On the evening of 10 November 1989, Ivan Krastev sat down with his friends in a cafeteria at Sofia University to reflect on a dying world. The day before, the Berlin Wall had been unexpectedly breached after the East German regime allowed its citizens to cross into West Berlin. Police states were collapsing in Hungary and Poland, while in Bulgaria the authoritarian leader Todor Zhivkov resigned after 35 years in power. The deadlocked topography of post-Second World War Europe was finally cracking and the Soviet order that had once seemed permanent was fading into history.

With Krastev that night was Zhelyu Zhelev, a 54-year-old philosophy professor and one of Bulgaria’s most renowned dissidents. “You young people,” he said, reclining in his chair and pointing to Krastev and the others, “you’re going to see the end of communism in your lifetime.” Nine months later, Zhelev was elected as the first non-communist president of Bulgaria.

Krastev recounts this story not only to convey the political shock that transformed Bulgaria and its people in 1989, but also because it is the last thing that he recalls about that time with any clarity. “Nineteen eighty-nine is difficult to describe,” Krastev tells me when we meet in London. “This is especially true in the case of Bulgaria because it was a historic moment that stretched over three or four weeks. Life changed so quickly and in ways that it hadn’t done for decades, which makes it hard to recall.” Most intoxicating perhaps was that not only did politics change, people did too. “Almost overnight, people had this freedom to reinvent their biographies and dream up new personas. But I was only 24 in 1989; I didn’t have much of a biography to rewrite.”

Krastev was born on 1 January 1965 in Lukovit, a small town that sits on the banks of the Zlatna Panega river in northern Bulgaria. His mother was a teacher, while his father worked on the railways before getting a degree in literature and going on to edit the country’s second largest newspaper – a prominent position within the communist nomenklatura (Krastev’s father died in a car accident in 2000). When Krastev was nine, the family moved to Sofia and in 1984 he enrolled at Sofia University, majoring in philosophy and writing a thesis on Thomas More’s Utopia (“I wanted to show that More’s book was less a vision of paradise than a strategy for colonising the new world”). Krastev has fond memories of his student days, especially in his final year when the Wall came down. “The only thing better than studying in a free university is studying in a newly liberated one.”

Graduating in 1990, and after publishing a book of poems called Reading in the Darkness, Krastev became an adviser to Zhelev and was tasked with figuring out how to make the president of a small, relatively unknown post-communist state a recognised player within the cabinets and chancelleries of Europe. According to his friend, the writer and Oxford historian Timothy Garton Ash, Krastev had an idea. Perhaps the most infamous episode in modern Bulgarian history was the assassination of the dissident Georgi Markov in London in 1978. An activist and BBC World Service broadcaster, Markov had been living in exile in London since 1971. One morning, as he was waiting for a bus on Waterloo Bridge, Markov felt a sharp sting in his leg. He did not realise it at the time, but he had been shot with a ricin-loaded pellet using a modified umbrella gun, likely by an agent of the Bulgarian security service (though no suspect was charged). Markov died four days later.

Sensing that this story was the only one many people knew about communist Bulgaria, Krastev’s plan to ensure his boss got noticed was simple: he advised that he should carry a black umbrella around with him. Zhelev politely declined the advice of his young counsellor – “but it tells you something about the spirit of the times,” Krastev says. The tale also reveals something about Krastev himself: he is original, astute and darkly mischievous.

Krastev moved to St Antony’s College, Oxford – an intellectual redoubt of Anglophone liberalism – in 1991, where he studied under Garton Ash. He was part of a cohort of students, including the American historian Timothy Snyder and the Canadian journalist turned minister of foreign affairs Chrystia Freeland, who would become some of the most fluent apostles of post-Cold War liberalism (the Washington Post columnist Anne Applebaum attended the same programme a few years earlier). Garton Ash told me that along with Snyder, “Ivan was one of the most outstanding students of that group. Everyone in that class was inspired by what happened in 1989.”

Today Krastev has a cooler, more sceptical approach to thinking about history and politics than many of his peers and he exudes none of their liberal crusaderism. From his berth at the Institute for Human Sciences in Vienna, where he is chairman of the Centre for Liberal Strategies, Krastev has cast his gaze across European politics and wonders if the liberal triumph of 1989 was an illusion and whether liberals have misinterpreted the present and the nature of the post-Cold War period.

