Zuckman Crosses Cultures in Quest to Free Cuban Prisoner

Jill Zuckman
National Journal
Christopher Snow Hopkins
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Christopher Snow Hopkins
May 4, 2014, 7 a.m.

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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