Trump and Zelensky at Loggerheads Despite Oslo Peace Talks

Russian missile strikes on Kyiv have increased in frequency, with civilians facing reduced early warning capability due to alleged US intelligence restrictions.
Carrots for Russia, sticks for Ukraine
How a former US ambassador to Kyiv described the pattern of Trump administration policy this month.
Mark

So what's actually changed between these two in the past ten days? They've always been tense.

Mimi

Trump made a deal with Putin to open US markets to Russian diesel, then waived sanctions that were about to hit Russia. He's also slowed down Patriot missiles and allegedly cut off intelligence sharing. It's a pattern.

Luke

But wait—the diesel deal was framed as domestic politics, right? Lowering gas prices before midterms. How much of this is actually about Ukraine versus Trump's own political calendar?

Mimi

That's the thing. Even if the motive is domestic, the signal to Kyiv is unmistakable: we're willing to deal with Moscow, and we're unhappy with your strikes on Russian oil.

Mark

And the Patriot missiles—is that actually a Trump decision or just supply chain reality?

Luke

The source says global shortage, but also that the Trump administration slowed the approval process for allies to transfer their stocks. That's a choice, not a constraint.

Mimi

Right. And the intelligence sharing—Rubio says it was a software glitch, but Zelensky says they didn't get warnings for three days during ballistic attacks. That's people in Kyiv without sirens.

Mark

So is Trump actually trying to force Ukraine to negotiate, or is he just punishing Zelensky personally?

Luke

The source doesn't really separate those. It's both happening at once. But the personal history matters—Trump's never forgiven Zelensky for refusing to investigate Biden in 2019.

Mimi

And now Trump's in power again, and Zelensky is dependent on him. That's the asymmetry.

Mark

So what does the Oslo meeting actually accomplish?

Luke

Witkoff's taking proposals to Putin next. That's where the real signal will come from. If Putin gets what he wants, we'll know which way this is heading.

Mimi

Zelensky left sounding optimistic, but he has to. He's got no other choice.

  • Trump publicly called Zelensky 'not a good guy' and dismissed his judgment on a Russian diesel deal, signaling to the world that the US-Ukraine relationship has curdled into something closer to managed contempt.
  • Washington waived sanctions on Russia, slowed Patriot missile deliveries to a near-empty stockpile, and allegedly restricted satellite intelligence — all while Russian drones and missiles struck Ukrainian cities with increasing frequency.
  • Five Russian S-400 missiles hit Kyiv before air raid sirens sounded on October 12, a failure Zelensky linked directly to the alleged pause in US early warning intelligence, putting civilian lives at the center of the diplomatic dispute.
  • Zelensky has largely held his tongue, knowing his country's survival depends on American support, but his frustration finally surfaced in remarks to a congressional delegation about 'decisions hard to explain between friends.'
  • Trump's envoy Witkoff is now heading to St. Petersburg to present proposals to Putin, a visit that will reveal whether Washington is brokering peace or quietly repositioning itself toward Moscow.
  • After Oslo, Zelensky offered cautious optimism about early warning restoration and Patriot supplies, but the fragility of that hope was unmistakable — a diplomatic courtesy extended across a widening gulf.

In the shadow of an unresolved war, the alliance between Washington and Kyiv has entered a period of visible strain — not through rupture, but through the slow accumulation of slights, delays, and bargains that each side reads differently. Donald Trump and Volodymyr Zelensky met by proxy in Oslo this week, their envoys exchanging gestures of goodwill even as the substance of American policy — waived sanctions, slowed missiles, questioned intelligence — told a different story. What is being negotiated now is not merely a ceasefire, but the meaning of partnership itself, and whether the United States still regards Ukraine's survival as a cause worth the cost of antagonizing Moscow.

In Oslo this week, Trump's envoy Steve Witkoff embraced Zelensky before their talks, and Zelensky posted the moment online as a symbol of partnership. But no gesture could undo the ten days that preceded it — a cascade of decisions that left Ukraine's president wondering whether Washington still considered him an ally at all.

Trump told Newsmax that Zelensky was 'not a good guy for us to deal with,' and when asked about Ukraine's position on a Russian diesel deal, dismissed him outright. Zelensky, dependent on American support and aware of it, mostly held back — but his restraint broke when he told a congressional delegation there were 'decisions on the American side that are hard to explain between friends,' and pushed back on Trump's claim that he was the main obstacle to peace.

The policy moves behind the rhetoric were more alarming than the words. As Ukrainian negotiators arrived in Miami for talks with Trump's team, the president announced a deal to open US markets to Russian diesel — framed as relief for American consumers, but read in Kyiv as a reward for Moscow. Two days before congressionally mandated sanctions on Russia were set to take effect, Trump waived them, saying they would complicate peace efforts. A former US ambassador to Kyiv summarized the pattern to the BBC: carrots for Russia, sticks for Ukraine.

Patriot interceptors had slowed to what one Ukrainian official described as just a couple of units remaining in stockpile. Allegations — denied by US officials — emerged that Washington had also restricted satellite intelligence and interfered with Starlink access. The damage was not abstract: on October 12, five Russian missiles struck Kyiv before air raid sirens sounded, a failure Zelensky attributed to missing American early warning data. Secretary of State Rubio blamed a software glitch.

