Reporting from Potomac, Md. — Alan Gross usually celebrates Rosh Hashanah, the Jewish new year that started at sundown Wednesday, by playing mandolin in the klezmer band that accompanies his guitar-strumming rabbi in the High Holiday service.
But this year, Gross is imprisoned in Cuba, where he has been held since Dec. 4 in a bizarre Cold War-style case that has become the latest irritant between Washington and its longtime nemesis in Havana.
State security arrested the 60-year-old amateur musician and professional aid worker at the Havana airport after he allegedly provided unauthorized satellite Internet connections to Cuba's tiny Jewish community. The Communist regime strictly controls Internet access through state-run servers, and household Internet connections are illegal.
Raul Castro, Cuba's president, accused the American of "undercover subversion," but Gross has not been formally charged. The Obama administration denies Gross is a spy, saying he worked under a U.S. Agency for International Development program mandated by Congress to promote democracy in Cuba.
The case has complicated White House attempts to ease tensions with Cuba. Plans to allow more Americans to visit or send money to families on the island nation have been repeatedly delayed, although some U.S. officials believe a new overture may help prompt Gross' release.
Gross initially was held in Havana's Villa Marista, a high-security prison often used for political prisoners, but he soon was moved to a military hospital, where conditions are less severe, according to officials familiar with the case. Tall and heavyset, he is said to have lost 80 pounds in custody.
U.S. diplomats based in Havana and a Cuban lawyer hired by Gross' family visit him regularly. He writes letters to family and friends, and is allowed to phone his wife, Judy Gross, every few weeks. He has an electric fan and may watch TV, and is treated better than other prisoners, according to officials familiar with the case but who asked for anonymity because the case is in a sensitive phase.
Family members declined interview requests, fearful that publicity may hamper U.S. and European diplomatic efforts to win Gross' release. But Judy Gross recorded an emotional video appeal in February to the Cuban government.
"Alan has done nothing wrong and we need him home," she said.
Judy Gross called her husband a "humanitarian" who has worked in more than 50 developing countries to build schools, improve local markets and develop communications systems. In post-invasion Iraq and Afghanistan, he installed scores of portable terminals that link computers to the Internet via satellite.
In Cuba, Gross worked as a subcontractor for Bethesda-based Development Alternatives Inc., which was awarded a $6.8-million USAID contract in 2008 to support "just and democratic governance" on the island.
Gross then won a DAI subcontract for $590,000 to help Jewish groups "access Wikipedia, CD versions of the Encyclopedia Britannica, things as benign as that. He was making it possible to access the Internet," said company spokesman Steven O'Connor.
Gross spoke only broken Spanish, and made five trips to Cuba in nine months, traveling with a tourist visa — a frequency Communist authorities were almost sure to notice.
Begun in 1997, the USAID program has used tourists and other visitors to sneak shortwave radios, flash drives, cellphones, fax machines and other equipment to local civic groups. Even though most of the devices are legal in Cuba, collaboration with the U.S. program is a crime punishable by up to 20 years in prison.
"The Cubans view it as a continuation of the efforts that began under the Kennedy administration to overthrow their government," said Philip Peters, a Cuba expert at the Lexington Institute, a conservative think tank in Washington. "Mr. Gross was in great danger, and he probably didn't realize it."
Christopher Sabatini, policy director at the Council of the Americas, an international business organization, said Gross acted naively. "This is a very repressive, near-police state. I'm sure he was followed every step of the way."
A report last month from the liberal Brookings Institution contended that "the covert political nature of these programs has put at risk not only U.S. operatives, but also their beneficiaries" in Cuba.
Indeed, some activists fear that Cuba's 1,500 Jews may face increased scrutiny now. Foreign visitors regularly provide the congregations with medicine, school supplies, religious materials and other goods.
"The Cuban authorities are watching more carefully all interactions between Cuban Jewry and the international community," said Rabbi Sunny Schnitzer, executive director of the Cuba-America Jewish Mission, a nonprofit group based in Berkeley. "I would say everyone is walking around on eggshells."
The regime has rebuffed repeated appeals to let Gross go home on humanitarian grounds.