WASHINGTON--When U.S. 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 criticize Putin. The Russian president, shunned by multiple presidents, praised Trump for working to improve Russian-U.S. 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 U.S. 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 Zelenskiy 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. Zelenskiy says he would like to see a ceasefire first followed by security guarantees.
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 Zelenskiy 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.
