An in-depth look at Alan Gross’ time in Cuban prison

Alan Gross is almost out of hope.
November 5, 2014

UPDATE [Dec. 17, 2014]: ” target=”_blank”>BringAlanHome.org. His wife, Judy, said in a September interview that her husband is now so despondent about ever being freed that he’s “passively wasting away,” refusing visitors and also the care packages they could bring.

“I try to get him to change [his attitude], but I don’t have any evidence for him to say, ‘This is how it’s going to change,’ ” Judy Gross said. “There’s no evidence that anything is happening.”

Anti-Castro hardliners like New Jersey Democratic Sen. Robert Menendez — who chairs the Senate Foreign Relations Committee — and Florida Republican Sen. Marco Rubio — who sits on that committee — oppose any trade for Gross and demand that Cuba release him unconditionally on humanitarian grounds. The odds of the Cubans doing so appear slim.

Instead, it appears Cuba’s government, as indicated by its inaction and according to multiple analysts and experts who spoke with the Journal, is prepared to let Gross die unless Cuba gets something in return for his freedom. 

If Gross sticks to his pledge to not spend his 66th birthday in captivity, his only hope of returning home alive lies with the Obama administration, which now has less than seven months to decide whether to take responsibility for a civilian contractor its own State Department sent to Cuba unprepared. 

Gross’ future also relies, to some extent, on a network of relatives, rabbis, synagogues and Jewish groups who are (and some who aren’t) pressing Washington to secure his release, as well as on the government officials that so far appear to be doing nothing to free him.

The clock is officially ticking on the life of Alan Gross, and Cuba has made clear what Washington will have to give if it wants him back. The question now is: Will the Obama administration make a deal?

A pawn in a geopolitical game

As a technology expert and international development specialist with experience working in places like Azerbaijan, Bulgaria and Gaza, Gross had brought Internet and technological consulting to remote communities across the world for 25 years before his trips to Cuba in 2009. In Cuba, however, unlike on previous jobs,  Gross was required to lie and say he was working on behalf of a Jewish humanitarian group, according to an investigative report by Associated Press correspondent Desmond Butler. 

Cuban authorities arrested Gross in his Havana hotel on Dec. 3, 2009, the ninth day of his trip, just moments after he ended a phone call with his wife, Judy, who since the arrest has led a furious effort to pressure Havana and now Washington to resolve the crisis and bring her husband home. Gross was jailed first in the notorious Villa Marista prison in Havana. One month later, he was moved to a maximum security unit in a military hospital, where he was held for 14 months, until the government, after a two-day trial with no jury and four judges, convicted him of subversion and sentenced him to 15 years in prison. 

Since 1959, when the communist revolution on this island just 90 miles off Florida’s coast brought to power Fidel Castro’s totalitarian, anti-American regime, relations between the two countries have been toxic, with the U.S. government enforcing a trade embargo and orchestrating — with the help of Cuban exiles in Florida — several covert missions aimed at toppling the Cuban government and assassinating Castro.

Alan and Judy Gross with their daughters, Nina and Shira. Gross family photo

Cuba, for its part, has been a serial violator of human rights; Fidel and his brother Raúl have run it as a police state, and for two weeks in 1962, brought the United States and the Soviet Union to the brink of war when Fidel briefly convinced the Russians to house nuclear missiles on the island. 

Cuba’s government also continues to enjoy close relations with many American adversaries, including Russia, Iran, Venezuela and North Korea.

According to Gross’ trip reports obtained by the Associated Press, USAID had tasked him with setting up uncensored (and thus illegal) Internet connections for Cuban Jews. To the Cubans, this type of democracy-promotion mission run by USAID is akin to acts of espionage.  

Gross was not an obvious choice for the mission: He was a late-middle-aged technology expert, a humanitarian and a family man doing a risky job in a hostile country that ought to have required someone fluent in Spanish, which Gross was not, and experienced in covert — or at least discreet — fieldwork, which he also was not. 

In fact, it appears Gross received little, if any, training from USAID before traveling to Cuba carrying specialized mobile phone chips, SIM cards, satellite phones, wireless access points and large quantities of other modern information devices that, as Gross said in a May 2012 interview with CNN’s Wolf Blitzer, could be bought in any Best Buy in America but are seen as a threat to state security in Cuba.

