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Cuban President Fidel Castro, shown in Paris in 1995. Four years earlier, he first met Vicki Huddleston, the U.S. State Department's lead diplomat in Cuba. In a new book, Ms. Huddleston recounts her experiences as an American envoy to the Communist nation.

Charles Platiau/Reuters

Ambassador Vicki Huddleston served under presidents Bill Clinton and George W. Bush as chief of the U.S. Interests Section in Havana. Her report for the Brookings Institution about normalizing relations with Cuba was adapted for President Barack Obama’s diplomatic opening with Raul Castro in 2014. Her new book is Our Woman in Havana: A U.S. Diplomat’s Chronicle of America’s Long Struggle with Castro’s Cuba, from which this essay is adapted.

I first met Fidel Castro in 1991, shortly after I became the U.S. State Department’s lead diplomat on Cuba. I had travelled from Washington to Havana for a celebration marking Mr. Castro’s withdrawal of 50,000 Cuban troops from southern Africa. At 64, his famous beard was greying, but he was still a handsome man, over six feet tall, with a booming voice and charismatic presence.

In a room filled with officials from around the globe, Mr. Castro directed his attention toward me, asking, “Who are you, someone’s spouse?” He knew exactly who I was, I had visited Cuba several times as deputy and he absolutely knew I was not in attendance merely because I was “someone’s spouse.”

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As I drew myself up for an appropriate response, I became aware that the entire room was listening for my reply. I stood as tall as possible, all five feet, five inches of me, and announced boldly, “No, I am the director of Cuban affairs.” Fidel, purring with pleasure, surveyed the room to ensure no one would miss his retort: “Oh? I thought I was!” My delegation was speechless. I was angry and embarrassed.

Ten minutes later, speaking rapidly and passionately, Mr. Castro complained that the American bolqueo or blockade was killing Cuba’s children. “That’s not true,” I almost shouted. “When Cuba holds free and fair elections with international observers we will lift the embargo.” Fidel fumed, “You will never give up the bloqueo, the gusanos” – or worms, his term for the Cuban Diaspora – “won’t allow it.” As he stomped off he snagged a very large straight-up martini.

A poster of Fidel and Raul Castro in Havana on April 18, 2018.

Ramon Espinosa/The Associated Press

Despite our tense encounter, I was delighted to return to Havana in 1999 as chief of the U.S. Interests Section and hopeful that I could advance a fledgling opening by President Bill Clinton to the country. Standing on the fifth-floor balcony of the obsidian-coloured building that was the U.S. Interests Section – now our ill-fated and mostly abandoned embassy – I wondered how a girl from Hungry Horse, Mont., could have been so fortunate. From the balcony, I had a panoramic view of the Malecon, the city’s esplanade and seawall built in the early 1900s by the U.S. Army Corps of Engineers, and the elegant Hotel Nacional where mob boss Lucky Luciano once hosted a conference for the heads of major U.S. crime families. Further along the green water of the Caribbean, I could just make out the columns of the USS Maine monument dedicated to the American sailors who died when their ship blew up in Havana Bay, triggering the Spanish-American War in 1898. I loved the city, no matter how ravaged by time and neglect.

However, my dreams of being a handmaiden to improved U.S.-Cuba relations were sunk when a little Cuban boy named Elian Gonzalez was found floating on an inner tube in the Florida Straits after his drowning mother had tied him to it. Cuban-Americans demanded that he remain with them in Miami, but Mr. Castro wanted him back. In June, 2000, after a six-month media battle, Mr. Clinton sent Elian home to his father and to a victorious Mr. Castro, who had for a final time walked the world stage before falling ill and handing over power to his brother, Raul.

Miami, April, 2000: Elian Gonzalez is held in a closet by Donato Dalrymple, one of the two men who rescued the Cuban boy from the ocean, as government officials search the home of Lazaro Gonzalez for the child.

Alan Diaz/The Associated Press

Fidel Castro reputedly said in 1976 that relations wouldn’t be normal until there was a black American president and a Latin Pope. Finally, almost 40 years later, the Stars and Stripes were hoisted in front of our newly christened embassy, the building where I’d once watched Fidel, his seldom-seen wife, Delia, and a jubilant crowd celebrate Elian’s return. A year later, Raul, not Fidel, hosted the United States’ first black president. But this opening is now faltering, as President Donald Trump, at the behest of his conservative Cuban-American backers, has returned to a punitive policy.

