I bumped into a minor Muscovite princess on the Portobello Road last week. About 30 years old, she’d reached the generational stage of wealth where you’re happy wearing grunge. She was walking a dog, talking on her mobile, like half a dozen other girls around.

I stopped when I heard her speaking Russian. I used to live in Ukraine and Russia, 30 years ago, as the Daily Mail’s stringer, covering the break-up of the Soviet Union, when Ukraine was at the start of its independence dream. So, I mind very much what is happening today (although I’m not alone in that…). And I know that lots of Russians mind very much too, as I talk to Russians, when I meet them, whenever I can. I’ve also noticed more people speaking Russian on the streets of London today than before the Ukraine war started a few weeks ago – and I always notice people speaking Russian: there’s a wistful part of me that thinks I should probably never have left Moscow’s oil-stove grime all those years ago, in 1993, for the tragedies, adrenalin and the front pages of Sarajevo. The former Soviet bloc, for me, is the nerdy boyfriend I abandoned for someone who seemed more glamorous at the time. And then my nerdy ex became a power-crazed billionaire, his obsessions, like so many of us, only exacerbated by Covid isolation.

So when the girl had finished her phone call, I said, “I’m sorry, but are you Russian?” She blushed before saying yes. Perhaps she was expecting a diatribe about war crimes, kleptocracy, and the Oligarch-induced inflation on Prada bags and houses in the South of France and Chelsea. Instead, I asked:

“Are you OK? Are your friends and family OK?”

And it all came flooding out: “Putin is turning our country into North Korea,” she said. “Everyone’s getting out who can.”

All her friends had left Russia since the war began, she said. Of the 20 boys in her year at Moscow University, 19 have fled: Russia’s brain drain of the professional classes is staggering, and they won’t be coming back any time soon.

“They’ve come to the UK, gone to Germany, Turkey, Armenia, Georgia, the States. Wherever they have friends and they can get to,” she said. “They are all techie types. They’ve said ‘F**k this! We’re off to work for Facebook. Why would anyone drive their country’s professional future, away?”

The satirical magazine Viz ran in the late ’80s, a very prescient quiz: “How European are you?” I used to quote it to American journalists, during the Balkan wars of the ‘90s, who couldn’t understand why Europeans invaded each other. One of the questions was:

“If your neighbour’s garden is nicer than your garden, do you a) think, oh, well, my garden’s OK; b) ask your neighbour advice on how to improve your own garden; or c) move your fence 50 yards into your neighbour’s garden, calling it your garden, and shoot him when he tries to object.” Putin, like so many European strongmen before him, is answering “C! Hell yes! CCCCC!!!!!!!!” I have a theory that Covid lockdowns turned us all into distilled essences of ourselves, making sourdough, tidying drawers, or in my case, writing film scripts, running away to Italy then moving back from Scotland to Notting Hill. Putin seems to have become a distilled Russian expansionist tyrant: it looks like Ukraine was his blood-soaked lockdown project.

But Putin is fighting a war not just of territorial expansion, but cultural hegemony. He’s trying to prove that Ukraine doesn’t exist, and that any Russian-speakers living in Ukraine are desperate to be freed. Unfortunately for Putin, far too many Russian speakers in Kiev did not agree. Despite the bloodshed, the torture, the aerial and artillery bombardments, Ukraine’s citizens – whether they are more at home speaking Russian or Ukrainian – have been putting up a heroic defence.

It is Putin who has been given a bloody nose and headed for the softer targets of the industrial heartland of Donbass in Eastern Ukraine. But he still wants to cut Ukraine off from its economically crucial southern Black Sea Coast, to link Crimea to the Donbass – and to win a cultural victory he can sell to his people.

For the moment, Odessa, a jewel of both Imperial and Soviet Russia, is the next cultural icon Putin has in his sights. It’s also Ukraine’s key Black Sea port. Cruise missiles have been hitting oil refineries, depots and houses on Odessa’s outskirts the last few days. For Ukraine, Odessa is of paramount economic importance: 70% of Ukraine’s trade comes from the Black Sea, and by taking Odessa and the coast, Putin would landlock Ukraine and cripple the country financially. Taking Odessa would also help Putin drive westwards, linking up with the Russian separatists who have been sulking in Moldova’s eerie time-warp breakaway Republic of Transnistria since I reported from their communist theme park statelet 30 years ago – contradictorily full of men dressed in Cossack Imperial-style Russian military uniforms which they claimed had belonged to their grandfathers.