So now, Gross’ fate rests with a Cuban government that is vindictive yet fishing for a deal and a U.S. State Department that to date has shown no willingness to negotiate. Working, too, against Gross’ fortunes is a portion of the Cuban émigré population in the U.S. and Cuban-American politicians in Washington who oppose any normalization of relations or negotiation with the Castro regime. So far, the Obama administration has been unwilling, perhaps because of pressure from those groups, to offer the only deal that might bring Gross home — which would be to trade his freedom for one or more of three Cuban spies (the remaining members of the infamous Cuban Five) who were arrested in Florida in 1998 and have been convicted and imprisoned in the U.S. for espionage.

‘He’s passively taking his life’

Whenever Gross, on his trips for development projects, arrived in a new city with a Jewish community, one of his first destinations was always a local synagogue. “In his previous life he was a Jewish organizer and very active in the Jewish community,” Judy Gross said.

Rabbi Jack Luxemburg of Temple Beth Ami, a suburban Maryland congregation, recalled that when the Grosses were members there, Alan helped establish its first band and “played a mean mandolin.”

“He’s a very talented man, very soulful, very devoted to the Jewish people, to Jewish values,” Luxemburg said.

Allowed regular telephone access from his Havana prison, Gross speaks with Judy several times each week, and occasionally with key Jewish leaders in Washington and New York who advocate on his behalf.

Ronald Halber, executive director of the Jewish Community Relations Council of Greater Washington (JCRC), is one of Gross’ strongest advocates. He has helped organize petition drives drawing signatures from more than 10,000 people, led vigils outside a Cuban government office in Washington and met with State Department officials to discuss Gross’ imprisonment. He said he also has spoken with Gross numerous times on the phone.

“Sometimes I’ll read him the sports column about the Redskins or about the Nationals,” Halber said. “Usually we are talking about efforts to get him out.”

For months, Gross held out hope that the declining health of his mother, who died in Texas in June after a battle with lung cancer, would persuade Cuban authorities to let him go for a visit (he promised to return to prison). The Castro government refused both that request and a subsequent one to attend her funeral. 

Because of his mental state and his poor health, Gross has discouraged both of his daughters (Nina, 27, and Shira, 30) from visiting. Nevertheless in July, Nina, who lives in Oregon, went with her mother to Havana for three days to see her father for the first time in more than four years.

“That was very, very tough emotionally for everybody, to see the two of them so happy together and then to see them have to say goodbye … not knowing if you’re going to see each other again,” Judy said. “Imagine that — hugging your father and sobbing.”

A spokesperson in the office of Gross’ attorney, Scott Gilbert, said that Gross has “strongly discouraged” a visit from Shira, who since her father was arrested was diagnosed with and underwent successful treatment for cancer.

When Judy visits, Cuban authorities allow the couple to spend a day in a home outside of Havana, where they can enjoy a measure of privacy and a fresh meal, notwithstanding the ever-present ear of the government. “We know they are still listening,” Judy said. “There’s a guard outside of every door.”

Aside from that fleeting respite, Gross lives in a 12-by-12-foot room for 23 hours a day, along with two Cuban inmates. His daily diet, Judy said, consists of a “gooey egg” for breakfast, and rice, beans and chicken for other meals — fruit and vegetables are a rare luxury. “He’s lost so much weight. It’s not very appetizing food,” she said. “A couple of times there have been little things crawling in his food, so he doesn’t eat all the time.”

Judy used to send him care packages filled with books, magazines and healthy food through the U.S. Interests Section in Havana. Earlier this year, though, Gross began to refuse visitors as a sign of his disgust with the U.S. government for not negotiating his release; before that, he went on a hunger strike to protest his detention and “the lack of any reasonable or valid effort to resolve this shameful ordeal,” as he said in the statement released by his family in April.

“He goes through all kinds of emotions, from feeling very, very distraught; very, very pessimistic; hopeless; angry,” Judy said. 

