In Europe, few people have had as much impact on tech governance and the integration of the Baltic countries as Toomas Hendrik Ilves, professor of international affairs, journalist, writer, ambassador, foreign minister and former president of Estonia. His personality, his experience and his iconic bowtie made him a well-known figure on the political stage. From time to time, he shares DG MEME’s memes on his very active Twitter (currently known as X) account, so one day I decided to reach out to him and ask for an interview. And he kindly obliged.
I meet him in his office in Tallinn, in the Kastellaani detachment of the beautiful presidential Palace of Kadriorg. The day is warm and dry, as pleasant as only Estonian summers can be. One of his assistants lets me into the building and we shake hands with mutual curiosity. The down-to-earth approach of northern politicians always amazes me: “Please, take a seat, I just finished recording a podcast in which we’re trying to explain the EU to the US. What can I do for you?”
Ilves has been out of politics for almost a decade but he doesn’t miss a beat of what is happening in the world: “I am addicted to news in ways that are probably unhealthy. It’s a habit that I started when I worked as a journalist for Radio Free Europe (RFE) and the coming of the internet only made it worse.” I promise him I will focus on his life and there will be no questions about digital Estonia or cybersecurity, “Everybody asks you those.” He smiles: “But they are indeed intimately related to my life.”
Ilves was born in Stockholm in 1953, to Estonian parents who had escaped the Soviet advance in 1944; in the chaos of the Nazi retreat and the returning Red Army, around 70,000 Estonians fled west in what is known as the Great Escape. They expected to be away only briefly.
One of them was Toomas’ father, Endel, who reached Sweden almost by accident: “One day he was walking to the bus station when two armed and drunk men forced him to the harbour and made him row them out to a bigger boat anchored offshore. The boat’s captain turned out to be his cousin. ‘Come on, let’s go. We will go to Sweden for three weeks and then everything will be fine. The Brits will come and tell the Russians to go back’. This was not an unreasonable fantasy in the fog of war.”
Unfortunately for Estonians, that’s not how history went. Ilves’ parents stayed, studied and met in Stockholm. Endel became an engineer, Irene earned a master’s degree in Slavic studies and another in library science. His parents didn’t pass Estonian culture on to their children in any particular way, as they assumed they would never go back to their country: “It was mostly the language, we spoke Estonian at home, with the usual limitations of a domestic language: it wasn’t highly literary, I acquired that only later.”
His parents vaguely mentioned Hans Rebane, a maternal great-uncle who was once minister of foreign affairs of Estonia during Estonia’s first period of independence (1918–40). “Later, I discovered there were some parallels between the two of us: when I was ambassador in the US, I had to follow the purchase and restoration of the current Estonian embassy, one of the worst experiences of my life. Later, I found out that my great-uncle had done the same in Helsinki, and when he was asked to create a new embassy in Riga, he refused. It has nothing to do with diplomacy; it’s only about contracts and planning.”
The Ilves family relocated to the US in 1957, settling down in Leonia, “The Athens of New Jersey”, a small commuter town that after 1890 attracted prominent figures in culture and science. “I realized only later that it was a stimulating environment, to me it looked just normal. The school system was really good; people moved there to put kids in that school”.
And even at home there was no shortage of intellectual stimulation: “My family read books, on Saturdays they would drive me to the library and I would take out lots of books and then I read them, and forgot to bring them back, then I had to pay fines. I never stopped reading; my library today counts around 20,000 books.”
As a child, Ilves quickly understood what it means to come from an occupied country: “We had children from everywhere in our class, and so the teacher would ask us to show where we were from on the map. I said, ‘I am from Estonia,’ and pointed at it. And they told me: ‘But that’s Russia’. I said: ‘No, it’s Estonia!’. It was traumatic, I was not even on the map!”
Stronger ties to his home country came from the Estonian boy scouts, which had regional, national and international groups. Here Ilves made lifelong connections, for example with stand-up comedian Andrus Valvur, with whom he co-hosts the podcast Continental Rift: “Unlike most Americans, I ended up having a lot of international friends. Estonian scouts were very patriotic; I guess in the scout masters’ fantasies they were training the Estonian guerrilla of the future. And it was rough, I learned to shoot a rifle when I was nine, and not a small one, a .30-30, my shoulder had bruises for weeks.”
The founding of Forest University (Metsaülikool) in 1967 was formative for Ilves. Looking for a way to preserve their heritage, a group of Estonian Boy Scouts in exile purchased and developed the wilderness campground of Kotkajärve (“Eagles’ Lake”), in Ontario, Canada, turning it into a place for political debates and cultural workshops entirely in the Estonian language. “That was where I discovered contemporary Estonian literature, which is literature produced in occupied Estonia and written under censorship. And I understood that the problems they were talking about, the obliteration of a language and the death of a culture, were extremely important. Kundera mentions this in many of his essays, the Czech intellectuals called it estonizace, estonification, which means the removal of the culture of a small country by the Soviet Union. They were afraid it would happen in Czechoslovakia too.”
