Donald Trump has long highlighted his “good chemistry” with Russian President Vladimir Putin. Yet, in the lead-up to their first face-to-face meeting in six years, the U.S. president has been quietly pressing European counterparts and White House aides with a pointed question: has Putin really changed?
Three people familiar with the matter told CNN that this curiosity reflects Trump’s growing irritation with Moscow ahead of Friday’s talks in Alaska, where the two leaders are set to discuss ending Russia’s prolonged war in Ukraine. Trump had pledged, even before returning to the Oval Office, to bring the conflict to a swift close. Instead, Putin has escalated military operations this year, rejecting multiple ceasefire initiatives.
Inside the administration, some analysts see faint signs of flexibility in the Kremlin’s short-term objectives, sparking cautious optimism. However, U.S. intelligence assessments remain firm: Putin’s core territorial ambitions are intact. Sources briefed on recent intelligence say he would likely use a ceasefire to rebuild his military and could mount another push toward Kyiv. He is also still opposed to Ukraine joining NATO or hosting foreign peacekeeping forces.
“From Putin’s perspective, he’s already ahead — so why compromise?” said one person aware of the assessments. “He can hold on to what he’s taken, then aim for more later.”
Concerns From Europe and Kyiv
Trump’s pursuit of insight into Putin comes as Ukrainian and European officials fear that the Kremlin could be steering the White House into granting Moscow a symbolic win — hosting Putin on U.S. soil without Ukrainian President Volodymyr Zelensky at the table. One European official dismissed Moscow’s latest overture: “They want the war to end only on their terms, which are the same extreme demands they’ve always had. That’s not peace, it’s capitulation.”
Some European diplomats, however, believe Trump might be able to broker a deal, noting his evolving approach to the conflict. On Wednesday, Trump warned that Russia would face “very severe consequences” if Putin proved unwilling to negotiate — without detailing what those might be.
### The Putin Puzzle
Understanding Putin’s intentions has long been one of the toughest tasks in global intelligence. A former KGB officer, the Russian leader keeps decision-making within an extremely tight circle, making it hard to know whose advice shapes his actions. While decades of surveillance have given Washington a deep profile of Putin, his daily calculations remain opaque.
The U.S. did correctly predict the 2022 invasion of Ukraine, but Trump has often questioned intelligence reports, especially those involving Russia. Officials say analysts believe Putin still sees prolonging the war as serving his interests.
Trump remains convinced that his personal read of Putin could unlock a breakthrough, telling reporters Tuesday he’ll know “within the first two minutes” of meeting whether a deal is possible.
### A Shift in Trump’s Tone
European officials note that while Trump wonders if Putin has changed, it may be Trump himself who has shifted. “Earlier this year, he underestimated Putin,” one U.S. official said. “Now he recognises him as a ruthless operator.”
Frustration toward Moscow, insiders say, spiked earlier this summer. Steve Witkoff, Trump’s main channel to Russia, privately complained that the Kremlin was dragging out talks. Trump, too, began using harsher language when discussing Putin, according to those present in meetings.
Some intelligence suggests Putin could be willing to settle for consolidating current territorial gains and securing new economic deals — but analysts doubt he would offer such terms at the outset. In the final days of the Biden administration, U.S. intelligence had warned Trump advisers that Putin’s priority remained controlling Ukraine and that he would exploit any rush toward negotiation.
### Pandemic Isolation and Paranoia
Putin’s worldview may have hardened during the pandemic, when he isolated at his residence outside Moscow, drastically limiting personal contact. Those years, analysts say, reduced the influence of moderates in his circle and increased reliance on hardliners. While less cut off today, Putin remains difficult to read. Ukrainian intelligence has even alleged the use of body doubles — claims widely disputed abroad.
### A Determined Adversary
After nearly four years of fighting, experts say Putin’s resolve to subjugate Ukraine has deepened. “He now sees victory as essential to his survival in power,” said Angela Stent, a former senior U.S. intelligence officer.
That stance fuels concerns in Europe that Trump could be tempted into a deal that rewards Moscow’s aggression. Zelensky warned this week that Putin is “definitely not preparing” to end the war and will try to portray the summit as his personal triumph.
Reports that Witkoff discussed allowing Russia to retain occupied Ukrainian territory in exchange for a ceasefire have unsettled some allies. While Trump told European partners that territorial decisions rest with Zelensky, analysts caution that focusing only on land swaps ignores Putin’s larger ideological mission.
“Putin isn’t just transactional anymore — he’s driven by imperial ambitions,” said former U.S. Ambassador Michael McFaul. “That makes him far harder to negotiate with.”
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