Putin Is Sure to Test Trump’s Ukraine Turnabout

By Noah Rothman

Wednesday, September 24, 2025

 

The president seems to have had another change of heart. And this time, it’s a big one.

 

“I think Ukraine, with the support of the European Union, is in a position to fight and WIN all of Ukraine back in its original form,” Trump wrote in a social media post on Tuesday. The president said that Russia has fought “aimlessly” for over three years, making the Kremlin out to be a “paper tiger.” Ukraine, meanwhile, has “Great Spirit,” is “only getting better,” and could potentially reconstitute its pre-2014 borders — “maybe even go further than that!”

 

Trump’s social media statement coincides with the annual gathering of world leaders at the United Nations in New York City. There, the president demonstrated that his about-face was no errant thought.

 

Trump expressed regret for convincing himself that he had some personal pull with Russian President Vladimir Putin. That relationship “didn’t mean anything unfortunately,” he said. Trump criticized European states, including Hungary’s Viktor Orbán, a MAGA favorite, for purchasing Russian oil. “It’s embarrassing to them,” he remarked during his address to the U.N. General Assembly. On the sidelines, Trump said the Russian economy is “crashing,” and Ukraine’s continued resistance has ensured that Russia “doesn’t look very distinguished.” Seated alongside Ukrainian President Volodymyr Zelensky, Trump was asked if he supports NATO efforts to “shoot down” Russian aircraft if they penetrate the alliance’s airspace. “Yes, I do,” Trump replied. Zelensky, clearly taken aback, smiled after a beat. He has done a lot of smiling this week. And Trump smiled right back.

 

The president has performed turnabouts like these in the past, but those pivots were not accompanied by dramatic shifts in U.S. posture. In fact, it often seems like the Pentagon is running on autopilot, preprogrammed to execute American retrenchment away from its overseas allies — the policy that Trump retailed on the campaign trail — regardless of the president’s current posture. Trump may not take much interest in seeing the policy he articulated made manifest by his subordinates. His subordinates may have a much stronger interest in not listening to the president. We shouldn’t judge how Trump’s words will be received in Washington.

 

But we can guess how they have been received in Moscow.

 

“The idea that Ukraine can recapture something is, from our point of view, mistaken,” Kremlin spokesman Dmitry Peskov told a local radio station. He bitterly mourned how this summer’s Anchorage summit produced “close to zero” results, and he fretted that Trump’s sudden hostility to Moscow’s position will ensure that the war continues. “We are doing this for both the present and the future of our country,” Peskov said. “Therefore, we have no alternative.”

 

Putin and his representatives didn’t come to Alaska to secure a durable cease-fire. They arrived with the impression that Trump would come bearing concessions, providing Russia with advantages it could not secure on the battlefield and setting Moscow up for a more advantageous fight for even more Ukrainian territory down the road.

 

The summit collapsed, and the war that Russia had no intention of halting grinds on, but Ukraine is no longer steadily losing territory as it was earlier this year — albeit meters at a time, and at significant cost to Russia’s aggressor forces. It is counterattacking. And Trump’s intelligence about the economic conditions inside Russia is accurate. Fuel shortages exacerbated by Ukrainian attacks on Russian petroleum refineries and infrastructure have become a visible crisis. And Moscow’s recent tax hikes, which will dampen overall growth, suggest the regime is more concerned about its ballooning budget deficit than it lets on.

 

That is perhaps why Russia is, as so many warned over the years, not content to limit its military provocations to Ukraine’s front lines.

 

In early September, Russia sent 19 one-way attack drones deep into Polish territory, forcing airport closures as far away from the Ukrainian border as Warsaw. The incursion compelled NATO forces to engage and shoot down Russian military assets over the alliance’s soil — a reckless provocation that most now believe was a deliberate effort to test the alliance’s military and diplomatic response to a Russian incursion.

 

In an even more provocative and deliberate exercise on September 19, three Russian MiG-31 fighter jets entered Estonian airspace and lingered there, just off the coast over the Gulf of Finland, for 12 minutes. Estonian sources claim that the Russian pilots acknowledged the efforts by the two Italian F-35 pilots who intercepted the Russian jets to usher them out of NATO airspace, but the Russian pilots disregarded their orders for several tense minutes before consenting to be escorted away.

 

Poland and Estonia both have since invoked NATO’s Article 4 — a requisite prelude to but not necessarily a trigger for the Alliance’s Article 5 mutual defense provisions. This is probably what Moscow has expected to see: NATO anti-air defense systems and fighter jets scrambling to meet its forces combined with an energetic flurry of diplomatic activity reaffirming the alliance’s cohesion. But we now have two provocations in the same month. Trump’s tough talk with the Kremlin may beget a third.

 

In that social media post in which Trump mused about Ukraine’s reconquest of all its occupied lands, skeptics of the Ukrainian cause have zoomed in on his invocation of “the support of the European Union” and speculated that it was an indication that Trump still wants to halt U.S. involvement in the conflict. The EU is now an intermediary through which the U.S. transits lethal arms to Ukrainian forces (although the Pentagon has done its best to slow-walk that), as well as a supporter of Kyiv on its own terms.

 

That is likely what Trump was talking about. But if there’s any ambiguity there, the Kremlin will seek clarity. Putin will test the proposition put to him by Trump — that the U.S. will now crack down on Russian oil purchasers, support Ukrainian offensives aimed at recapturing territory long in Moscow’s control, and back NATO forces engaging with Russian “aircraft,” not unmanned drones, if they enter the alliance’s airspace.

 

Trump’s tough talk is a challenge to the Kremlin, and Moscow may feel strategically compelled to meet it. Putin will see just how steely Trump’s resolve really is. And if he finds mush, he’ll push. Let’s hope the president meant it this time.