Bridges to Cuba

Will the quiet power of cultural diplomacy change a nation?

by Paul Hond Published Fall 2016
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Illustrations by Edel Rodriguez

As a light rain fell on José Martí International Airport in Havana, the Boeing VC-25 aircraft appeared against a battleship-gray sky. The plane got closer, and the words on the fuselage became visible: UNITED STATES OF AMERICA.

Air Force One touched down on the runway, taxied, and stopped. The door opened, and the president of the United States, Barack Obama ’83CC, emerged at the top of the stairs. He snapped open a black umbrella and disembarked with his wife, Michelle; their two daughters, Sasha and Malia; and Michelle’s mother, Marian.

It was March 20, 2016. Not since 1928, when the USS Texas carried Calvin Coolidge a hundred miles from Key West to Havana, had a sitting US president come to Cuba.

Obama stepped onto the tarmac, and a line of Cuban and American officials welcomed him. “Hi, Jeff. Good to see you. How are you?” Obama said, shaking hands with Jeffrey DeLaurentis ’78SIPA, the chargé d’affaires at the US embassy in Havana and the top US diplomat in Cuba.

An hour later, DeLaurentis stood on a podium beside the president in the Meliá Habana hotel. DeLaurentis had first been sent to Cuba twenty-five years earlier, during the worst economic disaster to ever hit the Communist-led country. Now, in a scene he could not have imagined then, he was in Havana introducing three hundred US embassy employees and their families to the president of the United States.

“Mr. President,” he said, “this is your embassy team, Americans and Cubans, and they want to say thank you for giving them the opportunity to live history.”


Angela Mestre, a Columbia College junior, was living two histories that rainy day in Havana. As President Obama’s motorcade crept along the highway beside the Malecón, the seawall esplanade that skirts the Straits of Florida, Mestre watched it go by. The whole city was watching: people lined the streets or leaned out over their flaking balconies to glimpse a leader who, Mestre says, “of all US presidents is the most relatable to Latin American and Caribbean people. There’s real affection for Obama. People love him.”

Mestre was one of four Columbia students who were spending the spring semester in Cuba through the Consortium for Advanced Studies Abroad (CASA), an eight-university collaboration that gives college juniors access to the University of Havana and Casa de Las Américas, Cuba’s leading center for Latin American studies. As another Columbia student, Caleb Murray-Bozeman, puts it, “The classes are great” — he studied Cuban cinema and Latin American thought and took Tendencies of Contemporary Capitalism (“not as propagandistic as I’d expected”) — “but the focus of the program really isn’t on the coursework. It’s to get us out into Havana to experience Cuban culture.”

For Mestre, the decision to go to Cuba was fraught. Both her parents are Cuban-American. Her mother was born in Bogotá, Colombia, to Cuban parents, and her father was born in Cuba but left in the early 1970s. Mestre was the first in her family to return to the island, and the older generations were torn. “The emotional component, the identity issues, are very complicated,” says Mestre. “It’s difficult to consider that somebody you love would go back to a country that you feel ousted you.”

Mestre was raised on stories of the lost paradise of the 1950s: the one-movie-theater town where her father grew up; the houses and mansions; the vibrant Havana life. “To see the remnants, the ghosts of these stories, is really cool, but of course there have been monumental changes in the past sixty years,” Mestre says.

Obama’s visit was one of them. In the days before his arrival, some buildings, their pink and blue arcades long sunk into a peeling grandeur, had been slapped with fresh coats of paint, and stores (most are state-run) were closed (Murray-Bozeman heard that this was because the Cuban government, sensitive to Soviet-era imagery, didn’t want the Americans to see any lines). There was a buzz, a flutter, a high anticipation mixed with uncertainty.

“People are excited that things are opening up,” says Mestre, “but also apprehensive. The challenge for society is that once the country opens up, it becomes exposed and vulnerable to being overrun. There’s rarely been a country where every remedy is such a double-edged sword.”


Three weeks after Obama’s visit, Jeffrey DeLaurentis, wearing a light-blue seersucker suit, sits in a cushioned chair in his office at the US embassy in Havana, a concrete and glass box built in 1953 in the International Style. The building sits in modest atmospheric isolation on the edge of the Vedado neighborhood, overlooking the Malecón and the sea.

DeLaurentis had joined the Foreign Service with visions of Prague and Budapest dancing in his head. But the world had other plans. In 1991, Cuba, crippled by the collapse of the Soviet Union, suffered food shortages and blackouts, and DeLaurentis was dispatched to the US Interests Section in Havana, a consular niche set up in the 1970s in lieu of formal relations and based in the erstwhile US embassy building. There, he served as vice consul, processing visas and managing the refugee program. He left in 1993 and returned in 1999 for three years as the political-economic section chief. He never did get to the Danube. His latest Cuba tour began in August 2014.

Now, as head of the US embassy in Havana (the title “chargé d’affaires” is an interim designation until an ambassador is nominated and confirmed), DeLaurentis recounts one of the more sensitive diplomatic forays of the post-Cold War era.

“When President Obama came into office, in 2009, the administration made some initial changes to facilitate more travel to Cuba, more remittances, more people-to-people contact,” he says. “But efforts to develop a different approach with Cuba really came to a halt in December 2009 after the unfair — and unjustifiable — incarceration of Alan Gross, the development worker.” Gross, a contractor with USAID, was imprisoned for smuggling illegal Internet equipment to Cuban civilians.

In 2013, the US and Cuba began secret negotiations in Canada, with the backing of Pope Francis, resulting in an exchange of intelligence officers. “The Cubans also agreed to release Alan Gross as a humanitarian gesture, free fifty-three political prisoners, look at increased Internet access, and engage with the Red Cross and other international organizations,” DeLaurentis says. “And President Obama announced our decision to do a full and scrupulous review of Cuba’s place on the State Department’s terrorist list.” (That review, which was completed in April 2015, found that Cuba should be taken off.)

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