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

Volodymyr Zelensky, the President of Ukraine, was once labeled “the best salesman in history” by Donald Trump, alluding to the significant amount of US aid directed to Ukraine. Regardless of the aptness of this comparison, Zelensky’s efforts to maintain international attention on his nation and persuade allies to provide support have been indispensable to Ukraine’s defense.

Zelensky’s transition from a comedian to a wartime president has been well-documented since 2022, marked by his pivotal decision to remain in Kyiv as Russian forces advanced. This choice galvanized Ukrainian resistance and defined his leadership. Having observed him numerous times since then, Zelensky now projects a more commanding and resolute persona, shaped partly by increasing international pressures. However, with the uncertainties surrounding a potential second Trump era, particularly after their tense Oval Office meeting, Zelensky might need to undergo another diplomatic transformation.

Prior to the resurgence of Trump’s influence, President Zelensky effectively advocated for western support. His appeals for air defense systems, tanks, rockets, and fighter jets faced initial reluctance, particularly from nations like Germany concerned about escalating the war. Ultimately, these nations conceded to his requests. His consistent message proved successful in procuring international support.

Ed Arnold, from the Royal United Services Institute (Rusi), notes, “Zelensky was notably strategic and calculated in the initial phases of the conflict.”

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Arnold highlights Zelensky’s decision to attend the Munich Security Conference shortly before the invasion, despite security advisories against it, as being particularly critical. “It personalized international support for Ukraine among key global leaders.”

Serhiy Leshchenko, an advisor to Zelensky’s office, explained, “We have to maintain visibility globally. If public sentiment favors Ukraine, there is a greater likelihood of securing assistance from the international community.”

Leshchenko points to Zelensky’s daily video addresses, a practice initiated at the onset of the invasion. “Such openness is unprecedented.”

Ukraine’s victory in the battle for Kyiv solidified Zelensky’s image as a symbol of national survival, reinforcing the argument for sustained military aid from western allies.

Later in 2022, Zelensky effectively showcased the impact of these supplies when significant Ukrainian territories, including Kherson, were liberated. He initially found success with European allies.

“They have a personal investment in Zelensky and Ukraine,” Arnold stated. “He has navigated through four UK prime ministers since the war began, and each has signed renewed declarations with Ukraine, invariably through Zelensky.”

“He has successfully navigated shifts in national politics within Europe throughout his tenure.”

However, as further triumphs did not materialize, Zelensky’s messaging remained unchanged, which eventually proved detrimental.

Following Ukraine’s unsuccessful counter-offensive in the summer of 2023, the value of supporting Kyiv faced increasing scrutiny from a notable minority of US Republicans, and appeals began to be disregarded in some circles.

Maria Zolkina, head of regional security and conflict studies at the Democratic Initiatives Foundation in Kyiv, suggests Zelensky bears partial responsibility.

“He and his inner circle operated on the principle of constant demands when engaging with partners, consistently arguing Ukraine’s need for assistance. This approach was effective in 2022, but with the US and other nations, this type of communication became ineffective in 2023,” she contends.

“Ultimately, his diplomatic strategy did not adapt rapidly enough.”

On September 27, 2024, a significant shift occurred for Ukraine in New York. The catalyst was not advancing Russian forces, but the political resurgence of the US, Ukraine’s key ally.

That day, shortly before the US Presidential election, Zelensky held a last-minute meeting with Trump in Trump Tower.

Tensions between them had escalated prior to this meeting, with Zelensky stating days earlier that Trump “doesn’t truly understand how to resolve the conflict,” after Trump claimed he could end it “in a single day.”

Following their Trump Tower meeting, both men appeared uncomfortable.

Despite announcing a “shared perspective” on ending the war, their nonverbal cues suggested a lack of rapport.

They would not meet again until five months later in the Oval Office, in what became a diplomatically challenging encounter for Kyiv.

“Trump should have been drawn to him,” remarked Vadym Prystaiko, who was present at their initial meeting after Zelensky’s 2019 election victory. “Zelensky perceived Trump as somewhat similar to himself, a media figure who transitioned into politics and held anti-establishment views,” he noted.

Prystaiko, formerly Ukraine’s ambassador to the UK, was dismissed in 2023. Although Kyiv offered no official explanation, it followed Prystaiko’s criticism of Zelensky’s response to a controversy regarding gratitude for British military aid. He perceived “a degree of sarcasm” in his president’s reaction, deeming it “unhealthy.”

