How Alan Gross Went From Rotting in a Cuban Jail to Enjoying the Good Life in Tel Aviv

After spending five years in a Cuban jail when he was falsely accused of being a spy, the 68-year-old former aid worker made aliyah to Israel this year. He refuses to be captive to his lost years

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Alan Gross in Tel Aviv
Alan Gross in Tel AvivCredit: Courtesy
Amir Tibon
Amir Tibon

Exactly three years ago, on December 15, 2014, Alan Gross was speaking with his wife from prison in Cuba, where he had been held captive for over 1,800 days. An American citizen who had been arrested on false charges by the Cuban authorities in 2009, Gross was about to go back to his cell when his wife, Judy, said to him, “We’ll never have to talk like this again.” At that very moment he knew he was about to be released.

Gross arrived in the United States two days later. It was a Wednesday and, coincidentally, the first day of Hanukkah. The first words Gross said as he delivered a short statement to the media were “Hag Sameah!” His release was a Hanukkah miracle for his family and friends, giving a special meaning to the Jewish festival of lights.

Three years after the end of his Cuban nightmare, Gross has now fulfilled a lifelong dream: Earlier this year, he and Judy immigrated to Israel, a country which he has “always considered home,” as he tells Haaretz during a recent visit to his old hometown of Washington.

The couple bought an apartment in north Tel Aviv, not far from the busy thoroughfare of Dizengoff Street, and Gross now spends much of his time exploring the endless variety of restaurants, cafés and fast-food joints in the area. Gross says he visited Israel “maybe 60 times” over the last four decades, adding that his decision to make aliyah was “long overdue.”

Alan Gross in Tel AvivCredit: Courtesy

During our interview, Gross, 68, talked about his time in prison, his conversations with former President Barack Obama, and his wish to help develop economic ties between Israelis and Palestinians – something he had previously worked on in the 1990s.

“My first visit to Israel was at the age of 28, leading a group of 45 teenagers on a tour of Israel as part of their summer camp. It was an incredible experience,” he recalls. Following that trip, Gross returned to the country dozens of times, both for personal and professional visits.

Some of his most fascinating visits were during the ’90s when Gross began working on development projects in the West Bank. He has more than 25 years’ professional experience in the field of international development, and worked for years as a contractor for the U.S. Agency for International Development.

His work in the territories included a project to improve the health, production capacity and life expectancy of dairy goats owned by Palestinian farmers, and a plan for expanding trade by improving the border crossings between Israel and Gaza.

While working on the dairy project, Gross spent weeks staying in Ramallah hotels, where he says he usually “felt safe and welcome.” His last visit to Gaza, however, was not so pleasant: It took place in 2005, around the time of Israel’s disengagement from the Strip, and ended with Gross being caught in the middle of a firefight between two rival Palestinian factions.

Alan Gross in Tel AvivCredit: Courtesy

“We were driving toward one of the border crossings to return to Israel when, suddenly, we heard gunfire from different directions,” he recalls. “The driver stopped the car and ran out, with the motor still working. I grabbed my computer and got on the floor. After some time I noticed that every few minutes the shooting was replaced by yelling, before it resumed again. So I realized this is the pattern, and when the shooting stopped and the yelling began, I moved. That’s how I eventually made my way out to the crossing.”

Working for the CIA or Mossad?

It was also Gross’ international development expertise that took him to Cuba in 2009, to work on a satellite communications project.

He visited Cuba five times that year, focusing solely on the local communications project. But on the fifth visit, on the night he was supposed to fly back to the United States he was arrested by the Cuban regime, which falsely accused him of working for the U.S. intelligence community.

“It happened on the last night of my trip,” Gross recounts. “Thursday December 3, 2009. My flight was early next morning. As I was drifting into sleep in my hotel room, there were loud knocks on the door – it was the police. They arrested me, and the next time I was a free person was five years later, on December 17, 2014. Everything that happened in-between – well, that’s the subject of my book, which I’m working on. It was not a great experience.”

Gross says the first year of his imprisonment was the hardest. “It felt like cultural starvation,” he reflects. “I had no books, no television, no radio and very little contact with the outside world. I was completely in the dark. Judy visited me for the first time after seven months.”

During his second year in prison, he was allowed to “go outside sometimes and get to see the sun,” within the boundaries of a fenced yard.

I ask Gross if the fact that he was Jewish, with a long history of work and travel in Israel, came up during his lengthy interrogations in prison. “At one point they accused me of being either a CIA or Mossad agent,” he recalls. “I had a good laugh out of that – but of course I wasn’t, just to be clear.” Gross jokes that since moving to Israel, he’s been “kind of disappointed” not to receive a call from Israel’s Defense Ministry.

The only other time his Jewish identity seemed to come up was during the High Holy Days. These were the only times they gave him meat – and it was pork: “I don’t observe kashrut, but to eat pork on Yom Kippur – that’s a bit too much for me.” Still, Gross stresses that he doesn’t think his Jewishness was a factor in his ordeal.

One of Gross’ cellmates – a Catholic Cuban citizen who was detained for trying to smuggle his own family out of Cuba – decided to fast with Gross on Yom Kippur, as an act of friendship and solidarity. The two became close friends.

“We made an oath to each other that, one day, when we were both free and in the U.S., we would go together to a very specific restaurant in Little Havana in Miami. And we did. He got out a year after me, he’s safe in America now, and we went to that restaurant together. It was very good.”

Over time, Gross’ conditions improved – he was allowed to read books, watch television and at some point even use a computer, though it wasn’t connected to the internet.