During high school, Ilves met Christine Cummings, a teacher who was doing her PhD in math education. She selected the best students in the class and taught them how to program and Ilves was among them. After all, his surname means lynx in Estonian. “The teletype machine was connected with a big telephone modem to a mainframe fifty kilometers away. And we learned BASIC. Later on, I realized that BASIC was only six months old and we were already using it in school.”
The teacher and the pupil remained in touch over the years: “As minister of foreign affairs and president I would often go back to New York for the United Nations General Assembly and I would tell her I was coming. One year, I even managed to meet her in our school. This was after Estonia became known in the world also because of Skype. If she had never taught me how to program, I would have never come up with the idea of digital Estonia.”
Besides the fascination for science and literature, Ilves discovered his passion for music, which he inherited from his father. “He loved contemporary music. One day he took me to see Frank Zappa & The Mothers of Invention at the Bleecker Street Theater, a small venue with maybe 250 seats. It was pretty wild, Frank Zappa was throwing meat at the audience.”
Obama mentioned in a speech that Ilves knew Bruce Springsteen before he had his first record. “That’s not true, Obama made that up. I saw Bruce Springsteen in some concerts, because he was known in New Jersey, but I didn’t know him personally. When Obama shared that made-up anecdote, I knew it was going to haunt me for the rest of my life.”
At university, Ilves studied experimental psychology: “The name might be confusing, but it was not Freud, it had nothing to do with people. It was about approaching philosophical problems, such as perception and cognition, with science. And that was very interesting to me.”
He graduated from Columbia University for his bachelor’s degree and the University of Pennsylvania for his master’s, both leading centres for vision research at the time. During his studies, he got thunderstruck by Thomas Pynchon’s Gravity’s Rainbow (“The greatest book ever written”), a dark, paranoid, anti-technocratic novel that presents academia as complicit in the war industry and mass control. “I understood I was at the university only because I had very high grades. But I couldn’t see myself becoming a professor of vision, so I graduated and then I took a year off to hitch-hike through America”.
It was 1977. Ilves, twenty-five years old, hitch-hiked by himself on an almost straight line to the West, from Leonia to Madison, Wisconsin and Boulder, Colorado where he had some friends. Then he took a bus to San Francisco, to visit some relatives, and hitch-hiked north, towards the state of Washington. “It was a bit scary, because in the Santa Rosa area there was a serial killer who was torturing and killing hitch-hikers.
Anyway, I was picked up by a guy who had just gotten out of jail, three years for smuggling marijuana; and he told me he was thinking of going to work for the forest service as a firefighter and make a lot of money. Once I arrived in Seattle, I decided to sign up for that job. And as I was the only one who had immediate availability, they chose me, even if I had no experience. So, I spent a season fighting forest fires and they proposed me to come back as team leader the next summer.”
In 1980, Ilves married his first wife Merry Bullock and followed her to Vancouver, where she got a position as a professor of psychology. “Jobwise, what I was doing there was not really interesting, but I read a lot to keep myself busy. And I got even closer to Estonian modern literature and because of that I read a lot about the Soviet Union and I started writing some articles about the occupation. And I taught Estonian literature at Simon Fraser University (Burnaby, Canada, ed)”.
Ilves became known academically and eventually, in 1984, he got a job offer from Radio Free Europe: “They had just gotten a huge boost in funding. They had a new research department and they were looking for an Estonian who could write in English. The position was in Munich, which was very convenient for me, as my brother lived in Den Haag”.
The two brothers travelled together for a few weeks, first reaching Vienna and then deciding to continue to communist Hungary: “We got a quick visa and entered Hungary on May 1. We didn’t know anyone there and it was really hard to speak with the local people. Then I had this idea to visit the Finno-Ugric department of the university and there we met the head of the department (Gabor Berecki, ed), who could speak Estonian fluently, also because his wife was Estonian. We had a great time.”
The end of the Eighties was a time of change on the local and global stage: Luukas, Ilves’ first son, was born in 1987; and protests in the Soviet Union became more structured, especially in the Baltic states, with the beginning of the Singing Revolution. “There was a lot of debate about my articles on Estonian struggles. I was even summoned by George Urban, the director of RFE, a Hungarian-born überbrit, who had been Thatcher’s foreign policy advisor. He told me: ‘You write well, but Estonia will never be independent. Leave that topic and specialize in anti-terrorism, it’s a growing field.’ But I declined.”
