


Last month’s Oval Office meeting between Ukrainian President Volodymyr Zelenskyy, President Donald Trump and Vice President JD Vance was a turning point in the conflict between Ukraine and Russia.
Just days after the fiery exchange in which Zelenskyy traded barbs with the U.S. leaders, Trump announced the temporary suspension of all military aid to Ukraine. The move unsettled European leaders, prompting a flurry of diplomatic activity as they sought to reaffirm their commitment to Kyiv while assessing the broader implications of the shift in U.S. policy.
While he was obstinate in the Oval Office meeting, in the days that followed, Zelenskyy worked to repair relations — privately apologizing to Trump, publicly expressing gratitude for U.S. support and endorsing Trump’s proposal for a ceasefire. With tensions easing, the administration ultimately resumed arms deliveries.
The whole saga, with Zelenskyy risking U.S. support through his quarrel with Trump before ultimately backing down, demonstrates how unprepared the Ukrainian leader was to engage with the new administration.
Trump hit the nail on the head when he glibly observed in real time that the meeting would make for good TV. The contrast between America’s and Ukraine’s leaders was on full display during the discussion.
The president and vice president were professionally attired in suits and ties befitting the stateliness of the Oval Office while Zelenskyy opted for a casual outfit resembling a tracksuit.
During the height of his country’s conflict with Russia, Zelenskyy forewent suits and ties for green military fatigues to send the message that his was a nation at battle.
Years into the conflict, however, this sartorial choice backfired, and Zelenskyy looked like a petulant teen seated among adults.
When conducting business and negotiating, it is vital to understand the variables at play to drive toward the best possible achievable outcome.
The Trump administration’s approach toward the war has taken a sharp turn away from policies enacted by the Biden administration, but rather than adjust his tactics and secure the best possible outcome for Ukraine, Zelenskyy opted to be argumentative and petulant in how he spoke to Vance and Trump.
Their united front left him completely outmaneuvered. Views may differ on the wisdom of engaging directly with Russian President Vladimir Putin to broker a ceasefire, but Zelenskyy’s behavior was unbecoming, rude and insulting to both the men he was meeting with, as well as the office of the presidency.
Trump correctly asserted that the reason Ukraine has survived is a result of massive American military, financial and political support. Vance chided Zelenskyy, pointing out that he had not expressed gratitude for all that America has done but instead was arguing that the Trump administration’s approach was the wrong one.
Anyone who has observed Trump knows he is a tough negotiator who makes up his own mind and is not likely to respond well to being lectured. Did Zelenskyy think directly confronting and arguing with the president before a live audience would lead Trump to suddenly change his mind?
One of the key aspects of smart communicators is that they listen more than they speak and read the room, and that is precisely what Zelenskyy failed to do.
It was astonishing to consider that the same man who was masterful in the early days of the conflict at using international media to advance his case faltered so badly in terms of his judgment and communication while sitting in the Oval Office with the most powerful leaders in the world as cameras rolled.
Trump told him multiple times that he did not “have the cards,” which was a direct warning to Zelenskyy that he lacked strength and should not be trying to pressure the United States to abandon its current trajectory, however much Ukraine might disagree with it.
The body language of the encounter also told the story. To his credit, the often-volatile Trump was reserved and dignified. He didn’t express much emotion, nor could you see agitation in the way he carried himself. For someone who has joked about how boring it is to be “presidential” that was precisely how he appeared.
Zelenskyy, on the other hand, was a coiled ball of kinetic frustration who looked like he might leap out of his seat at any time and bolt from the room.
A photo of Ukraine’s ambassador to the United States went viral shortly after the meeting, showing her sitting and observing the proceedings with her head in hand. She understood the disastrous consequences that came as a direct result of this catastrophic sit-down.
Whether Zelenskyy likes it or not, the political winds have shifted. But rather than alter course and adjust the sails to steer toward the best possible outcome for his constituency, he chose to resist the new direction. It was a fool’s errand, and his behavior itself was foolish.
Zelenskyy’s approach in the Oval Office hurt his cause, casting doubt on his ability to negotiate a resolution aligned with U.S. interests. While he has since worked to mend relations, Zelenskyy faces a growing challenge: proving he can deliver a path forward that satisfies both Ukraine’s survival and America’s strategic priorities.
This meeting will be remembered as a turning point in which America decided that the best shot at resolving the Russia-Ukraine war was to impose a solution rather than work with Zelenskyy to arrive at one preferable to him.
You may not like the cards you’re dealt, but as a leader your job is to best represent your nation’s interests and secure the best possible outcome. In the Oval Office, Zelenskyy failed the test, and the winds of change will sweep him toward whatever agreement the world’s only true superpower ultimately decides.
Evan Nierman (evan@redbanyan.com) is founder and CEO of global strategic communications firm Red Banyan.