It was September 1999, at the U.S. Interests Section, Havana, Cuba. Standing on the fifth-floor balcony of the steel and glass building that shines like iridescent obsidian, I wondered how a girl from Hungry Horse, Montana, could have been so fortunate.

President Bill Clinton had sent me to Havana to lead our diplomatic mission, the U.S. Interests Section, which had once been the called the U.S. embassy. From the balcony I had a panoramic view of the Malecón, the city’s esplanade and seawall; the elegant Hotel Nacional, built on a bluff overlooking the green waters of the Caribbean; and, farther on, the white columns of the USS Maine monument, dedicated to sailors who died when their ship blew up in Havana Bay in 1898. In the distance I could see the great old fort, the Castillo de los Tres Reyes del Morro, that once guarded Havana Bay and the gathering of Spanish galleons bursting with Inca and Aztec plunder.

After working on U.S.-Cuba relations from 1989 to 1993, I had become ensnared by the two countries’ dysfunctional relationship and developed a deep and abiding interest in the issue. But I couldn’t continue in the same job. At the State Department four years was a long time to work on the same country, so for the good of my career it was time to move on. I served in Haiti, then Madagascar, and then returned to Washington, D.C., as a senior policy maker for Africa. But I kept dreaming and watching for an opportunity that would bring me back to Cuba, an island nation lost in time but so close to our southern shore and our national psyche.

During the next three years of my assignment, I would have an opportunity to see what I could do to heal the wounds left by Fidel Castro’s failing revolution and our destructive policy, which together managed to deprive the island and its people of their future. I loved the magic of Havana, the spirit of its people. I hoped that I might begin to untangle the contradiction, lies, and myths that from the beginning had been too present in our unhappy relations.

The contradiction that haunts our relationship with Cuba is that the United States has always coveted the island. And perhaps this foundational contradiction is what makes the U.S.-Cuba relationship so fractious. In 1805, President Thomas Jefferson considered annexation, while Secretary of State John Adams believed that, like “a ripe fruit,” Cuba would fall to the United States when severed from Spain. The Monroe Doctrine was very much directed at keeping European nations out of Latin America, and especially the Caribbean region, which we have long considered our backyard. If even a friendly foreign power gained influence in the region, it would be at our political and economic expense. Cuba, the biggest island in the Caribbean, only 90 miles from Key West and thus our closest neighbor after Canada and Mexico, was the greatest prize. In all likelihood, Cuba would have become a U.S. state or territory had Henry Teller, a senator from Colorado, not persuaded his colleagues to vote for an amendment to the War Powers Act that prohibited annexation while authorizing the conflict with Spain on the eve of the 20th century.

One of the first lies or myths (whichever you prefer) was the sinking of an American warship, the USS Maine, in Havana Bay. The United States, inflamed by the yellow press and a new sense of nationalism, blamed Spain. The rallying cry “Remember the Maine, to Hell with Spain,” convinced Americans that Spain blew up the ship, but it was a malfunction in its boilers that actually sank it. Spain lost its “Ever-Faithful Isle,” as well as Guam, the Philippines, and Puerto Rico in the Spanish-American War of 1898, which began in Cuba. Lieutenant Colonel Teddy Roosevelt and Colonel Leonard Wood, who led the Rough Riders’ victorious charge up San Juan Hill, strongly advocated for the war that belatedly made the United States a colonial power. In turn, Cuba gave Roosevelt fame and the opportunity to claim the vice presidential spot in the 1900 election. A year later William McKinley was assassinated, and Roosevelt became president of the United States. Both Roosevelt and Wood continued to play outsize roles in Cuba’s history. Together they initiated a process that pushed the United States into becoming the predominant political and economic power in Cuba. Roosevelt insisted that Cuba cede the lower half of Guantanamo Bay and allow the United States to control its foreign policy. His superior officer during the battle outside Santiago de Cuba, Leonard Wood, became a general officer and our first military governor of Cuba.