“Zelensky has never operated as a traditional diplomat,” Prystaiko added. “He does not fit the mold of a conventional political leader engaging in typical political pleasantries.”

“The relationship with Trump is characterized by volatility,” observed Volodymyr Fesenko, director at the Penta Center for Political Studies. “Periods of constructive collaboration are interspersed with sudden crises.”

Adding to this dynamic are their verbal exchanges. Trump has faulted Zelensky for initiating the conflict, labeling him a “dictator,” while Zelensky accused his US counterpart of “inhabiting a Russian disinformation sphere.”

While Fesenko believes Zelensky is continuously adapting his strategies to cultivate a functional relationship with Washington, Zolkina suggests the underlying issues are more profound.

“A power dynamic exists between the US administration, the Kremlin, and Kyiv,” she asserts. “Ukraine is perceived as the weaker entity in this equation. For Trump, Zelensky does not operate on the same level, and that constitutes a core problem.”

The ensuing Oval Office meeting with Trump and Vice President JD Vance marked a turning point. It was the first instance where Zelensky appeared to be politically outmaneuvered, facing accusations of “insufficient gratitude” and “reckless rhetoric regarding World War Three.”

His defensive body language, such as crossed arms, was also noticeably new.

Zelensky typically projects ease when hosting or visiting global leaders, comfortable on stage and adept at using timely humor—but this encounter differed significantly.

A proposed mineral agreement, where Zelensky initially suggested leveraging Ukrainian mineral resources for sustained military assistance, remained unsigned and evolved into a less advantageous proposition for Kyiv.

The US also briefly suspended military aid and intelligence sharing, signaling a need for greater alignment with its objectives.

However, some official perspectives downplay the Oval Office meeting as a calamity.

“No one interpreted it as a conclusive breakdown,” claims Ihor Brusylo, the deputy head of the Presidential Office who accompanied Zelensky to the White House. “We deliberated on future steps. It was not a disaster.”

When US National Security Advisor Mike Waltz concluded the meeting, “we simply shrugged and decided to return to the hotel,” he recounted.

“My sense is that on a personal level, they [Trump and Zelensky] have a positive rapport,” he adds. “They possess a mutual understanding, characterized by frankness and honesty.”

Regardless of the private dynamic, signs of adaptation from Zelensky have emerged post-meeting. European allies reportedly encouraged him to adopt a more conciliatory stance, acknowledging the ongoing need for US support to counter Russian aggression.

Yet, some argue for further concessions.

“Conflict transforms all involved, and we have all been altered in some respect. However, I believe Zelensky’s core character remains consistent—for better or worse,” stated Olga Onuch, professor of Comparative and Ukrainian Politics at the University of Manchester.

“It is evident that certain actors find negotiating with Zelensky challenging. This is due to his firm adherence to established red lines.”

Brusylo concurred, “Persuading Zelensky to yield is exceptionally difficult. It resembles compressing a spring – increased pressure results in greater resistance.”

Paradoxically, external challenges, whether political or diplomatic, tend to foster internal unity in Ukraine. The Oval Office encounter was no exception, as Zelensky’s approval ratings surged to approximately 70%.

“Zelensky wields considerable power, derived from his persona and a close circle of advisors,” Zolkina argues.

Orysia Lutsevych, head of the Ukraine Forum at Chatham House, noted the striking surge in Ukrainian support for Zelensky post-Oval Office, interpreting it almost as a national affront.

“People are rallying around him, what he symbolizes, and his conduct.”

Prystaiko contends that attempts by the Americans to undermine him might backfire, as “he could easily secure re-election.”

However, some political analysts, like Zolkina, express skepticism. “I doubt he recognizes that this surge in popularity is a direct response to Trump’s actions, rather than an affirmation of his personal standing,” she suggests.

“He harbors substantial political ambitions for a second term and exhibits a degree of egocentricity common among leaders at his level.”

Professor Onuch offers a different perspective, suggesting that Zelensky’s motivations extend beyond political power. “[He is] a more astute, thoughtful, and tactical political player than he is often credited for.”

Nonetheless, envisioning a second Zelensky term presents challenges, primarily due to the demanding nature of the role, even in a post-war scenario.

Currently, Arnold speculates that an exhausted Zelensky might prefer not to seek re-election, potentially seeking an exit from frontline politics.

Looking ahead, Zelensky must avoid another Oval Office misstep. Given Trump’s affinity for deal-making, will Ukraine’s leader consider engaging him in a round of golf?

“He adapts quickly,” Brusylo concludes. “If golf becomes a necessity, I am confident he will master it.”