And now, Cuba’s President is no longer a Castro. In a country where Fidel and Raul ruled for the past 59 years, the succession is a seismic shift, which may bring little change in the near-term but tomorrow may bring down mountains.

Two historic hand-holdings by Cuba's Raul Castro: With then U.S. president Barack Obama in 2016, and with new Cuban President Miguel Diaz-Canel in 2018.

Ramon Espinosa and Alexandre Meneghini/The Associated Press

On April 19, 2018, Cuba’s National Assembly elected Miguel Diaz-Canel, formally initiating the transfer of power from those who led the revolution to a generation born after their triumphant entry into Havana on Jan. 1, 1959. The smooth succession to a civilian, and a non-Castro, underlines the strength and longevity of Cuba’s one-party authoritarian government. It also begins a process that, if successful, will over time give Cubans freer and richer lives as technology and communications increasingly connect them to the Caribbean and the Hemisphere.

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Chosen and mentored by Raul, the 58-year-old Mr. Diaz-Canel could be a Raul clone. Unassuming, pragmatic and not a natural heir to the charismatic Fidel, he lacks either of the Castro brothers’ revolutionary credentials. He will find it challenging to reconcile the demands of the Castros’ contemporaries – who are resistant to economic and political reform – with the aspirations of a younger generation of Cubans who want better jobs and fuller lives.

Mr. Diaz-Canel is not a leader to take on lost causes. During his time as secretarygeneral of the Communist Party in the province of Holguin, a joint venture by the Cuban government and Canadian mining firm, Sherritt International, caused environmental degradation to nearby rivers and coastal areas, according to the Association for the Study of the Cuban Economy. A loyal party stalwart, Mr. Diaz-Canel probably assumed there was little he could do because the Cuban government, which owned 50 per cent of the enterprise, had granted the venture an exemption from its environmental code, also according to the ASCE.

In 2002, I saw first-hand the ravages of this mining operation when a colleague and I took a road trip down the middle of the island on the Carretera Central. After Santiago de Cuba, we crossed the Sierra Maestra on a winding highway built through the mountains by Mr. Castro’s revolutionary government to Baracoa, the island’s original capital. We stopped at the Alejandro de Humboldt National Park to admire efforts to preserve Cuba’s most lush biodiversity, and less than an hour later, we approached the town of Moa where Sherritt was headquartered. On the side of the highway, large grey pipes carrying polluted water from the nearby mines spurted brownish liquid. Every few miles, signs sitting in stale, red puddles and ponds warned us not to trespass and not to take photographs. Heavy, dark clouds billowed over rows of dun-coloured dormitories for workers, as we drove through town and then past open checkpoint gates and into the enormous open-pit mine. It was otherworldly, akin to Dante’s Inferno, as each level became yet a wider expanse of barren, red earth.

It is no surprise that Mr. Diaz-Canel would not confront Sherritt or his own government, as he is a product of the party bureaucracy that follows orders from the top. Nevertheless, once he has proven himself and gained the trust of the party’s old-guard that is hardwired to unquestionably follow Fidel Castro and his revolutionaries, he will have to take initiative and jump-start the stalled reforms, otherwise Cuba will sink deeper into debt and become increasingly dependent on its Russian and Chinese benefactors.

Jan. 20, 2017: A man watches President Donald Trump's inauguration speech on television in Havana.

Ramon Espinosa/The Associated Press

Tense times in Havana

“No es facil!” “It’s not easy!” A refrain that I often heard in Cuba is still true today. Millions of Cubans, whose expectations of a better future were raised by president Barack Obama’s opening, now are disillusioned. Mr. Trump in an angry speech to Cuban exiles in Miami cancelled the opening and tightened sanctions on travel and investment. The so-called “sonic attacks” caused even more damage to U.S.-Cuba relations. Responding to entreaties by Cuban-American senator Marco Rubio, Mr. Trump ordered American diplomats and their families home from Cuba. Although there were no injuries to anyone other than the diplomats, the State Department issued a travel warning that resulted in a significant reduction of visitors, damaging the fledgling private sector, which supplied travellers with board, room and souvenirs.