Ilves’ articles reached a wider audience after he disclosed that Soviet authorities were rounding up Estonians in the streets and sending them to Chernobyl to clean up. “I was following the Estonian press, it was slightly freer than the Moscow one, it was so local that they thought nobody was going to read that. And I found the article that mentioned that fact. In Radio Free Europe they did not believe me initially, but eventually the New York Times picked up my article and asked about it during a press conference at the International Atomic Energy Agency in Vienna. And it caused a big stir; the Soviets were barely admitting that something had happened in Chernobyl. After that, in 1988, I was asked to head the Estonian services of Radio Free Europe. And that was when things started happening.”
Ilves developed his network of informants, also thanks to a technical trick: “I managed to smuggle an okean radio out of the Soviet Union, which was able to receive Soviet Union FM and Estonian radio, something impossible to western radios. And I shipped that to Finland, because from there we could receive the signal better. And whenever there was something interesting going on, my contact there would then place the radio next to the phone and I could listen to the Estonian radio from Munich and comment on the news on the same day, before they were even printed in newspapers!”
The communication between the West and Estonia was not always easy. “I had friends in Finland who were entering Estonia often, mostly for its cheap drinks. And I’d ask them: ‘Can you take this for me?’ and they would send things out and carry return messages to me. It wasn’t easy to organise but we managed. That’s how I got in touch with a writer and filmmaker called Lennart Meri, who got out to Finland relatively often. He would then become the first president of post-Soviet Estonia.”
After Chernobyl, protests became more common in the Soviet Union and in its satellite countries. The Baltic states organised ‘The Baltic Way’, a peaceful political demonstration in which two million people from Estonia, Latvia and Lithuania formed a 600-kilometer human chain to demand independence from the Soviet Union. “It was a big thing, we didn’t have anybody there, because the authorities wouldn’t allow it. But we were broadcasting about it.”
From 1987, Gorbachev implemented the policies of perestroika (“restructuring”) and Glasnost (“openness”), trying to loosen Soviet control over information so people could discuss problems that had previously been hidden. Ilves decided to call the bluff and asked his boss for permission to go to Estonia. “I was young, back then. I was in my early thirties, all the other chief editors were in their fifties. I managed to be persuasive but it still took them two months to approve my idea. Eventually I wrote to the foreign minister of the Estonian Soviet Socialist Republic requesting a visa. The Commies told me: ‘Call this number, go see this guy and bring your documents; and a present, he likes drinking’. I brought an expensive bottle of Cognac and, in November 1988, I was allowed to enter Estonia, the first Radio Free Europe employee to do that legally.”
Ilves already visited Estonia briefly in 1984 but the situation was very different: “Back then I was a tourist, a way for the Soviet Union to earn some hard currency. But this time, I was the enemy, I was followed everywhere and I couldn’t leave Tallinn. Later on, after the collapse of the Soviet Union, I discovered some documents from the Moscow Central Committee in which they were complaining that Estonia SSR let me in. In fact, they let me in once, but then they didn’t let me in again for a while.”
Despite his Soviet guardian angels, during his visit Ilves managed to reconnect with his country. “I gave a lecture at the Writers’ Union and I finally met in person the people who would later become the leaders of independent Estonia. People in Estonia knew me because I was on the radio, and I knew them through their letters and messages.”
One year later the Berlin Wall fell and two years after that the Soviet Union followed suit. “All I could do was watching it on TV. No one imagined it would happen so quickly, not even the CIA. It’s like when Stefan Zweig, a writer I love, describes the summer of 1914: everything looked perfect, the future looked bright and then bam! World War I. I would say the attitude in Estonia was: ‘It will fall because everything is collapsing, but we don’t know when’. I have the same feeling about Russia now; without fuel they can’t go on.”
This unexpected turn of events caused a lot of debates in the West: “They did not really want to think of the Soviet Union collapsing: just a couple of weeks after the putsch in Moscow in 1991 President Bush senior warned against ‘suicidal nationalism’. In Europe they had been telling us for forty years: ‘Become liberal democracies and you can join us’. And there we were, we rebuilt democracy. But they couldn’t just let us in as it was in the past.”
In fact, in 1994 Wolfgang Schäuble and Karl Lamers proposed the creation of a Core Europe: a tightly integrated Franco-German-Benelux nucleus that would move ahead with political union while the wider EU expanded around it. “It was another way to keep Eastern Europeans in the second class, an idea which persisted I would say until 2022, when they discovered our fears over Russia were correct.”
Meanwhile, Ilves and Meri remained in contact and Ilves started writing speeches for him: Meri became minister of foreign affairs of the reborn Republic of Estonia and invited Ilves to become Estonian ambassador to the United States: “Meri kept asking me but I was not sure, it meant giving up a very well-paid job and renouncing my American citizenship. Then we had this meeting with him and Marju Lauristin, one of Estonia’s main intellectuals; and she told me: ‘What are you still doing there in the West? Enough, give it up, we need you here.’” Unfortunately, the time allotted for the interview was over. But President Ilves was kind enough to grant me another meeting to continue our conversation. Keep reading about Ilves’ life, his work on digital Estonia and his presidency in Born to run (and return).