Trump cranks up pressure on Zelensky ahead of his high-stakes White House return

Damond Isiaka
15 Min Read

President Donald Trump is ratcheting up pressure on Ukraine to agree to terms to end the war with Russia, echoing some of Moscow’s talking points two days after meeting President Vladimir Putin.

Trump will host a summit Monday with Ukrainian President Volodymyr Zelensky and a bodyguard of European leaders in the most important moment yet in a quickening push to end the brutal conflict that followed Russia’s 2022 invasion.

The White House meeting is also one of the most critical days for European security and the Western alliance since the end of the Cold War, and it will test Trump’s sincerity and his capacity to lead Ukraine and Russia toward an exit ramp likely to satisfy neither side.

It follows Trump’s summit with Putin on Friday in Alaska, widely viewed outside the administration and MAGA world with dismay as the US president welcomed his guest, who is accused of war crimes, with applause. Trump offered several major symbolic and process concessions to Putin for few public undertakings in return.

But Trump’s envoy Steve Witkoff insisted Sunday on CNN that Russia had softened its opposition to post-war Western security arrangements for Ukraine and was ready to make significant land swaps in any deal to end the fighting.

“We agreed to robust security guarantees that I would describe as game-changing,” Witkoff told Jake Tapper on “State of the Union.”

Differing perceptions of the Trump summit will influence Monday’s White House talks.

European officials told CNN privately that Putin called for Ukraine to hand over swaths of the critical strategic and economic powerhouse region of Donbas, which his troops have failed to seize in three and a half years of fighting. This would be all but impossible for Zelensky to accept — politically, constitutionally, economically and strategically. His forces have suffered severe losses defending farmland and cities seen as a bulwark against future Russian aggression.

No one outside the US and Russian delegations knows for sure what happened in Alaska. And the president’s invite to European leaders and his energetic push for peace should not be prejudged before vital meetings take place.

Trump insisted on social media Sunday that “great progress” was being made.

But hanging over Monday’s White House meetings is his warning to Ukraine after the summit with Putin.

“Make a deal,” Trump said on Fox News. “Russia is a very big power, and they’re not.”

The president exerted more pressure on the Ukrainian leader on Sunday night in a post on Truth Social that also echoed Russia’s stance that Zelensky’s country can never join NATO. “President Zelensky of Ukraine can end the war with Russia almost immediately, if he wants to, or he can continue to fight,” Trump wrote.

Russian President Vladimir Putin and US President Donald Trump hold a press conference after their meeting at Joint Base Elmendorf-Richardson in Anchorage, Alaska, on Friday.

This prompted concern in Kyiv and other European capitals that Trump will try to impose Putin’s ideal vision of a settlement on Zelensky and that if the Ukrainian leader refuses this impossible choice, Trump will blame Kyiv and walk away from the conflict entirely.

This points to a vital dynamic in Monday’s White House meeting, which could turn into an extraordinary, televised spectacle if the president opens large portions of it to the cameras — a possibility for which his visitors must prepare.

Is Trump prepared to act as a broker who will bring Ukraine and its European supporters and Russia to a point where they can accept painful concessions despite their bitter antipathy? Or does Trump’s acceptance of Putin’s opposition to an immediate ceasefire and postponement of tough new US sanctions on Moscow mean the US will now side with Russia against Ukraine and Europe?

“Trump has done something useful in his drive to end the war: Negotiations have shown the world that Putin — not the Ukrainians or Europeans — is the one who’s unwilling to stop fighting without conditions like handing over more land than he has already illegally conquered,” said Josh Rudolph, managing director and senior fellow of strategic democracy initiatives at the German Marshall Fund.

“The question is now which side America is on.”

Trump is a vital player despite mistrust of his motives

Despite criticism of the Alaska summit and Trump’s empathy toward Putin, the US president remains the potential catalyst to any peace deal. While there’s little sign the Russian leader wants peace, US pressure, properly applied, might be the one thing that could stop him fighting.

And while Europe will play a major role in Ukraine’s security after any deal, it lacks influence with Putin and can’t fulfill a promised peace enforcement mission without Trump’s support.

In this context, speculation in the Washington bubble over whether Trump is trying to rush the Ukraine war to a conclusion to secure a Nobel Peace Prize is pointless. If he could somehow end the conflict fairly, who cares about his motives?

Bad Oval Office memories

If Europe is secured, Trump might even fulfill his craving for the prize that his first presidential predecessor, Barack Obama, won. However, US support for Israel as it comes closer to fully occupying Gaza amid starvation conditions might still disqualify him from the Nobel Committee’s consideration.

Zelensky’s arrival will stir memories of his disastrous last Oval Office visit in February.

Shocking live footage of Trump and Vice President JD Vance berating the Ukrainian leader means his escort this time from the leaders of France, Germany, Britain, Italy, Finland, NATO and the European Commission is seen as a protection squad.

But Europe has far more at stake than Zelensky’s reputation.

The possibility that Russia could triumph in Ukraine and win vindication for its illegal invasion is the biggest geopolitical threat to Europe since the fall of the Soviet Union.