One thing that didn’t improve, though, was his wellness: Gross lost 115 pounds (52 kilograms) during his time in prison, and his general health deteriorated. He told Haaretz that three things helped him survive: physical exercise; humor; and constantly reminding himself of his family’s history during the Holocaust.

Gross grew up hearing stories about “six brothers and one sister from the family who all miraculously survived.” As he was sitting in his jail cell and counting the days, he says he knew his ordeal “was not tougher than theirs, and we are from the same gene pool – so that gave me hope that I would be strong enough to survive.”

His health continued to deteriorate and at some point in 2014, he announced a hunger strike.

At the same time, the Obama administration was pushing for a major diplomatic breakthrough with Cuba, which would include the release of Gross and members of “the Cuban Five” – a group of Cuban intelligence agents who were arrested in the United States in 1998.

A nervous president

Gross began sensing the end of his captivity was near about a month before his release, when he saw his picture on Cuban television for the first time. He was also hearing slightly optimistic messages from his lawyer, Scott Gilbert, but “there were disappointments before, and it was very hard to deal with.” Instead, he adhered to a simple approach with regards to his release: “I’ll believe it when I see it.”

That moment finally arrived on the first day of Hanukkah in 2014 when Air Force One landed in Cuba, carrying Judy Gross, Gilbert and three senior American lawmakers – Sen. Patrick Leahy, Sen. Jeff Flake and Chris Van Hollen, who represented Gross’ congressional district in Maryland (he is now a senator).

Gross recalls arriving at a military airport outside of Havana and seeing a great spread of food (“It reminded me of breakfast buffets at hotels in Tel Aviv”). The small crew had no time to eat, though. “Sen. Leahy said, ‘I didn’t come here to eat, I came to get Alan out of here. Let’s go!’” On the plane itself, “there were corned-beef sandwiches and latkes,” Gross recounts.

However, Gross had lost a number of teeth during his time in prison, which made it difficult for him to eat. “I was trying to think how to get around this corned-beef sandwich when suddenly one of the flight attendants came to me and said, ‘Mr. Gross, there’s a call for you.’ I asked who was calling me and she said, ‘I believe it’s the president.’ I was holding the sandwich in my hand, I thought about it and said, ‘Well, OK, the sandwich will wait.”

During the 2008 presidential election, Gross had volunteered on Obama’s campaign, focusing on get-out-the-vote efforts in the state of Virginia. When he got on the phone, however, he felt Obama was a bit shy – “he didn’t know if I was angry at him or not.”

Gross says he was not, and that actually while he was in prison he sent Obama a personal letter expressing his support for the president and telling him, “I wouldn’t want to be you.”

“I think I wrote those words because I saw everything he had to deal with at the time,” Gross explains. “Iran, North Korea, Russia, China, Cuba, terrorism, mass shootings, natural disasters, the economy. I told myself, he also lives in a prison. Although it’s true that the conditions in his prison were better than mine.”

On the phone, Obama invited Gross to visit the White House, together with Judy. He told Obama in advance that they would be honored to come, but that he was “not a Rose Garden kind of guy” – meaning he wouldn’t want to turn his visit to the White House into a media circus. Obama, according to Gross, understood immediately. The visit itself, Gross says, was a “great experience.”

Home, but not really home

Gross returned to a different life. During his time in prison, Judy had to sell the couple’s house in Maryland and move to an apartment in Washington because of mounting legal fees and the loss of her husband’s income. One of their daughters made aliyah to Israel, where she met her future wife. (A year after his release, Gross became a grandfather for the first time.) And while he was giving interviews and traveling to different corners of the United States for speaking engagements, Gross felt like he wasn’t fully at home.

“It literally wasn’t the same home,” he says. “I was doing all these speaking engagements, talking about what happened in Cuba. I remember thinking to myself, I don’t want to cry over what I’ve lost; I can’t get those five years back. I wanted to focus on the future.”

In February 2015, the Grosses flew to Israel to visit their daughter in Jerusalem. Over there, he recalls, “I felt at home. It was so good to be back.”

He had not been to Israel in nearly a decade and the visit brought back his old dream of making aliyah. It took a few more visits, but eventually, this past May, Alan and Judy officially moved, settling into their new home in Tel Aviv.

“We had a hard time choosing between Tel Aviv and Jerusalem,” he admits. “Judy thought Jerusalem was more romantic, and we have a daughter and granddaughter over there. I preferred Tel Aviv. I like Jerusalem, but I think I’m more made for Tel Aviv.”

Some his favorite spots in the city include Carmel Market, the beach promenade and Falafel Hakosem on Shlomo Hamelech Street.

Becoming a new immigrant in Israel “was a very easy process,” according to Gross. “We got our passports, ID cards, bus card, health insurance card, and everything was very easy to obtain. At some point I asked myself, ‘Why didn’t I do this earlier?’”

Gross is still accepting invitations for speaking engagements in the United States, but feels “there is more in life than doing these speaking engagements, and I want to start something new.”

One thing he’s keen to revisit is economic cooperation between Israelis and Palestinians, including his old idea of improving the trade mechanisms at the border crossings between Israel and Gaza.

Gross wasn’t impressed by President Donald Trump’s recent speech recognizing Jerusalem as the Israeli capital, which he says was “nothing more than a wasted opportunity to accomplish something meaningful.”

Peace, says Gross, will require practical and meaningful steps on the ground, not speeches, and he hopes to once again be able to personally contribute to that effort.

“I still want to make things better. That’s always been the one goal I had in front of my eyes,” he says. “I’ve had a lot of time to think about this, and I know that right now I’m just not ready yet to hang up my boxing gloves.”

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