A former spy who spent half a century cutting a ruthless path to global dominance, Vladimir Putin strutted confidently into his one and only meeting with Volodymyr Zelenskyy.
His Ukrainian opponent was, after all, a comedic actor whose only political experience was playing a president on television.
He was also ridiculously young — practically a millennial.
Both men may have been born in the Soviet Union, but only Mr Putin was old enough to remember its implosion. And only Mr Putin was determined to recover what he believed was lost.
And so Mr Putin arrived for their 2019 meeting in Paris, chaperoned by Angela Merkel and Emmanuel Macron, with his usual pomp and ceremony.
As always, he was late so he could make an entrance.
He rolled up to the Elysee Palace in an Aurus Senat, a seven-tonne Russian limousine often described as a counterfeit Rolls Royce.
Mr Zelenskyy, meanwhile, had arrived a little early in a mini-van.
The then 41-year-old had a lot at stake.
Six months after his landslide election victory, he was under intense pressure to get Russia out of rebel-held territory in Ukraine’s east.
And after eight hours, the four leaders walked out of the room with an agreement: Ukraine and Russia would try to honour a five-year-old ceasefire that had, until then, been largely ignored.
In a post-summit press conference, Mr Putin projected faint optimism, saying a “thaw” had occurred in frosty relations between the two neighbours.
But Mr Zelenskyy spoke with honesty.
“I would have liked to have seen more,” he said.
“It is vital for Ukraine to restore control of the entire length of its border.”
It was the young Ukrainian’s first flash of defiance to the Goliath at the other end of the table.
Two years later, Mr Putin would order Russian tanks and troops deep into Ukrainian territory.
But just as he did in the gilded meeting hall in Paris, Mr Zelenskyy defied expectations.
With the charisma of a TV star, the wardrobe of an action hero, and the social media strategy of a savvy influencer, Mr Zelenskyy is fighting — and winning — the information war.
And Mr Putin, once considered the master of propaganda, is finding himself outmatched.
As Mr Putin sent the full force of the Russian military across the border in late February, Mr Zelenskyy knew the odds were not in his favour.
Ukraine spent $6.3 billion on defence last year. Russia spent $62 billion.
Mr Zelenskyy had just over 1 million active troops and reservists at the ready. Mr Putin had 2.9 million.
But wars are not only fought and won on the battlefield.
If he was going to galvanise support from the West in the form of sanctions and military intelligence and weaponry, he needed to win the information war.
“Ukraine isn’t just winning the battle for hearts and minds online, it has already won,” US defence expert PW Singer wrote in Politico.
“And now it’s too late for Russia to change the narrative.”
Dressed in a khaki T-shirt and a hoodie, Mr Zelenskyy has stood his ground in Ukraine’s capital, even as it turned into a war zone.
“I am here,” he said in a video viewed 3 million times in its first hour on Instagram.
“We will protect our country. Our weapon is truth. And the truth is that it is our land. Our country. Our children. And we will protect it. That is it. That’s what I wanted to tell you. Glory to Ukraine.”
Mr Zelenskyy’s government has adopted a modern and relentless communication strategy.
They have bombarded Russia’s official social media accounts with sassy memes, packaged tales of heroism and tragedy to go viral, and deployed the President to talk to everyone from the United States Congress to actors Ashton Kutcher and Mila Kunis.
Meanwhile, Mr Putin has reached for a familiar playbook, according to Bart Cammaerts, a professor of communications at the London School of Economics.
“Violent repression, censorship, coercion, obfuscation and cynical distortions, presenting an alternate reality befitting the Russian worldview and interests, mostly geared towards shoring up internal legitimacy,” he said.
While this strategy might be working within Russia, experts say Mr Putin appears to have vastly miscalculated on three key issues.
Not only did he overestimate Russia’s military power, he greatly underestimated Ukraine’s determination and the West’s support for his rival Mr Zelenskyy.
So how did a man once widely seen as a master chess player thinking several steps ahead of the rest of the world find himself in this situation?
For years, Mr Putin’s fixation with the past served him well.
While other world leaders thought in terms of election cycles, he was trying to restore Russia to an ancient glory.
When the Soviet Union collapsed in 1991, Russian officials were quick to replace the paintings of Communist leaders that adorned their offices with portraits of the new president, Boris Yeltsin.
But a young Mr Putin, working as mayor Anatoly Sobchak’s personal assistant, chose the all-powerful tsar Peter the Great for the new decor instead.
A visionary ruler who transformed Russia from an isolated outpost into a sizeable world power seems a fitting role model for a modern leader coming of age as the Soviet Union battled the US for supremacy.
But Peter the Great built his legacy with an unrelenting, battle-ready approach, hell-bent on delivering Russia a “window to Europe” via the Black Sea.
It’s said that both Peter and his successor, Catherine the Great — who overthrew her husband Peter III and continued to modernise Russia while ruthlessly expanding its territory — still adorn Mr Putin’s office walls today.
The Russian President has echoed his predecessors’ aspirations to ensure the rest of the world respects his motherland, at any cost.
In 2005, he famously described the fall of the Soviet Union as “the greatest geopolitical catastrophe of the century”, and in the years since he has tiptoed towards an all-out mission to revive those glory days.
“He goes to bed at night thinking of Peter the Great and he wakes up thinking of Stalin,” former US intelligence committee chair Mike Rogers observed in 2014, while Putin’s troops were annexing Crimea just as Catherine the Great had done in 1783.
Many have played down the comparisons in recent years, but Mr Putin’s speech last week, in which he called Russians who do not support the war “scum and traitors” and advocated a “self-purification” of the nation, has been described as his “most Stalinesque” diatribe yet.