War has changed Zelensky – but now is the time to transform again

“The best salesman in history.” This was what Donald Trump once called Volodymyr Zelensky because of the amount of aid the US has given Ukraine.

Whether or not a fair comparison, Zelensky’s role in keeping his country in the spotlight and convincing allies to invest has certainly been crucial for Ukraine’s fight.

His transformation from prime-time comedian to wartime president has long been cast – it dates back to 2022 when he decided to remain in Kyiv as Russian troops closed in. That decision meant Ukraine would go on to defend itself to this day.

In the years since, I’ve stood across from him in person dozens of times, and Zelensky now casts a more authoritative, perhaps battle-hardened figure, moulded partly by his increased isolation on the international stage.

But with the unpredictability of Trump’s second term – not least following the pair’s Oval Office bust-up in February – Zelensky may now have to transform again.

Politically it is no longer a story of oppressor versus oppressed. Rather, it is muddied by the dual challenge of voicing an appetite for peace whilst protecting his country’s interests.

But is a man used to having so much authority at home and being so influential abroad really going to stage a second big transformation, shifting his focus to Trump-era diplomacy? Or will he decide the best way of standing up for Ukraine is to yield little?

Before Trump’s chapter two began, Ukraine’s leader had effectively lobbied for western support. He appealed for air defences, tanks, rockets and fighter jets, with nations such as Germany hesitating over fears of the war escalating, before yielding to his requests.

His message was rigid and he was successful in procuring support.

“Zelensky was very clever and calculated in the early days of the war,” says Ed Arnold from defence and security think tank, Royal United Services Institute (Rusi).

His decision go to the Munich security conference two weeks before the invasion, despite being advised that this would be a security risk, was pivotal, argues Mr Arnold.

“It personalised support to Ukraine within the minds of people who personally attended.”

Serhiy Leshchenko, an advisor to Zelensky’s office, explains: “We have to be visible to the world. If public opinion is on Ukraine’s side, there is a better chance to get help from the international community.”

Leshchenko points to Zelensky’s daily video addresses, which he has created since start of the invasion. “It’s unusual to be so open.”

Ukraine’s victory in the battle of Kyiv cemented Zelensky as a symbol of the country’s survival, and boosted his case for continued military aid from western allies.

Later in 2022, Zelensky was able to demonstrate the difference their supplies were making when swathes of Ukrainian territory, including the city of Kherson, were liberated. He had initial success with European allies.

“They are invested in Zelensky personally and Ukraine,” says Mr Arnold. “He’s gone through four UK prime ministers since the start of the war … and they’ve all signed new declarations with Ukraine, again through Zelensky.

“He’s been able to weather the changes in national politics within Europe throughout his tenure.”

But when further successes failed to materialise, Zelensky’s message did not change – and as time went on, this would be to his detriment.

After Ukraine’s failed counter-offensive in the summer of 2023, for example, the merits of supporting Kyiv were increasingly questioned by an influential minority of US Republicans and pleas were starting to be passed over in some quarters.

Maria Zolkina, head of regional security and conflict studies at the Democratic Initiatives Foundation, a Kyiv-based think tank, believes Zelensky is partly responsible.

“He and his close circle relied on the logic that they must always be demanding when speaking with their partners – pushing the argument that Ukraine simply needs something. That worked really well during 2022, but with the US and others this kind of messaging stopped working in 2023,” she argues.

“But his diplomacy really didn’t adjust quickly enough.”

On 27 September 2024, in a lobby in New York, things truly changed for Ukraine. Only the driving force was not approaching Russian armour but the political reincarnation of Ukraine’s biggest ally: the US.

On that day, just over a month before the US Presidential election, Zelensky had a last minute meeting with Trump in Trump Tower.

Tensions between the pair had heightened before this meeting: Zelensky had claimed a few days earlier that Trump didn’t “really know how to end the war”, after he asserted he could do it in “one day”.

After the Trump Tower meeting, the two men emerged looking awkward.

Despite announcing a “common view” of wanting to end the war, their body language suggested a lack of chemistry.

The pair would not meet again until five months later in the Oval Office, where their now famous encounter would be a diplomatic disaster for Kyiv.

“Trump should have liked him,” says Vadym Prystaiko, who was present when the pair first met after Zelensky’s election win in 2019. “Zelensky saw Trump as more or less as himself, as a media guy who moved into politics, who was anti-establishment,” he says.

Mr Prystaiko was Ukraine’s ambassador to the UK, before he was sacked in 2023. Kyiv gave no official reason for the dismissal, but it came after Mr Prystaiko criticised Zelensky’s response to a row over gratitude for British military aid. He said there had been a “little bit of sarcasm” in his president’s response, which he believed was “unhealthy”.