The influence of the United States in Cuba was overwhelming, first through our occupation and then through vast amounts of American investment. Over time Havana and, to a lesser degree, the whole island became a playground for Americans. Havana’s casinos and nightclubs were run by the American Mafia and Fulgencio Batista, Cuba’s corrupt dictator. Income inequality, corruption, and state-sponsored violence resulted in young, idealist Cubans confronting Batista in Havana. Castro was better organized and better funded than the urban opposition, which supported him as his military campaign in Cuba’s eastern provinces gained momentum. But few suspected that Castro would ally Cuba with the Soviet Union and transform the island into a communist nation, the first in the Western Hemisphere.

Cuba, while geographically close, became shrouded in mystery. The first crack in the island nation’s isolation didn’t occur until 15 years after the Cuban Missile Crisis. In 1977, President Jimmy Carter and Fidel Castro reestablished relations under another name. A bilateral agreement set up the U.S. and Cuban Interests Sections, rather than embassies, in one another’s capitals, which were overseen by “principal officers” rather than ambassadors. By the terms of the agreement, American and Cuban diplomats worked in their former embassies, but were prohibited from flying the flag of their respective countries on the other’s soil. There was a good reason for this sleight of hand: Cuban Americans vehemently objected to diplomatic relations with Cuba. Had an American flag been raised outside the former embassy building, it would have appeared as if the United States had reestablished its embassy and normal diplomatic relations.

Most Americans and even the media believed that we didn’t have formal relations until December 17, 2014, when President Barack Obama announced that the United States had reestablished diplomatic relations with Cuba. Without the Stars and Stripes flying, Americans—even those who watched on television as Fidel Castro led massive marches past the Interests Section in 2000, demanding the return to his nation of a Cuban child—didn’t think we had relations. This impression was further enhanced by the fact that the Swiss government was our official diplomatic representative in Cuba. Most Americans—even those who visited Havana—had the impression that if American diplomats were in Cuba, they were working from a back office within the small Swiss embassy located on the Avenida de las Americas. In fact, the tiny Swiss embassy did little more than provide us with stationery that proclaimed, “Embassy of Switzerland” at the top and, below, “The US Interests Section.” This added an extra layer of illusion to the myth that the United States didn’t have a presence on the island when, in fact, ours was the largest diplomatic mission in Cuba.

The Interests Section in Havana is unique. It is a hybrid of the American Institute in Taiwan and our consular missions in Hong Kong and Jerusalem. The American Institute is a de facto embassy representing U.S. interests in Taiwan through a private corporation run by U.S. diplomats. But unlike the Interests Section, it does not have diplomatic status. Our Interests Section in Havana is also similar to our consulates in Hong Kong and Jerusalem, which represent the United States at a lower level than an embassy would. But Cuba is neither a large urban area like Hong Kong nor a disputed city like Jerusalem. Rather, it is a country that is recognized by every other nation in the world. The contradiction was maintained simply to appease the Cuban American community, which had the political clout to force the U.S. government to pretend that the United States and Cuba didn’t have diplomatic relations.

When I arrived in Havana in September 1999 to lead the Interests Section, Clinton was making his second attempt to improve relations with the island. But his efforts were only the latest in a series of secret and not-so-secret talks with Castro on the part of Democrats and Republicans alike. These behind-the-scenes negotiations were sometimes wrecked by divergent views, and other times by fear of political retribution by the Cuban American National Foundation (CANF) or by Castro himself. Secretary of State Henry Kissinger had hoped to open up to Cuba as he had China, but the initiative stalled. President Richard Nixon never trusted Castro, and his successor Gerald Ford was considerably less interested in Kissinger’s project.