Although media reports and Gross’ self-imposed May 2015 deadline suggest that he may be suicidal, Judy said her husband is simply losing the will to live and is  “passively taking his life.”

A ‘trusting fool’ or James Bond?

After Congress passed the Helms-Burton Act in 1996, which authorized the State Department to fund programs and missions aimed to weaken the Castro regime, Havana’s government declared the law illegal, meaning anyone in Cuba operating under the Helms-Burton banner became a state threat.

The Cuban government, due to its justified paranoia that the U.S. is always working to undermine its hold on Cuban society, considers even civilian USAID contractors to be in the same category as spies. Stephen Kaplitt, a former USAID attorney and State Department adviser, wrote in a December 2013 piece in Politico that he was “stunned” when he learned that the State Department had sent Gross to a hostile country to perform discreet work viewed by the Cubans as subversion.

“The simple act of plugging in a modem [in Cuba] suddenly becomes ‘imperialist aggression,’ ” Kaplitt wrote in Politico. “None of this was explained to Gross before he accepted his assignment.” At worst, Kaplitt said, Gross believed he could be deported if caught, certainly not imprisoned on charges of espionage and sedition.

While Gross’ own notes, which he took after each of his trips to Cuba, indicate that he had become increasingly aware of the “risky business” of setting up Wi-Fi there, the State Department appears to have concealed from him its own goal: to advance the collapse of the Castro regime. 

Asked for comment, a State Department spokesperson declined to answer specific questions but maintained that Gross’ release “remains a top priority of the United States.” 

Gross’ notes further indicate that he enlisted the help of other American Jews on mission trips to transport his large amount of communications equipment in small increments — had he carried one large bundle of high-tech devices, it would have more quickly tipped off Cuban customs agents. His own notes suggest he may not be quite the “trusting fool” he said he was at his trial in 2011, but he was also no James Bond or Jason Bourne.

Robert David Booth, a former State Department special agent and deputy director for the Office of Counterintelligence from 1996 until 2002, wrote to the Journal in an email that Cuba’s intelligence service is so suspicious of visiting Americans that it will monitor their “every activity” and keep tabs on them “from the moment a U.S. citizen visitor leaves the airport.”

Booth, who is releasing a book in December about his counterintelligence experience during 28 years of service, believes that whoever signed off on Gross’ mission “seemed to have been dismissive of Castro’s paranoia of most things American and the Cuban intelligence service’s mission and capabilities.”

Why won’t Washington act?

Senior Cuban foreign affairs official Josefina Vidal has said publicly her government would, without preconditions, negotiate Gross’ prison sentence. The U.S. would in turn have to discuss the fate of the so-called Cuban Five, three of whom have remained imprisoned in the U.S. since their arrest in 1998. They were charged with espionage and conspiracy to commit murder; two completed their sentences and returned to Cuba as heroes. The remaining three — all serving life terms — are a cause célèbre in Cuba. 

U.S. government officials, though, refuse to negotiate for Gross’ release. The irony is that although Gross is not actually a spy, it might have helped his case if he had been, as Washington may have been more likely to trade one of its own clandestine agents for the three Cubans.

A State Department official who requested anonymity seemed to imply as much in an email to the Jewish Journal, saying that Gross’ imprisonment is “not comparable” to that of the Cuban Five, even though “Cuban government interlocutors frequently attempt to compare” the two situations.

Professor Arturo Lopez-Levy, an expert on Latin America and a visiting scholar at Mills College in Oakland, believes that although the Cuban regime doesn’t want Gross to die in prison, it will let him if the U.S. continues to refuse to negotiate. “They will not release him unilaterally,” said Lopez-Levy, a Cuban Jew who worked as a political analyst for the Castro regime before immigrating to the United States, via Israel, in 2001. 

“You send somebody to create intimate networks circumventing the control of the government, you can say all you want about access to Internet, but if your policy is regime change, you cannot expect the Cuban government to say, ‘Oh this is only for people to read news and so people will read about Jennifer Lopez and Marc Anthony,’ ” Lopez-Levy said. 

Gross’ wife and Gilbert, his attorney, have of late focused most of their energy, without success, on attempting to push the U.S. government to deal with the Castro regime.