“How liberalism ended up the victim of its heralded success in the Cold War” is the subject of his latest book, The Light that Failed, which he co-authored with the NYU law professor Stephen Holmes. At a time of democratic backsliding the book is one of the freshest and most insightful takes on liberalism’s “crisis of self-doubt”.

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When the Berlin Wall was toppled there were only 16 border fences in the world; now there are more than 60, either completed or under construction. And while liberal democracy’s post-1989 afterglow has been dulled by the illiberalism of right-wing populists such as Viktor Orbán in Hungary and Jaroslaw Kaczynski in Poland, it has also faded in the shadow of an ever-rising China.

For Krastev and Holmes, 1989 heralded a 30-year “Age of Imitation” in which the newly liberated nations of central and eastern Europe endeavoured to mimic the liberal democracies of the West. The desire to shed their pasts and be “normal”, combined with the historical imperative to become part of the new US-led unipolar order, pushed the former Soviet states to try to become like their Western neighbours.

Krastev, who speaks so quietly as to be almost inaudible, remembers the first time he “discovered the West”. In 1990, while travelling to a seminar in Dubrovnik in Croatia, he stopped off in Belgrade. “I was shocked by the books and jazz clubs that were there, and only a few hundred kilometres from Bulgaria! It was like moving from black and white into a colour movie. I later travelled to Paris and London, but nothing will compare to those first few hours in Belgrade.”

Krastev and Holmes locate the populist xenophobia and reactionary nativism in central and eastern Europe in the sense of betrayal felt by elites who imitated the West. Krastev stresses to me that after 1989, former anti-communist liberals such as Orbán “believed in the West but it was the Cold War West – one that embraced tradition, family values and national sovereignty”. (Today Orbán believes himself to be the defender of Christian Europe.)

But after the fall of the Berlin Wall, when Western societies underwent their own social and economic transformations, these values either disappeared or were overridden by globalisation. “It’s difficult to imitate a political model that is changing all the time. It creates an idea that you’ve been cheated, especially when you’re constantly being told that there is no alternative to liberal democracy; 1989 completely underestimated the psychological need for people to have political and economic alternatives or even the illusion of having alternatives.”

But Krastev says that exponents of “illiberal democracy” such as Orbán and Kaczynski, as well as Vladimir Putin in Russia, now see themselves as the true inheritors of the transformations of 1989. Fusing anxieties of demographic implosion with ethno-nationalism and big-state conservatism, they claim to represent real Europeans and argue that if the West wants to save itself it will now have to imitate the East. “Nineteen eighty-nine was the revolution that everyone appropriated,” Krastev tells me. “Liberals, leftists and conservatives all fell in love with this year because it reinforced certain assumptions each of them had about the world. For liberals, 1989 was the moment when liberalism discovered its revolutionary potential. Classical Marxists were optimistic because it provided an opportunity to reinvent a non-Stalinist left. For conservatives it was about the failures of the planned economy. And nationalists such as Kaczynski felt on the winning side because they had been strongly anti-communist. Nationalism was a much more important part of the 1989 epic than liberals have been ready to admit.”

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Can the right-wing populist advance be reversed? Last month, Orbán’s Fidesz Party sustained heavy losses in local elections, while the liberal political scientist Gergely Karacsony ousted the ruling incumbent to become mayor of Budapest. “Anything can be reversed!” Krastev exclaims, his voice rising for the first time. He alludes to Albert Hirschman’s classic study Shifting Involvements (1982), in which the economic theorist showed how and why frustrations in our private lives lead us to public engagement and how frustrations with public engagement eventually lead us back to our private lives. “I believe these cycles also happen in politics,” Krastev says. “People got disappointed with the liberal status quo and reacted against it, but populism is also disappointing people. In both Hungary and Poland the opposition is winning in the big cities. Indeed, the major political division these days is not between East and West but between the urban centres and the countryside.” Ultimately, as he and Holmes argue at the end of their book, once it jettisons aspirations to global hegemony, liberalism will still remain “the political idea most at home in the 21st century”.

It seems fitting to be speaking to Krastev about 1989 at a time of global revolt, as uprisings take off in Hong Kong, Chile, Lebanon and other parts of the world. In their moral outrage these revolts have a passing resemblance to the liberal revolutions of 1989 that inspired the young Ivan Krastev. “Their legitimacy comes from their spontaneity because suddenly people are in the streets. It’s not the same sorts of people with the same ideological affinities. You don’t really know who is protesting. In that sense, they are the people from nowhere. Nobody organised them. They just come to the public square and say: enough!”