In contrast, the Canadian government dealt with the injuries to its diplomats in a low-key and thoughtful manner. Recently, it sent home the families of its diplomats – but not the diplomats themselves. In stark contrast to the United States, the Canadian government did not warn its citizens not to travel to Cuba. Raul Castro’s daughter Mariela labelled the injuries the stuff of Star Wars, and Foreign Minister Bruno Rodriguez denied that Cuba was responsible. The Guardian newspaper reported that some scientists blamed mass hysteria; they contend that sonic devices could not cause such a wide range of injuries, from mild brain trauma to loss of hearing. But Douglas Smith at the University of Pennsylvania’s Perelman School of Medicine, who assessed 24 U.S. diplomats, said that they looked “exactly like the patients we would see in a concussion clinic.”

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An American flag flies at the U.S. embassy in Havana.

The Associated Press

Discovering the culprit – whether a faction of the Cuban government, a foreign country such as Russia or China or malfunctioning listening devices, as suggested by University of Michigan scientists – won’t repair the bilateral relationship. Mr. Trump, in a bizarre tweet shortly after Mr. Diaz-Canel took office, said, “We love Cuba. We’re going to take care of Cuba. We are going to take care of it.” It is hard to say what Mr. Trump’s words signify, but given his most recent appointments, U.S. policy is likely to become harsher and more threatening. Mr. Trump’s newly appointed national-security adviser, John Bolton, attempted to undermine former president Jimmy Carter’s visit to Cuba in 2002 by falsely claiming that Cuba had a “developmental biological weapons program.” In 2016, Mike Pompeo – confirmed on Thursday as Mr. Trump’s new Secretary of State – wrote an opinion piece claiming that Mr. Obama’s historic visit to Havana encouraged dictators.

Rather than threatening, the Trump administration should seize the opportunity to engage Mr. Diaz-Canel’s new government. The Obama administration’s opening to Cuba, from 2014 to 2017, allowed Raul Castro to quicken economic reform, leading to more than 600,000 Cubans working in the private sector and many managing their own small businesses. Young people began connecting more than ever to the internet and travelling to Florida to buy computers and communications devices. In return, their relatives visited Cuba, bringing new ideas and cash to help them set up businesses that catered to the influx of tourists. But with the shuttering of the U.S. embassy’s consular section, Cubans are now unable to obtain visas to travel to the United States, and the travel warning has resulted in a sharp decline in American visitors. In response to a hostile Trump administration, Raul Castro slowed reforms, tightened controls over the private sector and again put off unification of Cuba’s dual currency – a move sorely needed to attract foreign investment.

By reinstating a punitive policy toward Cuba, the Trump administration is ignoring the strategic interests of the United States. Accustomed to always having a patron – Spain, the United States, the Soviet Union and Venezuela, the last of which can no longer afford to sustain the relationship – Cuba is moving ever closer to Russia and China, giving them a beachhead just 150 kilometres from Florida. Mr. Trump also flouts the desires of Canada and our friends and allies around the world, who have taken the unusual step of voting for the end of the U.S. embargo at the United Nations. Cuba is the only country in the world against whom the United States maintains a comprehensive, unilateral embargo – not even Syria, which has gassed its own people, or North Korea, which has threatened missile strikes with nuclear warheads.

My personal experiences in Cuba led me to the realization that repeating a failed policy time and time again will not lead to a different outcome. Rather, it will only postpone reconciliation among the Cuban people – both those abroad and in the country. One incident more than any stands out in my mind. In the spring of 2002, I was driving the U.S. mission’s official black armoured sedan down tree-lined Quinta Avenida (Fifth Avenue), sometimes called Avenida de las Americas. Seeing a group of teenagers looking for a ride, I stopped the car. Five or six youngsters happily squeezed into the back seat. Suddenly, realizing that this vehicle was something special, one of them asked what type of car it was. At that time, there were generally three types of cars in Cuba: clunky 1950s American cars, little white Ladas and black Mercedes-Benz taxis. This meant that no one except foreign diplomats drove new American vehicles. I replied, “It’s a Ford Crown Victoria,” which promoted one young lady to ask, “Who are you?” I replied, “I am the chief American diplomat.” There was a silence, and I wondered if my passengers would ask that I immediately stop and let them out. Then the young woman said, “Be our mother, take us to Miami!”

Those words left me with the realization that Cuba’s youth deserve a future in Havana, not Miami.

Motorists drive along the Malecon in Havana.

Kevin Van Paassen/The Globe and Mail

Editor’s note: An earlier version of this article, referring to the new leader’s views incorrectly suggested a Canadian mining company caused environmental degradation in Cuba. In fact, the reference was to a joint venture between the Cuban government and the Canadian company Sherritt International with the information based on a report by the Association for the Study of the Cuban Economy.
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