“To be blunt, we are getting nothing out of the State Department,” Judy Gross said. “The Cubans offered quite a long time ago to sit down and negotiate, so we ask what’s happening with that, and their answer is, ‘We are working on it.’ ” 

Washington-area Jewish activists, who for four years held a weekly vigil outside the Cuban Interests Section, also have begun to refocus their efforts from the Cuban government to their own. According to Rabbi Arnold Saltzman, a congregational rabbi in Maryland and JCRC board member who spoke with Gross in early September, the vigil’s leaders decided to temporarily suspend the gatherings out of concern that further demonstrations could endanger the regime’s current willingness to trade Gross.

Richard Shore, an attorney in Gilbert’s office working on Gross’ case, said that he’s working now to “press the Obama administration — to have the U.S. engage and to obtain a directive from the president to bring Alan Gross home.”

A deal for Gross has broad support in the Senate, where in November 2013, 66 senators signed a letter urging the president “to act expeditiously to take whatever steps are in the national interest to obtain his release.”

One week earlier, on Nov. 15, an opposing group of 14 senators led by Menendez and Rubio urged Obama to work “for Alan Gross’ immediate and unconditional release,” rejecting their colleagues’ willingness and the Cuban demand to negotiate a deal.

Together those two letters beg the question: If the White House likely would enjoy enough Senate support for negotiating with Cuba for Gross’ release, why hasn’t it done so?

Separately, the groundwork for détente already has been laid. Most policymakers, and certainly this White House, see little value in continuing to isolate Cuba in the hope that doing so will bring democracy and an open market to the island. A survey taken in January by the Atlantic Council, a nonpartisan think tank, similarly found that 75 percent of Americans “would like the United States to hold meetings with Cuban officials on issues of mutual concern.” 

But one important, and very loud, voice to the contrary is based in Florida, home to about 70 percent of this nation’s Cuban-American population, or 1.2 million Cuban ex-pats and their U.S.-born children and grandchildren. Florida is also a key swing state in many presidential elections, and though the state’s Cuban-American voters historically have voted overwhelmingly for Republican presidential candidates, Barack Obama — who won the state in 2012 by 73,000 votes, a less-than-1-percent margin — nearly split the Cuban vote with Republican candidate Mitt Romney. That split was viewed by some as a possible indicator of a seismic electoral shift.

Recent data also suggests that Florida’s Cuban-American community, most of which has historically opposed a thaw with the Cuban regime, may be open to a less adversarial relationship. 

“The Cuban-American community is not a monolith,” said Jose Azel, a senior researcher at the University of Miami’s Institute for Cuban and Cuban-American Studies. Asked whether Cuban-Americans animated by anti-Castro politics have influenced the White House’s refusal to negotiate for Gross, Azel was ambiguous, but said the administration “should be using every tool in our diplomatic and pressure apparatus to get him released.” For Azel, though, one diplomatic tool that Obama should not employ is the carrot of returning Cuba’s three spies.

“That should never happen,” Azel said. “That’s not a comparable situation.” 

But the desire to pressure Havana for Gross’ freedom — without compromise — among the majority of the Cuban-American community and its elected officials, is, according to journalist Jeffrey Goldberg, a primary reason the State Department won’t negotiate.

“There’s a hardcore [group] of people who are opposed to any kind of normalization of relations with Cuba,” said Goldberg, a national correspondent for The Atlantic who has traveled frequently to Cuba and has met with Fidel Castro as well as with leaders of Cuba’s Jewish community. “The administration lives in fear of them.”

Most, if not all, attempts by Washington to loosen Cuban travel and trade restrictions have been met with fierce resistance by Washington’s Cuban-American politicians. Talks in any form with Cuban officials remain a political third rail.

When in 2011 the Obama administration unilaterally liberalized some U.S. travel to Cuba, allowing students and religious and cultural groups to visit the island, Florida politicians including Republican U.S. Rep. Ileana Ros-Lehtinen, who was born in Havana and moved to Miami at 7, objected, saying it would do nothing to advance democracy and could financially bolster the regime. 

