Alan Gross was languishing in prison in Cuba when he sued the federal government for allegedly failing to prepare him for his dangerous mission on the communist island.
Gross is now free, part of a historic deal brokered by the Obama administration last year to warm relations with Cuba. But his suit has gone nowhere, blocked by a law that protects the U.S. government when things go wrong overseas.
On Monday, the Supreme Court dealt the final blow, declining to hear the case.
Observers said Gross had been up against settled law that protects the government from liability for injuries suffered by its workers overseas.
The justices did not explain their decision, which is not unusual. The high court had all but sealed the lawsuit's fate more than a decade ago, when it ruled in a different case that the government cannot be held accountable for injuries people suffer abroad.
"I don't think it's a surprise" that the court declined to hear the case, said William R. Casto, a law professor at Texas Tech University. He said the justices were unlikely to revisit the previous ruling.
Scott Gilbert, Gross' attorney, said he was "disappointed although not surprised" by the announcement. The Justice Department did not respond to requests for comment.
Gross, who grew up in Baltimore, attended the University of Maryland and lived in Potomac, went to Cuba as a subcontractor for the U.S. Agency for International Development in 2009 to help members of the island's small Jewish community connect to the Internet. He made several trips, attracting increasing suspicion from the Cuban government, but said in his lawsuit he was pushed to keep going.
On his fifth trip to Cuba, Gross was arrested, imprisoned and convicted of crimes against the state. His health deteriorated, and advocates said last year that his health had deteriorated and he was losing hope.
But In December, after Gross had spent five years in Cuban custody, the White House made the surprise announcement that he would be coming home. The United States released three Cuban agents convicted of espionage, and President Barack Obama announced plans to reestablish diplomatic relations with Cuba and open an embassy in Havana.
Gross appeared in front of reporters hours after he landed at Joint Base Andrews and heaped praise on the officials who helped secure his release.
At the same time, he was locked in a legal battle with the government.
Gross and his wife sued the government and a USAID contractor in 2012 for what they said was a failure to train him properly.
The contractor reached a confidential settlement with the couple, and Gross received a $3.2 million payout in December from the government as part of a separate settlement with the contractor. But the government successfully got the larger court case thrown out.
Some judges once allowed plaintiffs who had suffered an injury overseas to advance if they could show that the actions that led the injury took place in the United States, according to Karl J. Protil Jr., a Potomac attorney who handles cases against the government.
But the Supreme Court squelched the so-called headquarters doctrine in 2004. The case was brought by a Mexican physician whom the Drug Enforcement Administration arranged to have kidnapped and brought to trial in the United States for his alleged part in the killing of a DEA agent.
The justices ruled that if the injury happened outside the United States — even if the plan was hatched in the United States — the government could not be held liable.
All manner of cases could be "repackaged as headquarters claims based on a failure to train, a failure to warn, the offering of bad advice, or the adoption of a negligent policy," Justice David Souter wrote for the court.
The law "bars all claims based on any injury suffered in a foreign country," Souter wrote.
Gross' attorneys argued that some of the harm he faced from being imprisoned happened solely in the United States and that his suit should go forward for that reason. The courts were not convinced.
Protil said such an argument was a stretch — but understandable.
"You try to make the best argument you can with the facts," he said.
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Casto said the law has the benefit of clarity, but it leaves people sent on foreign missions few ways to sue the government if something goes wrong.
Before the ruling, Gross' attorneys argued that if the courts declined their case, judges risked giving the government another way to avoid being held legally responsible for what happens to a "U.S. citizen [it sends] into a foreign country to accomplish U.S. Government objectives in what the United States knows to be a dangerous fashion."
A district court ruled against Gross, and the Circuit Court of Appeals for the District of Columbia upheld the decision.
"Insofar as the Grosses seek to highlight the inequity in denying redress to individuals sent to foreign countries at the behest of the United States," Judge Judith W. Rogers wrote for the court, "their policy argument is better directed to Congress."
The Associated Press contributed to this story