President Trump sat down with Ukrainian President Volodymyr Zelensky at the NATO summit on Wednesday and marveled at how far the two leaders had come, from a February 2025 Oval Office meeting that ended with Zelensky being escorted out before lunch to a warm bilateral exchange capped by a major defense pledge.
"We've actually developed a good relationship! Hard to believe, right? From the Oval Office to now," Trump told reporters, with Zelensky seated beside him, the New York Post reported.
The shift matters because it came with substance attached. Trump pledged to discuss granting Ukraine a license to manufacture its own Patriot interceptor missiles, a move his predecessor, Joe Biden, refused to make and one that would represent one of the biggest changes in U.S. military support for Ukraine since Russia's full-scale invasion in 2022.
The contrast with early 2025 is hard to overstate. In February of that year, the Trump-Zelensky relationship hit its lowest point during an Oval Office meeting that, by multiple accounts, devolved into a confrontation over gratitude. Vice President JD Vance demanded Zelensky say "thank you" for American assistance. The session blew up. Officials escorted the Ukrainian president out before a planned luncheon could take place.
The fallout lingered for months. Last year, when retired Lt. Gen. Keith Kellogg, then Trump's envoy to Ukraine, praised Zelensky as an "embattled and courageous leader," Trump called Kellogg an "idiot" for saying it.
Now the president is using similar language himself. During an Oval Office visit with NATO Secretary General Mark Rutte roughly two weeks before the summit, Trump said of Zelensky: "You have to say he's courageous. He's got great equipment, he's got great men, he's got fighters."
The turnaround has a simple explanation, and Kellogg supplied it bluntly. He told the Post on Wednesday:
"Because Zelensky is winning."
Kellogg went further, describing a president whose view of the war has shifted as the ground realities changed. Ukraine's forces have been eliminating roughly 35,000 Russian troops each month, officials said, a rate Moscow reportedly cannot sustain by backfilling new recruits.
Kellogg told the Post that Trump had been told Putin was winning, and had believed it. That is no longer the case.
"Zelensky's putting the pressure on the Russians, and I think the President now realizes this guy, Putin, who may be a nice guy with you, but basically, he's not winning the war."
Kellogg added, paraphrasing Trump's evolving calculus: "People have told him Putin's winning, he's been thinking he's winning, he's not. Now Trump realizes, 'well, maybe I'm on the wrong horse right now.'"
An unnamed source with knowledge of the growing relationship between the two leaders put it more simply: "Everyone knows the president loves winners. And right now, Ukraine is winning."
The administration's posture has been consistent on this front in recent days. On Monday, Vance told The Times of London that Russia's offensive has largely stalled. Trump's willingness to recalibrate on foreign policy when circumstances shift, whether in the Middle East or Eastern Europe, has been a recurring feature of his second term.
"Frankly, the Russians are in a place right now where the amount that they can get through continued offensive operations is vanishingly small, and getting close to zero. That very well may create the space that we need to bring this thing to a close."
The most tangible result of the improved relationship came when Trump, seated beside Zelensky before reporters, floated the Patriot manufacturing license. He framed it with characteristic informality.
"A little birdie told me this, about the fact that we'll give them the right to make Patriots."
Then, turning to Zelensky with a grin: "This way, you can't complain that we're not giving them enough."
If finalized, the license would make Ukraine just the fourth foreign country, joining Japan, Germany, and Poland, with a license or preliminary approval to produce Patriot interceptor missiles. The Biden administration had refused to extend such a license, making the offer a clear departure from previous policy.
The precise terms and timeline for Ukraine to begin manufacturing remain unclear. Whether the license has been formally signed or remains in a discussion phase was not specified. But the public pledge, made in front of cameras at a NATO summit, carries diplomatic weight regardless.
The broader pattern of Trump using high-profile bilateral meetings to make bold announcements has been a hallmark of his approach to foreign leaders, putting the other party on the spot, publicly, in a way that locks both sides into forward motion.
NATO Secretary General Mark Rutte appears to have played a background role in the diplomatic thaw. During his Oval Office visit roughly two weeks before the summit, Rutte was present when Trump praised Zelensky's courage and military capability.
Rutte told the Post last month that Trump had come around on Ukraine's battlefield performance: "I think what the president also acknowledged... is that the Ukrainians are doing quite well."
That assessment aligns with what Kellogg and Vance have said publicly. The administration seems to have reached an internal consensus, or at least a working agreement, that Russia's position has weakened enough to change the diplomatic equation.
The consistency across multiple senior officials is notable. When the White House has pushed back on reports of internal disagreements over foreign policy, the Trump-Zelensky rapprochement offers an example of the administration moving in a unified direction.
Trump also said he is willing to visit Ukraine "at the right time", a statement that would have been nearly unthinkable in the months after the February 2025 blowout. A sitting American president traveling to an active war zone carries enormous security and symbolic weight.
No date or conditions were specified. But the willingness itself signals how far the relationship has traveled.
The summit did produce one awkward moment: Trump accidentally referred to Zelensky as "President Putin," then recovered by noting he would have a call with Putin later. The gaffe drew attention but did not derail the broader tone of the meeting.
The episode is a reminder that personal diplomacy at this level is messy, unpredictable, and sometimes embarrassing, but it is also where deals get made. People who once doubted Trump's ability to navigate these relationships have had reason to reconsider more than once.
Several questions hang over the summit's most significant announcement. The 35,000 monthly Russian casualty figure cited by unnamed officials has not been independently verified in the available reporting. The identities of those officials were not disclosed.
The Patriot manufacturing license itself raises practical questions. How quickly could Ukraine stand up production? What technology-transfer arrangements would be required? And would the license survive a future change in battlefield dynamics or a ceasefire negotiation?
Kellogg's characterization of Trump's evolving view, "maybe I'm on the wrong horse right now", was presented inside quotation marks as Kellogg's paraphrase of the president's thinking, not as a direct Trump quote. The distinction matters. It reflects Kellogg's interpretation of a shift, not necessarily Trump's own private language.
And the summit's location itself went unspecified in the Post's reporting, an unusual omission that leaves the precise diplomatic setting undefined.
The Trump-Zelensky relationship has been one of the more volatile diplomatic pairings of the past two years. It started with a phone call that triggered Trump's first impeachment. It cratered in the Oval Office in February 2025. Now it appears to have stabilized around a shared interest: Ukraine is performing well on the battlefield, and Trump wants to be associated with that performance.
That is not sentimentality. It is strategic recalibration. Trump has shown repeatedly, on domestic policy and foreign affairs alike, that he responds to results, not loyalty tests or diplomatic niceties.
Zelensky, for his part, appears to have learned the same lesson. He showed up, sat down, and let the battlefield do the talking.
In Washington and at NATO, winning still counts for something. The leaders who figure that out tend to get the next meeting, and the next deal.