But Putin may fail with Odessa, for the very same reason that he failed with Kiev – because you can’t destroy in the process the cultural icon you are trying to restore to its rightful home.

The Golden Domes of Kiev/Kyiv, the birthplace of Slavic Orthodox civilisation, the heart of Kievan Rus, was what Putin initially wanted to return gloriously to Mother Russia from its cruel incarceration by Ukrainian Nazis. But Kiev’s very iconic status has saved the city from his wrath. Kiev is Orthodoxy’s Jerusalem on a hill, and even Putin can’t reduce it to biscuit crumbs like Aleppo or Mariupol.

If Putin could have driven his tanks up Kreschatyk, to the Ukrainian Parliament (past my old flat on what was then Karl Marx Street) no doubt he would have done so gladly. But his generals (the ones who are still alive, as Putin has lost seven generals in combat in the last few weeks, an extraordinary number, when you think the US army only lost 40 in the whole of the Second World War) have explained to Putin, he risked being enmired in a 21st century Stalingrad.

You don’t get to take a city the size of Kiev without hand-to-hand street fighting: modern military analysts reckon you need a ratio of 10:1 attackers to defenders. Particularly when you have a largely demotivated, corrupt army of reluctant conscripts fighting against determined resistance. And, paradoxically, the greater the destruction you wreak, the more the city’s rabbit-warren ruins become the defenders’ strongholds. The Ukrainians would almost certainly have fought a last stand from Kiev’s 1,000-year-old citadel, with the Golden Domes, the very dream Putin is trying to reclaim for Orthodox Russia, being shattered in the battle. Hard to sell that to your population.

Odessa, “Pearl of the Black Sea”, has almost the same mythic status as Kiev albeit in Tsarist and Soviet legend, not Russian Orthodoxy – just like Crimea, which Putin “annexed” in 2014. He got away with it back then because the world was in shock, and the Ukrainian army totally unprepared. Things are very different today, as Ukraine’s heroic, well-trained defence and the West’s unity and weapons supplies have shown. Odessa looks like being a very different prospect to Crimea.

I visited Odessa 30 years ago; on a forlorn morning in early March, whose grey skies perfectly reflected the city’s post-Soviet gloomy bewilderment. An 18th century imperial beauty of stucco colonnades, its Potemkin steps flowing the 174 metres down from the city to the sea, Odessa was founded by Catherine the Great in 1794 to celebrate her triumphant push to shores of the Black Sea. Its largely ethnic Russian population – a million or so today – had a traditional reputation in Old Russia for being charming, intelligent tricksters, inveterate merchants, up to every game. Back then, Odessa’s Russian charmers seemed utterly bemused to find themselves without an empire, separated from Mother Russia to boot.

Not now. These days, according to colleagues in contact with friends in Odessa recently, Odessa’s ethnic Russians prefer Ukraine to Russia. And the reason seems to be quite clear, while Putin is fighting a cultural war, the Ukrainians are fighting an ideological one: to be part of a democracy – however ramshackle – not a kleptocratic autocracy. If they don’t like Zelensky, they can vote him out. Since the war started, some Odessans are even trying to speak Ukrainian. So it seems likely Odessa’s population will put up a fight, just like they did in Kiev and Mariupol.

I’m not entirely sure, given Odessa’s heroic place in Russian Naval tradition, Putin could actually get the Black Sea fleet to fire upon Odessa’s 18th century heart. You can pound as many oil installations on the outskirts as you like, but in the end, Putin won’t be able to take Odessa without taking the centre, and that essentially requires either obliterating it, or getting the population to surrender. And few people in Ukraine have shown much sign of surrendering yet. It looks like Putin may be seen off with another bloody nose – although President Zelensky should not forget that just because the wolf has slunk away it does not mean he has left the forest. He can come back and fight another day.

But even if Putin does take Odessa, cut Ukraine off from the sea, link up with the Russia-nostalgics of Transnistria, take the Donbass, what does winning actually look like for Russia’s people? North Korea, as the Notting Hill Muscovite dog-walking princess so aptly put it. Her parents, however, are more long-suffering, stoic survivors of the old USSR. “We’ve lost our money three times already,” her parents had said. “We’ll stick it out. It’ll come round.” But for the princess and her friends – Russia’s professional future, brought up with foreign travel, Instagram and a rouble that could actually buy stuff abroad – Putin has lost them for a generation.

The author is a freelance journalist and producer of the Trojan Women Project.