“Zelensky has never been a diplomat,” Mr Prystaiko adds. “He has never been a usual political leader who kisses babies and shakes hands.”

“The relationship with Trump is like a rollercoaster,” says Volodymyr Fesenko, director at the Pento Center for Political Studies. “Sometimes there is constructive cooperation, and then, all of a sudden, some kind of crisis appears.”

Then there is their war of words. Trump has blamed Zelensky for starting the war, calling him a “dictator”, while Ukraine’s leader accused his US counterpart of “living in a Russian disinformation space”.

While Mr Fesenko believes Zelensky is continually changing tactics to find a working relationship with Washington, Ms Zolkina believes the issues go deeper.

“There is a triangle between the US administration, the Kremlin and Kyiv,” she claims. “Ukraine is considered to be a weaker part of this triangle. For Trump, Zelensky is not in the same league, and that’s the problem.”

When it came to the now infamous Oval Office meeting with Trump and his Vice President JD Vance, this was the first time I’d seen Zelensky seemingly run out of political rope as he was accused of “not showing enough gratitude” and “playing with World War Three”.

His defensive body language, the folding of his arms for example, also seemed new.

Zelensky has always appeared comfortable hosting or visiting other leaders. He is at ease on a stage and often injects timely humour — but this was different.

A mineral agreement, in which Zelensky had originally suggested trading a portion of Ukraine’s mineral resource wealth for continued military aid, was never signed, and has since evolved into a less favourable proposal for Kyiv.

The US would also briefly pause its military aid and intelligence sharing to ensure Ukraine danced to its tune.

But the official view from some is that the Oval Office meeting was not a calamity.

“Nobody took it as the end of something,” claims Ihor Brusylo, the deputy head of the Presidential Office, who travelled to the White House with Zelensky. “We discussed how to move forward. It was not a disaster.”

When the US National Security Advisor Mike Waltz told them the meeting was over, “we just shrugged our shoulders and decided to go back to the hotel,” he recalls.

“My presumption is that on a personal level, they [Trump and Zelensky] get on well,” he adds. “They understand each other better, and are frank and honest.”

Whatever the truth about their relationship behind closed doors, there have been signs of a willingness to bend from Zelensky since that meeting – European allies are said to have convinced him to subsequently take a more compliant tone, because of the inescapable truth that they, and Ukraine, still need the US to combat an aggressive Russia.

Yet others argue more bend still is needed.

“The war changes everyone, it has changed us all in some sense. But I don’t think fundamentally Zelensky has changed – for good or bad in some instances,” says Olga Onuch, professor of Comparative and Ukrainian Politics at the University of Manchester.

“It is very clear that certain actors have decided it’s difficult to negotiate with Zelensky. Why? Because he has red lines that he is sticking to.”

Mr Brusylo agrees. “It is very difficult to bend Zelensky,” he says. “It’s like watching a spring, the more you press, the bigger the pushback.”

And yet whenever Ukraine is attacked, politically or diplomatically, increased political unity follows. The Oval Office clash was no exception, as Zelensky’s popularity rating soared to around 70%.

“Zelensky is very powerful, and his authority is made up of himself and a certain circle of people,” argues Ms Zolkina.

Orysia Lutsevych, head of the Ukraine Forum at Chatham House says it’s interesting how Ukrainians rallied around Zelensky after the Oval Office, almost like they took it as a personal insult of Ukrainian statehood.

“People rally around him, what he represents and how he behaves”.

Mr Prystaiko argues if the Americans wanted him to be replaced “they’ve shot themselves in the foot as he might easily be re-elected”.

Some political experts, like Ms Zolkina, do not think this is a certainty. “I don’t think he understands that this boost is a direct reaction to what Trump is doing, not his personal position,” she says.

“He has pretty strong political ambitions for a second term, and is pretty politically egocentric, as all leaders are at his level.”

Prof Onuch does not think that pursuit of political power alone motivates Zelensky. “[He is] much more of a careful and considered and tactical political operator than people give him credit for”.

Still, imagining a Zelensky second term can be difficult, simply because of the sheer demands of the job. Even post-war challenges would be considerable.

For now, Mr Arnold suspects that an exhausted Zelensky would not want to stand again and suggests that he may want a way out from at least the frontline politics.

As for the near-term, Zelensky cannot afford another Oval Office. So, given that Trump is a keen player, will Ukraine’s leader ever join him for a round of golf?

“He is a quick learner,” says his Mr Brusylo. “When there is a need to play golf, I’m sure he will tackle this task.”

Top picture credit: Getty Images

Additional reporting by Hanna Chornous and Vicky Riddell

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