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Zuckman Crosses Cultures in Quest to Free Cuban Prisoner Zuckman Crosses Cultures in Quest to Free Cuban Prisoner

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Zuckman Crosses Cultures in Quest to Free Cuban Prisoner

Jill Zuckman(Photo courtesy of Jill Zuckman)

photo of Christopher Snow Hopkins
May 4, 2014

When Jill Zuckman arrived at the Carlos J. Finlay Military Hospital in Havana last Tuesday, she was taken into a small room with four chairs and a low table with coffee, water, and candy.

Sitting opposite her was Alan Gross, a former subcontractor for the U.S. Agency for International Development who was arrested by the Cuban government four years ago on charges that he had committed “acts against the independence or territorial integrity of the state” after trying to bring Internet access to Cuba’s Jewish population. The prisoner muttered something that Zuckman asked him to repeat.

“On May 2, I turn 65 years old and it will be my last birthday here,” Gross said. “It means what it means.”


Zuckman, a managing director at SKDKnickerbocker, is a communications specialist working to have Gross freed. She says the case is one of the most challenging assignments of her career, which she began as a political reporter and continued as communications director at the Transportation Department.

At the time of the meeting, Gross was recovering from a nine-day hunger strike. He had once been a burly man but has lost 110 pounds over the course of his imprisonment. Zuckman and her two companions—Scott Gilbert, Gross’s lead attorney, and Emily Grim, an associate at Gilbert’s law firm—were astonished that he was still alive.

“He turns 65 on Friday, and I really think that puts [pressure on] the two governments,” said Zuckman, who is working on the case pro bono. “I think [the U.S. and Cuban] governments have to decide whether they’re going to make some hard decisions and get him out of there, or whether they’re going to have his blood on their hands.”

The case has received intermittent press attention since Gross was arrested in 2009, yet the primary target of Zuckman’s advocacy campaign is senior government officials.

“It’s very difficult because we’re not necessarily trying to communicate to regular, everyday people,” she said. “We’re really trying to communicate to the highest levels of both governments.”

Here at home, Zuckman’s PR campaign—and a website documenting the deterioration of Gross’s health—seems to be getting results. In December, the White House said that President Obama was “personally engaged” in the campaign to free Gross and had urged world leaders to use their influence with the Cuban government to set him free.

Zuckman, 48, was born in Washington. Her father was a law professor at Catholic University, and her mother was a social worker.

After graduating from Brown University, Zuckman became a reporter for the Milwaukee Journal, then returned to D.C. to report for Congressional Quarterly, The Boston Globe, and finally the Chicago Tribune. Over the course of her career, she covered four presidential campaigns.

At the beginning of 2009, Zuckman left the Tribune to serve as director of public affairs in the Transportation Department under then-Secretary Ray LaHood. In the ensuing years, she helped LaHood draw attention to the dangers of “distracted driving” and also coordinated the agency’s media response during the 2013 government shutdown, when the Federal Aviation Administration furloughed thousands of air-safety inspectors.

Oddly enough, Zuckman became involved in the effort to free Alan Gross after meeting Gilbert at a bar mitzvah. A few months later, Gilbert called Zuckman to ask if she would be interested in helping with the case.

“It was completely random,” she said.

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