he's lost 100 pounds since being locked up — and he's on the brink of losing hope.
"Five years is far too long for an innocent man to be locked away from his family and his country," said Gross' attorney, Scott Gilbert. "Alan is about to give up, and we are running out of time."
The State Department, members of Congress including Sen. Ben Cardin and Rep. Chris Van Hollen, and former officials including President Jimmy Carter have campaigned for Gross' release. Sens. Jeff Flake and Tom Udall traveled to Havana recently and met separately with Gross and Cuban Foreign Minister Bruno Rodriguez Parrilla, but returned empty-handed.
A spokeswoman for Van Hollen said the Montgomery County Democrat spoke with Gross by telephone in October and told him he was still pressing for his release.
"Every day that he sits in prison in Havana is another day of injustice for Alan Gross and another day that Cuba is missing an important opportunity to begin to reshape its relations with the United States," Van Hollen said in a statement.
Cuban officials have proposed a swap: the release of Gross for the return of the three members of a group known as the Cuban Five who are still imprisoned in the United States. U.S. officials have opposed the deal, saying Gross was an aid worker, while the Cuban Five were intelligence operatives who were convicted in federal court of conspiracy to commit espionage and other charges.
Gross' work in Cuba began at what Cuba watcher William LeoGrande describes as the tail end of an aggressive push by the administration of President George W. Bush to try to undermine the country's communist government.
Gross, who went to high school in Baltimore County and studied at the University of Maryland, College Park, before embarking on a career in international development, had long experience working on overseas projects to help hook up people to the Internet, according to an affidavit filed in federal court. He developed something he called a "telco in a bag" that could be used to get people online using satellites with equipment he bought at stores such as Best Buy.
In late 2008, the U.S. Agency for International Development asked a Bethesda-based contractor to develop programs to boost free Internet access in Cuba, and Gross submitted a proposal.
Gross did not speak Spanish. But he had traveled to Cuba, and he had worked on projects in dangerous parts of the world — including Iraq after the 2003 U.S.-led invasion.
He made his first trip to Cuba in March 2009. At first the work went well, he said in the affidavit — part of a lawsuit he filed against the contractor and the U.S. government — and members of the Jewish community said his equipment was superior to anything they could obtain locally.
After Gross fired up the mapping program Google Earth, a man said Gross had "showed him the world."
At the same time, Gross began to realize his work carried risks. During one trip, he said, he saw a van circling in a neighborhood where he was operating, its large whip antennas suggesting to Gross that it was sniffing for unauthorized communications.
Gross said his bosses at the contractor, Development Alternatives Inc., did not respond to his concerns and pushed him to make further visits.
In the lawsuit, Gross said USAID had used him "as a pawn in its overall Cuban policy efforts."
The company reached a confidential settlement with Gross and declined to comment on the allegations, but called on the United States and Cuba to secure his release.
Gross has remained locked up in Cuba, as one of his two daughters suffered breast cancer and underwent a double mastectomy, and as his mother died. He is being held a military hospital in Havana.
LeoGrande, a political scientist at American University and co-author of "Back Channel to Cuba: The Hidden History of Negotiations between Washington and Havana," says it looked early on as if a deal could be struck to get Gross released.
President Barack Obama had signaled an interest in improving relations with Cuba, and the government of Cuba seemed willing to let Gross out if the United States backed off some of its democracy-promotion programs on the island, LeoGrande said.
But those efforts fell apart, and Cuban officials began to tie Gross's release to the fate of the Cuban Five, who are promoted as heroes on the island.
"We've always made it clear that there's no equivalence between an international development worker imprisoned for more than four years for doing nothing more than helping Cuban citizens gain access to the Internet, and convicted Cuban intelligence agents," said Pooja Jhunjhunwala, a State Department spokeswoman.
The Cuban Interests Section, the country's diplomatic mission in Washington, did not respond to requests for comment.
The State Department says securing Gross' immediate release remains a top priority.
"We continue to use every possible diplomatic channel to press for Mr. Gross' release, repeatedly, both publicly and privately," Jhunjhunwala said. "We have also enlisted governments around the world and prominent figures to press for Mr. Gross' release."
The challenge, LeoGrande said, is that the Obama administration insists Gross did nothing wrong and should be released without any conditions.
"The administration painted itself into a corner very early," LeoGrande said. What's more, both nations' stance toward improving relations with the other is marked by deep ambivalence. Each could benefit, but each has also lived with the current arrangement for decades.
LeoGrande said the next major opportunity for progress could be at a meeting of the Organization of American States in Panama in April. Cuba might be invited to the summit for the first time, giving officials from the two countries a chance to hold talks on the sidelines.
But for Gross' supporters, that is too long to wait.
Sen. Barbara M. Mikulski, a Maryland Democrat, outlined a simple plan for Cuban President Raul Castro: "Let Alan Gross go! Let him go today, let him go now."