For weeks, President Donald Trump and his allies have insisted he’s no longer charmed by Vladimir Putin. They claim his sudden shift from years of effusive praise to open criticism of the Russian leader stems from Putin’s own behavior, not Trump’s misjudgment.
But as Trump prepares for his most high-profile meeting with Putin yet — on U.S. soil in Alaska — his recent rhetoric has many wondering whether he’s setting himself up for another embarrassing misread of the Kremlin.
From “Listening Exercise” to Lofty Promises
The Alaska summit, announced just a week ago, was initially framed as low stakes. White House Press Secretary Karoline Leavitt downplayed expectations, calling it a “listening exercise.” Secretary of State Marco Rubio echoed the sentiment, while Trump himself hinted that a second meeting — possibly involving Ukrainian President Volodymyr Zelensky — would need to be earned.
By Thursday, however, Trump had shifted tone entirely. Speaking to Fox News host Brian Kilmeade, he said:
“I believe now he’s convinced that he’s going to make a deal. He’s going to make a deal. I think he’s going to.”
Hours later, in the Oval Office, he doubled down:
“I think President Putin will make peace.”
This is far from the first time Trump has vouched for Putin’s intentions. In February, he declared:
“I know him very well… I trust him on this subject.”
Six months of continued Russian aggression have since rendered those assurances hollow — yet Trump appears willing to make them again.
A Pattern of Misjudgment
Trump has admitted in recent weeks that he thought a Ukraine peace deal would be “the easiest one” to achieve. He’s also acknowledged that Putin’s flattering words didn’t translate into real concessions, at one point dismissing them as “bullshit.”
One particularly revealing anecdote came last month, when Trump recounted telling First Lady Melania about a “wonderful” conversation with Putin — only for her to immediately inform him that Putin had just bombed another Ukrainian city.
Critics say these episodes expose Trump’s susceptibility to flattery and his tendency to conflate personal rapport with geopolitical reality.
Searching for a Narrative
Behind the scenes, some aides are reportedly trying to give Trump an “out” — suggesting Putin has changed, so Trump can claim he wasn’t wrong to initially see him as a “good guy.” CNN quoted one source as saying:
“Many around Trump are now trying to give him the idea that Putin changed so he has a reason to say that he wasn’t wrong.”
The risk, analysts warn, is that Trump may actually believe it.
Americans Aren’t Buying It
Polling suggests the public remains skeptical of Trump’s instincts. A Pew Research Center survey released Thursday found 59% of Americans have little or no confidence in Trump to make wise decisions about the war in Ukraine. Only 16% are “very confident.”
When asked whose side Trump favors, about half said he sides too much with Russia — a perception that has dogged him since his first meeting with Putin in Helsinki in 2018, where he famously sided with the Russian leader over U.S. intelligence agencies.
High Stakes in Alaska
Friday’s summit offers Trump a chance to prove his critics wrong — to show he can extract meaningful concessions from Putin rather than simply validate Moscow’s position.
But history suggests caution. Trump’s past willingness to take Putin at his word, combined with his eagerness to claim a foreign policy win, has repeatedly left him vulnerable to manipulation.
If Alaska becomes another stage for empty promises and flattering photo ops, it may cement the narrative that Trump has once again been outplayed by one of America’s most formidable adversaries.