Clinton’s second attempt to open up relations began with an exchange of information on possible terrorist attacks in the United States and in Cuba. (His first attempt had crashed with the downing of two civilian aircraft by Castro in 1996.) The Colombian author Gabriel García Márquez was sent by Castro to serve as a liaison, and his mission resulted in a visit by the FBI to their counterparts in Havana. Cuban officials hoped that the information they provided would be used to stop exiles from carrying out attacks on the island. To their dismay, soon after the exchange the FBI arrested five Cuban agents who had been working in the United States to expose and infiltrate exile organizations such as the militant groups Alpha 66 and Comandos L as well as Brothers to the Rescue and CANF. The Cuban Five, as they came to be known—either spies or heroes, depending on your point of view—were convicted in a Florida court and received long jail sentences for espionage. This brought about an impasse between the U.S. and Cuba that continued over the next 15 years, ending only with the Barack Obama–Raúl Castro opening when the Cuban spies were exchanged for an American spy and a USAID contractor, Alan Gross, who had been jailed for providing communications equipment to members of Cuba’s Jewish community.

The Interests Section’s size and location on Havana’s seafront made it stand out from other embassies and reflected the fact that it had been the American embassy until President Dwight D. Eisenhower broke diplomatic relations in 1961. One of New York’s premier architectural firms, Harrison and Abramovitz, had designed it shortly before the Cuban Revolution. The building looks like a smaller version of the United Nations headquarters in New York City, also designed by Harrison and Abramovitz. Only Russia’s embassy—an ugly, gray brutalist concrete tower in the Miramar suburb of Havana that was constructed in the ’70s—rivaled our building for prominence, though not for beauty.

“ From the roof of the dugout, we had a good view of Chávez, whose paunchy frame didn’t prevent him from getting the ball over the plate with enough zip to strike out Castro’s old-timers. ”

I was the first woman to lead the Interests Section. Fidel referred to me as the jefa (chief). My official title was principal officer, but Americans and Cubans alike called me Ambassador Huddleston because I had previously held that title in Madagascar. The Cubans liked the idea, and began calling Fernando Remírez de Estenoz Barciela, the chief of the Cuban Interests Section in Washington, D.C., Ambassador Remírez. It gave the illusion of relations at a higher level. My staff consisted of about 50 Americans representing several U.S. agencies and about 200 Cubans. But officially—yet another contradiction—we had no Cuban employees. Like all other foreign entities in Cuba, we did not directly employ our Cuban staff; a Cuban government corporation provided us with local personnel. But we treated them the same as our local staff in embassies around the world; we paid them fair salaries based on their responsibilities and helped fund pensions to which they were entitled when they retired. This confused status of our local employees meant they had two masters: the Cuban state employment agency and the U.S. Interests Section. Moreover, in a few cases our local staff had three masters; some were spies, employed by the Cuban Ministry of the Interior, which is responsible for the internal security of the Cuban state. To protect our secrets, Cuban employees could only access the first two floors of the Interests Section. All of our local employees were forced to report on our activities to the Cuban government if they wished to keep their jobs. If a Cuban employee failed to report on our activities, he or she would be fired and we would find out when that employee didn’t show up for work. On several occasions I protested to the Ministry of Foreign Affairs, but the employees were never reinstated. The best I could do was to extract a promise that the person in question might be sent to work in another diplomatic mission.

Our American staff was much like that at any embassy: foreign service officers worked in the political, economic, administrative, and public diplomacy sections. An Immigration and Naturalization Service annex a few blocks away operated out of a smaller building on the Malecón, the seafront. Its sole purpose was to provide refugee visas to qualified Cuban applicants. Our consular staff of Americans and Cubans issued thousands of visas to Cuban visitors and migrants to the States. By the terms of the 1994 migration agreement, we issued 20,000 immigrant visas annually. Still, this did not stop the exodus of undocumented Cubans.

The consular section, which took up most of the ground floor, also provided citizen services to Americans visiting Cuba, both legally and illegally. Initially those who were illegal were reported to the U.S. Treasury’s Office of Foreign Assets Control (OFAC), which enforced the embargo. I changed this policy because it prevented Americans in need of medical, financial, or other help from coming into the consular section. The new guidelines were simple: consular officers wouldn’t ask the status of American visitors, and by not knowing would not be obliged to report to OFAC. It worked well during my time in Cuba, but I assume my “don’t ask, don’t tell” rule was reversed as relations deteriorated after I left Cuba in September 2002.