The mistrust has older roots. Trump has long believed, without evidence, that Ukraine interfered in his 2016 campaign. His 2019 phone call pressing Zelensky to investigate Biden — while $391 million in military aid was being withheld — led to his first impeachment. Whether that grievance still shapes his Ukraine policy is uncertain. What is certain is that the relationship has lurched downward again.

After Oslo, Zelensky said the early warning issue had been resolved and expressed hope about Patriot supplies and Starlink. Witkoff departed for St. Petersburg to present proposals to Putin. The optimism felt thin — a courtesy extended across a relationship that has rarely been more uncertain, at a moment when the stakes for Ukraine, Europe, and the post-war order could not be higher.

In Oslo this week, Steve Witkoff, Donald Trump's envoy, embraced Volodymyr Zelensky before their scheduled talks. Zelensky posted the moment to social media with a message about working for peace and thanking partners for their support. The gesture was meant to signal alignment. But the hug could not undo what had happened in the ten days prior—a cascade of decisions and statements that had left the Ukrainian leader questioning whether the American president still regarded him as anything resembling an ally.

The two men have never been comfortable with each other. Their relationship has always carried friction. But this month the temperature dropped sharply. Trump told Newsmax that Zelensky was "not a good guy for us to deal with." When a reporter asked his view of Zelensky's position on a proposed diesel deal with Russia, Trump dismissed him outright: "Zelensky doesn't know what he's talking about." These are not the words of a patient negotiator. They are the words of someone signaling displeasure to an audience. Yet with Trump, such rhetoric can be difficult to parse. In June he had attacked Israel's prime minister with crude language, only to reverse course four months later and call him a great warrior. As one analyst at the Centre for European Reform noted, Trump could always execute another reversal. But this, he added, looked bad.

Zelensky, by contrast, had mostly restrained himself. He is dependent on American support and knows it. But this month his frustration broke through. Speaking to a congressional delegation, he referenced "decisions on the American side that are hard to explain between friends" and voiced a fear that political calculations in Washington had led to a deliberate slowdown in aid. When Trump accused him of being the main obstacle to peace, Zelensky responded with visible exasperation, writing on Telegram that Ukraine had welcomed "literally EVERY attempt" by partners to end the war with dignity.

The substance behind the rhetoric was alarming. Earlier this month, as Ukrainian negotiators arrived in Miami to meet with Trump's envoys, the president announced a deal with Vladimir Putin to open American markets to Russian diesel. The move was framed as a way to lower US petrol prices ahead of congressional elections, but to Kyiv it read as a signal: Washington was willing to strike bargains with Moscow, and it was displeased with Ukraine's campaign of long-range strikes on Russian oil refineries. Two days before sanctions on Russia were set to take effect under legislation named after the late senator Lindsey Graham—a vocal Ukraine supporter—Trump waived them. He said the sanctions would complicate his peace efforts. For Ukraine and its backers, it was another indication that the White House was tilting toward the Kremlin. A former US ambassador to Kyiv told the BBC the pattern was clear: carrots for Russia, sticks for Ukraine.

The restrictions on military aid compounded the damage. Patriot air defense missiles, desperately needed to intercept Russian ballistic missiles, had slowed to a trickle due to global shortages and what Ukrainian officials described as deliberate delays by the Trump administration in approving transfers from American allies. According to the Washington Post, citing an unnamed Ukrainian official, only a couple of Patriot interceptors remained in Ukraine's stockpile. Separately, allegations emerged—unconfirmed by US officials—that the administration had restricted the flow of American satellite intelligence and interfered with Ukraine's access to Elon Musk's Starlink satellite internet. The timing was particularly damaging. Russia had escalated its drone and missile campaign against Ukrainian cities. On October 12, five Russian S-400 missiles struck Kyiv reportedly before air raid sirens sounded, a failure Zelensky attributed to missing early warning from US intelligence. When asked about the intelligence pause, Secretary of State Marco Rubio blamed a software problem. On Starlink, he denied any White House order to throttle service. Yet the frequency with which such suspicions surfaced pointed to a deeper erosion of trust.

The roots of Trump's mistrust run deep. A decade ago, he had become convinced Ukraine interfered in his 2016 campaign, a belief without foundation. When Zelensky became president, Trump pressed him to investigate election interference claims. During a July 2019 phone call, Trump also asked Zelensky to investigate Joe Biden. Zelensky refused both times. The White House was withholding $391 million in military assistance at the moment of that second request—a juxtaposition that led to Trump's first impeachment. Whether that resentment still shapes his current policy is unclear. What is clear is that the relationship has lurched downward again.

After the Oslo talks, Witkoff was heading to St. Petersburg to present updated proposals to Putin. Norway's prime minister said the discussions had helped "straighten out a few things." Zelensky indicated that the early warning issue had been resolved and expressed optimism about Patriot supplies and Starlink access. "I think we will have good results too," he said. Yet the optimism felt fragile, a diplomatic courtesy extended in a moment of deep uncertainty. Zelensky and Trump appeared once again to be at odds, and the stakes—for Ukraine, for Europe, for the shape of the post-war order—could not be higher.

What the Trump administration is doing is providing carrots to the Russians and sticks to the Ukrainians. It's inexplicable and saddening.
— William Taylor, former US ambassador to Kyiv, speaking to the BBC
We have welcomed literally EVERY attempt by our partners to end this war with dignity.
— Volodymyr Zelensky, responding to Trump's charge that he was the principal obstacle to negotiated settlement
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