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Published : 15 Aug 2025, 10:33 AM
When US President Donald Trump and Russian President Vladimir Putin met in Helsinki in 2018, the pair alarmed allies with a friendly encounter where Trump sided with the Russian leader over his own intelligence agencies on election interference.
Trump flies to a meeting in Alaska with Putin on Friday in a different public mood - impatient with the Russian's unwillingness to negotiate an end to his war in Ukraine and angry over missile strikes on Ukrainian cities.
The world is waiting to see if it will be this tougher version of Trump who shows up in Anchorage or if it will be the former real estate tycoon who has sought to ingratiate himself with the wily former KGB agent in the past.
The answer could have deep implications for European leaders concerned that Russia, if allowed to absorb parts of Ukraine, will be more aggressive toward NATO allies near Russia like Poland, Estonia, Lithuania and Latvia.
It matters even more for Ukraine, which has been losing ground to Russian forces after three-and-a-half years of grinding combat.
Despite his harsher tone toward Putin over the past months, Trump has a more extensive history of trying to placate the Russian leader. When Russia invaded Ukraine in 2022, Trump declined to directly criticise Putin. The Russian president, shunned by multiple presidents, praised Trump for working to improve Russian-US relations.
Kremlin watchers are looking to see whether Trump will be enchanted by Putin again and swayed by his argument that Russia has a right to dominate Ukraine.
"It's a reasonable concern to think that Trump will be bamboozled by Putin and cut a terrible deal at Ukraine’s expense," said Dan Fried, a diplomat for several US presidents who is now at the Atlantic Council.
But a different outcome is also possible, added Fried. "There’s a reasonable prospect that the administration will wake up to the fact that Putin is still playing them."
The Trump administration has sought to temper expectations, with White House press secretary Karoline Leavitt telling reporters on Tuesday the meeting would be a "listening exercise."
Trump told reporters on Wednesday that he might broker a second meeting that includes both Putin and Ukraine President Volodymyr Zelensky if the Alaska session goes well.
Russia has given no indication it is prepared to make concessions amid Ukrainian worries that Trump might make a deal without their input. Zelensky says he would like to see a ceasefire first followed by security guarantees.
SWEETENERS AND COMPLAINTS
When Trump assumed office again in January, the Republican president tried to revive the warmth between the two leaders from his first term, expressing sympathy for Putin's isolated position in the world and vowing to end the war in Ukraine in 24 hours.
As the administration eased pressure on Russia, some Trump aides parroted Russian talking points to the dismay of Ukraine's backers. In March, U.S. special envoy Steve Witkoff implied in a podcast interview with conservative commentator Tucker Carlson that Russia had a right to capture four mainland regions of Ukraine – Donetsk, Luhansk, Zaporizhzhia and Kherson - because "they're Russian speaking."
And in a dramatic White House meeting in February, Trump and Vice President JD Vance berated Zelensky for his handling of the war, to the delight of hardliners in Russia.
Despite all the sweeteners, the Russian leader has refused to play along with Trump's efforts to steer the two sides into a peace deal. Putin has talked to Trump regularly but has kept up deadly bombing raids against Ukraine.
The ongoing bloodshed prompted Trump to shift to a tougher stance in July and complain that Putin was stalling him. Trump has agreed to send new weapons to Ukraine - that Europe will pay for - and has threatened new financial penalties for Moscow.
Trump last week imposed an additional 25% tariff on India for buying Russian oil - indirect pressure on Moscow - but has held back from following through on his threats to impose stiffer sanctions. On Wednesday, he threatened "severe consequences" if Russia will not make a deal.
"While the tone coming out of the White House has shifted, it has not yet been followed up with an expansion of US sanctions — Trump's deadlines for additional sanctions keep getting pushed back — or new financial commitments from Washington to strengthen Ukrainian security," said Nicholas Fenton, of the Europe, Russia, and Eurasia Program at the Center for Strategic and International Studies.
On Monday, Trump said he should know within two minutes whether Putin is willing to make concessions. "I may say, lots of luck. Keep fighting. Or I may say, we can make a deal," he said.
THE LURE OF THE DEAL
For Trump, who is drawn to the spectacle of a high-profile summit with the world watching, the lure of making a deal is strong.
He has engaged in an open campaign for a Nobel Peace Prize this year, pointing to what he has claimed as his diplomatic victories, and has unnerved US allies with his eagerness for a Ukraine peace deal that they fret could embolden Putin.
In recent days, Ukrainian and European leaders have protested Trump's assertion that Russia and Ukraine will have to engage in land swaps in order to reach a peace deal.
While Russia occupies Crimea and large swaths of eastern Ukraine, the Ukrainians no longer hold any Russian territory, raising the question of what, exactly, could be exchanged.
Trump insists that, given his personal relationship with Putin, he is the only one who can bring the war to an end.
John Bolton, who was one of Trump's national security advisers in his first term and is now a sharp critic, said he was concerned that Putin was "beginning to work his magic" on Trump.
"Personal relations obviously have a place in foreign affairs, just like they do in everything else. But when you're one of the world's hard men like Vladimir Putin, this is not a matter of emotion, this is a matter of cold calculation. Trump doesn't get that point," Bolton said.
In a social media post on Wednesday, Trump complained that "very unfair media is at work on my meeting with Putin," citing the use of quotes from "fired losers" like Bolton.