Additionally the Interests Section cooperated with the Cuban government on environmental research to ensure the health of Cuba’s coral reefs, which are the principal fish hatcheries for the North Atlantic. We also exchanged information to thwart narcotics trafficking. The Cuban Border Guard informed the U.S. Coast Guard when traffickers used Cuban airspace or waterways. The Coast Guard officer on my staff had excellent relations with his counterparts at the Cuban Border Guard. Occasionally, Cuba returned to U.S. authorities criminals wanted by the FBI.

I expected the Cuban government would be pleased that I was the new American representative. This was the first time that a woman and a former ambassador had been sent to Havana as our chief diplomat. I knew that Castro preferred to deal with women, and a bonus was that I had a title that conferred a higher status on the job. Therefore, I anticipated that I would be able to build a relationship that could lead to improved relations. It turned out that this was not the way the Cuban hierarchy viewed me. In fact, they were wary because a former head of the Cuban Interests Section who didn’t like me—or in my opinion, any woman in an official position—told the Cubans that I was a hard-liner. Still, I wasn’t overly concerned. I planned to build a relationship of trust with Ricardo Alarcón, Castro’s principal adviser on the United States, whom I knew from my years managing Cuban affairs at the State Department.

One of my principal jobs was to meet with Cuba’s human rights activists, an activity that the Cuban government particularly disliked. Concerned about our relations with the dissidents, Castro and the hierarchy monitored these meetings closely. I often wondered why he was so obsessed with the dissident community, given that they had little power or influence within the country. Perhaps he just didn’t like the fact that there were Cubans who were willing to contradict his vision of how the country should be ruled.

I came to know the dissidents very well. There were many small groups that regularly attempted to form a united coalition, but the most conservative dissidents invariably refused to join. The best-known con- servatives were the Group of Four (the regime called them the Gang of Four), which comprised Felix Bonne, Rene Gomez Manzano, Vladimiro Roca Antúnez (son of Blas Roca Calderio, a founder of the Cuban Communist Party); and Marta Beatriz Roque. In the ’70s and ’80s, they had held important positions in universities and the military, but their views led to confrontations with the political commissars and dismissal from their positions. They were jailed for publishing a pamphlet, La Patria es de Todos (The Homeland is for All), which urged Cubans to boycott elections and asked foreign investors to avoid Cuba.

Roque, who was the leader of this group, was as tough as Fidel. Her reputation as one of the country’s leading activists was well earned; she never stopped confronting the government, despite persistent illness that occasionally forced her into the hospital. When I worried about her outspoken comments, she brushed off my concern: “They will jail me no matter what I do or say.” Bonne was my favorite dissident. One of the few major dissidents of African descent, he had been a brilliant electrical engineer until the regime forced him out of his university job. The most militant of the Group of Four were Roca, a Social Democrat, and Gomez Manzano, a lawyer who represented dissidents and then joined them in opposition to the government. In their view, there could be no compromise with the Castro regime. Roca, who had been an elite MiG pilot in the Cuban armed forces before becoming a dissident, was deeply mistrusted by the Cuban hierarchy. In their eyes, he was not only a dissident but a traitor because he had initially fought for the revolution but then dared to defy it.

The best known of the liberal group of dissidents were Oswaldo Payá and Elizardo Sánchez. Sánchez was well known for his human rights monitoring group and Payá would become famous for his Project Varela—named for a Spanish priest and advocating for Cuban independence—which was designed to modify the Cuban Constitution rather than completely reject it. Project Varela was successful in garnering worldwide attention, but it did not—nor did any other dissident activity—pose even the slightest threat to Castro’s rule.