Democratic Senator Robert Menendez, a Cuban-American,  characterized Obama’s move as providing an “economic lifeline to the Castro regime” and, along with Ros-Lehtinen, Republican Rubio, Texas Republican and Cuban-American Ted Cruz and 10 other senators also signed the letter pressuring Obama to continue the current policy of demanding that Cuba unconditionally release Gross.

The views of the anti-normalization crowd, though, in addition to not being shared by most Americans, may no longer even be held by many Cuban-Americans. A June poll by Florida International University revealed that among 1,000 randomly selected Cuban-Americans living in Miami, respondents were nearly split when asked whether the U.S. should continue its trade embargo. A similar poll in 1991 had found 87 percent of Cuban-Americans supported the embargo.

The American public’s new willingness to engage with Cuba would be good news for Gross if the White House took it as a cue that it could politically survive a deal with the Castro regime. For critics of Washington’s policy of Cuban isolation, though, that the administration won’t negotiate indicates a lingering fear of political blowback.

“Everyone talks about the Jewish lobby,” Goldberg said. “Just wait until you see the power of the Cuban lobby.”

The view from the East Coast

The campaigns pile up: There’s the 2013 letter from 66 senators, another one signed by 300 rabbis and a campaign launched in September that has received more than 11,000 signatures on a letter to be sent directly to White House Chief of Staff Denis McDonough, pleading for Obama to negotiate for Gross’ freedom. 

Rabbi Steve Gutow is president and CEO of the Jewish Council for Public Affairs (JCPA). With offices in Washington, D.C., and New York, JCPA is the nation’s foremost Jewish communal public affairs group and is leading the current letter campaign for the plea to Obama. In a September interview, Gutow spoke with care when asked if he feels the government could do more to bring Gross home.

“I do, without specifics,” Gutow said. “If they felt differently, they should respond, ‘Look we are doing more than you can imagine.’ Respond to us; respond to Congress.”

It’s not as if Washington never trades prisoners with authoritarian regimes. One recent example is the deal Washington struck for Sgt. Bowe Bergdahl — with the Taliban. Bergdahl, an American soldier, went missing in Afghanistan in 2009 and in May, the Obama administration traded five Taliban prisoners held in Guantanamo Bay for his freedom, even though Bergdahl is now being investigated by the U.S. Army for allegedly deserting his post — a criminal offense.

Fred Burton, vice president of intelligence for Stratfor, a global intelligence and advisory firm based in Austin, Texas, was a special agent at the State Department from 1985 to 1999. Burton said in an Oct. 24 interview that backchannel negotiations for prisoner swaps happen frequently, even if “the media and the public [don’t] see.”

“The [State] Department goes out of their way to say, ‘We don’t negotiate,’ ” Burton said. “But in many ways this would be the kind of agenda item that we would always raise behind the scenes.” 

The American Jews who visit Havana

From Dec. 4 to 7, The Jewish Federation of Greater Los Angeles will bring 30 local community members to Cuba on a mission to help provide the island’s tiny Jewish community with religious items, some kosher food and basic over-the-counter medication that is hard to come by there.

It will be the third such trip to Cuba for the L.A. Federation in the past six years, and it is only one of many that Jewish groups across the United States go on — synagogues and Federations regularly bring Jews to Cuba to supply prayer books, kosher food, religious items, Tylenol and sterilized medical needles, which are used for diabetics and are in short supply there. Traveling under the auspices of a humanitarian mission also provides the legal loophole allowed under U.S. law that permits Americans to see Cuba — or at least a sanitized version of it.

Adela Dworin, the president of Cuba’s Jewish community, said in an Oct. 22 telephone interview from Havana that in the winter, when Americans can best tolerate Cuba’s weather, she regularly meets with visiting American-Jewish delegations — sometimes several per day — who bring Chanukah materials and other goods.

Stanley Falkenstein, who lives in Los Angeles, created the Jewish Cuba Connection in 2000; he travels alone regularly to the island with supplies and some cash to support the community there.

“They reuse the needles because they are just hard to get, so I’ll bring down a thousand needles, and I’ll bring them to a doctor,” Falkenstein said, adding that Jewish groups that come in the winter bring so much of the same supplies that Havana’s Jews “probably have enough Tylenol to kill every headache in Central and South America” and “enough siddurim to probably take care of everybody in Israel.”