“This is existential also for European security. So, minimizing the role of Europe here, be it the United Kingdom, be it Poland, be it Finland, be it France, be it Germany, is not the way to go,” Fiona Hill, who served as a Russia expert in Trump’s first term, said Sunday on CBS’ “Face the Nation.”

US President Donald Trump and Vice President JD Vance meet with Ukrainian President Volodymyr Zelensky at the White House in Washington, DC, on February 28.

“Europe has to have an equal say in all of this,” Hill said. “This is about Europe’s future and the future of European security, not just about Ukraine’s.”

But it will be hard to create momentum for genuine peacemaking even as the administration pushes for a three-way summit among Trump, Putin and Zelensky, possibly as soon as the end of this week.

“The challenge is to try to achieve alignment between what look like very disparate things — what Trump wants, what the Europeans want, what Putin wants,” said Nicholas Dungan, a senior member of the European Leadership Network. “The Europeans want a sovereign Ukraine. Trump wants a peace deal. These are not the same thing,” said Dungan, who is also CEO of CogitoPraxis, a strategic advisory firm.

What Putin wants may be impossible for Ukraine and its European allies to accept.

The Russian leader dictated terms alongside Trump in Alaska, demanding attention to the “root causes” of the war. This is his shorthand for various factors including the ousting of Zelensky, huge cuts to Ukrainian armed forces that would compromise Kyiv’s capacity to repel any future invasion, and a redeployment of NATO forces from Moscow’s former Soviet-era orbit in Eastern Europe.

The disconnect helps explain why Marco Rubio, the secretary of state and Trump’s national security adviser, is more downbeat than the US president or Witkoff.

“We made progress in the sense that we identified potential areas of agreement, but there remains some big areas of disagreement,” Rubio said on ABC. “We’re still a long ways off. I mean, we’re not at the precipice of a peace agreement; we’re not at the edge of one.”

Trump’s mood will be critical

European leaders traveling to the White House include French President Emmanuel Macron, German Chancellor Friedrich Merz, Italian Prime Minister Giorgia Meloni, British Prime Minister Keir Starmer, Finnish President Alexander Stubb, NATO Secretary General Mark Rutte and European Council President Ursula von der Leyen.

Trump has good personal relationships with several of them, especially Meloni; Stubb, a golf partner; and Starmer. Rutte is seen as something of a Trump whisperer.

But the president’s mood will be crucial, especially after critical media coverage of his lavish welcome for Putin.

Europe’s influence is also in question. Trump had adopted the European position that a ceasefire was a vital first step in peacemaking and said he’d be disappointed if he didn’t secure one in Alaska. But after meeting with Putin, he backed Russia’s stance that a push for a full peace deal is best. This was a win for Russia, since a full settlement could take months to negotiate and give more time for its forces to seize more land while continuing attacks against civilians.

Top row from left: Germany Chancellor Friedrich Merz, British Prime Minister Keir Starmer, French President Emmanuel Macron and Italian Prime Minister Giorgia Meloni. Bottom row from left: European Commission President Ursula von der Leyen, Finnish President Alexander Stubb and NATO Secretary General Mark Rutte.

Europe is far more skeptical than the White House about the sincerity of any undertakings Putin offered to Trump on Friday.

Macron wrote on X on Saturday that it will be “essential to draw all the lessons from the past 30 years, in particular from Russia’s well-established tendency not to honor its own commitments.”

But Witkoff said Trump’s acceptance of Putin’s ceasefire sequencing was a good sign.

“We made so much progress at this meeting with regard to all the other ingredients necessary for a peace deal that we, that President Trump, pivoted to that place,” Witkoff told CNN’s Tapper.

The Russian president tried to split the allies while in Alaska. “We expect that Kyiv and European capitals will perceive (the talks) constructively and that they won’t throw a wrench in the works; they will not make any attempts to use some backroom dealings to conduct provocations to torpedo the nascent progress,” Putin said.

Witkoff pushed back at criticism of Trump by insisting that Putin had accepted a security guarantee among Ukraine, European powers and the US similar to NATO’s Article 5 clause that an attack on one is an attack on all. This undertaking would not, however, be linked to NATO in any way.

He also told CNN that Putin had offered “concessions on several of the regions,” but refused to say what they were. And there has been no confirmation from the Kremlin.

But in return for an Anchorage welcome that purged his international pariah status, Putin offered political gifts to Trump. These included an echo of the president’s false claims that mail-in voting is undemocratic and backing for Trump’s claim the Russians would not have invaded Ukraine had he been in office.

US bullishness about an Article 5-style guarantee is also a little strange, since Putin would demand extraordinary steps in return. And there are already concerns that Trump wouldn’t honor NATO’s mutual defense clause if Russia attacked one of the alliance members close to its borders, perhaps in the Baltic states. The idea he’d would risk war with Russia to save Ukraine seems absurd.

This might also put Trump at odds with his political base, which shares his doubts about America’s protection of European allies and his desire to avoid more foreign wars.

Conservative media has been running interference for Trump all weekend, with several key MAGA-friendly sites already portraying Zelensky as an obstacle to peace and the impediment to yet another Trump “win.”

But the imagery of Trump as a peacemaker is a powerful one among his most loyal supporters.

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