The Group of Four and the liberals from Project Varela faced overwhelming odds. None of them had the charisma of Fidel Castro. They did have forceful personalities, but they lacked followers. The overall lack of communication and transportation made it difficult to spread their beliefs around the country and rivalries further eroded their potential influence. Cuba’s network of neighborhood block committees, Committees for the Defense of the Revolution, monitored and reported on their activities. More injurious still was the fact that the omnipresent state security had infiltrated the entire dissident community. No one could be sure if one of their own was a double agent.

A few weeks into my tenure I thought I was making progress when we received an invitation to attend the “old-timers” baseball game between the Cuban and Venezuelan teams. Generally the Cubans did not include the Interests Section when they extended invitations to the diplomatic corps, nor did the State Department invite Cuban diplomats to their functions. Sometimes I was pleased not to be included because I was spared from attending Fidel’s interminable speeches on July 26, the anniversary of his attack on Moncada Barracks. But I was pleased to have received this unexpected invitation. I hoped—definitely more optimistically than realistically—that perhaps this was a small gesture reciprocating my friendly round of introductory calls on Cuban officials.

Castro was coaching the Cuban old-timers, while Venezuelan president Hugo Chávez was pitching for his national team. We entered the stadium just as iron bars were descending across the entry, blocking thousands still waiting to get in. Every Cuban loves baseball; the players are excellent, and often pursued by US major league teams, which pay them salaries that are unimaginable in Cuba. Those who defect either hire a human smuggler, attempt to cross the Florida Straits in a small craft with friends or family, or quietly defect when their team is playing in another country.

With our invitation in hand we approached the section reserved for diplomats. A cross-looking official examined it, then asked what country we represented.

“Estados Unidos” (the United States), I told him.

Without any hesitation, he exclaimed, “No hay espacio.”

“If there is no space here, then where should we go?” I asked.

He simply shrugged and walked away. Maneuvering among the excited crowd, we were about to sit on a bench in the right-field section when a rather haughty man announced “No, señores, this is not the place for you.” I was beginning to wonder if there was any place for us when we spotted the international media staked out on top of the Venezuelan dugout. We squeezed in, and they didn’t mind sharing space with some cast-off diplomats.

From the roof of the dugout, we had a good view of Chávez, whose paunchy frame didn’t prevent him from getting the ball over the plate with enough zip to strike out Castro’s old-timers. We could see Fidel sitting in the Cuban dugout, chatting happily, possibly remembering the days before the revolution, when he had a fastball good enough to get him a tryout with the old Washington Senators. By the fifth inning, Fidel’s old-timers trailed the Venezuelans, until some even older old-timers, with long gray beards, began getting hits that put players on base. It turned out that these recent additions were younger players from Cuba’s national team who had donned false beards. Castro wasn’t going to lose to his protégé, Chávez, even if the game was just for fun.

We might have escaped notice had I not run into Chávez’s wife, Nancy Colmenares, an attractive peroxide blonde, who was approaching the dugout as I was leaving. We literally ended up toe-to-toe. I excused myself, beyond which there seemed to be no appropriate comment. But the incident did not escape the eyes of the ever-sensitive Cubans. The following day, the official newspaper, Granma, reported that the Cuban old-timers had won—no surprise there. Inside, however, was another article that lamented the poor security practices of the Venezuelans. This was directed at my little encounter with Colmenares. The Cubans did not like the idea that their number one enemy had somehow managed to gain entry to this friendly game. And rather than behaving, I had the nerve to call attention to myself by supposedly sidling up to and greeting the wife of their honored guest.

I told myself that this was a minor incident; surely, we would make up. Yet the auguries were not good—my first several weeks in Havana seemed to indicate that Castro was not reciprocating Clinton’s attempts to improve relations. Certainly I wasn’t going to become a trusted go-between.

From Our Woman in Havana: A Diplomat’s Chronicle of America’s Long Struggle With Castro’s Cuba by Ambassador Vicki Huddleston. Copyright © 2018 by Vicki Huddleston. Published by arrangement with The Overlook Press, Peter Mayer Publishers, Inc.