Falkenstein said one reason he travels in person is because he assumes the Cuban government monitors its citizens’ telephone and email communications.

“All their communications are read and listened into,” Falkenstein said. “That’s why I go, because I can email, and you get these answers that seem to go in circles. They are nervous, and I don’t blame them.”

He said that when he raised the case of Alan Gross to Dworin, she just looked at him and remained silent. “When they look at you,” Falkenstein said, “It means they don’t want to answer.”

For Cuba’s Jewish community, Gross is not and cannot become a political issue — the small Jewish population has a peaceful relationship with its own government, and agitating on behalf of Gross could endanger that. Asked about the American contractor, Dworin said that Cuba’s Jews had never asked for the work he was providing.

“I don’t know why he came to Cuba,” Dworin said, speaking in a heavy Cuban accent. “The Jewish community doesn’t need his sophisticated equipment, because we are a small community, and we can communicate with the rest of the communities in the island, and we also can call to other countries. We can travel [and] have been in Israel.” Havana’s main synagogue, the Patronato, has Internet that community members can use, but, Dworin said, using the Internet at home in Cuba is difficult and very expensive; most Internet users rely on cybercafes.

In the U.S., how Jewish mission trips should approach Gross’ ordeal is a matter of debate. Jay Sanderson, president and CEO of the L.A. Jewish Federation, said in an interview that the L.A. Federation’s Cuba missions “do not connect to Alan Gross in any way” and that “the only place [Jewish organizations] can make an impact is in Washington — not in Havana.”

“What would we do? Would we walk around [in Cuba] with signs saying, ‘Free Alan Gross’?” Sanderson said. “I’m not being dispassionate. I’m just being realistic, and this is something that we have clearly talked about in the Federation system.” 

The Journal also asked spokespeople at the American Jewish Joint Distribution Committee and B’nai Brith International — both of which have major aid programs for the Jews of Cuba — as well as at UJA-Federation of New York, the Jewish Community Center of Chicago and the Washington, D.C., JCC — all of which confirmed that Gross’ plight is not a planned topic of discussion on any of their Cuban mission trips.

Not unexpectedly, though, some of Gross’ advocates, most obviously his wife, feel that leaders of Jewish missions going to Cuba have an obligation to educate their members about Gross’ imprisonment. Judy Gross believes every group of American Jews traveling to Cuba “needs to know” about her husband and that trip leaders should ensure that their groups “discuss it every time” among themselves — not in order to agitate Cuban officials, but just to raise awareness among American Jews.

“Absolutely, absolutely,” she said. “When I hear about a group going, I make it my business to tell them about it.”

Rabbi Luxemburg of the Gross family’s former synagogue said efforts to free Gross should be understood in the context of the Hebrew phrase “matir asurim,” which Jews cite three times daily in prayer services, and refers to God as the redeemer of captives. “We call God ‘matir asurim’; God is the one who frees the imprisoned,” Luxemburg said. “I think this is a godly thing for us to be doing — to engage in any and all efforts to bring Alan home.”

The JCRC’s Halber, one of Gross’ most vocal and unrelenting supporters, believes the task of the American Jewish community is to pressure the Obama administration, publicly and privately, to make a deal regardless of the political fallout, and to understand that the president “is the only one, in the end, who can bring Alan Gross home.”

Recalling a recent telephone call with Gross that helped clarify how those fighting for his freedom and life can continue fighting, despite coming up empty for nearly five years, Halber said that when he told Gross how sad he felt about his situation, the American prisoner in Havana responded:

“Don’t get sad — get mad.”



Changes were made to an earlier version of this article to reflect that needles delivered by humanitarian groups to Cuba are for diabetics. In addition, the Jewish Cuba Connection was created in 2000, not 2010.

Did you enjoy this article?
You'll love our roundtable.

Editor's Picks

Latest Articles

More news and opinions than at a
Shabbat dinner, right in your inbox.

More news and opinions than at a Shabbat dinner, right in your inbox.

More news and opinions than at a Shabbat dinner, right in your inbox.