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Why Does Steve Witkoff Keep Taking Russia’s Side?

By Eric November 29, 2025

In a recent analysis, the complex and controversial role of Steve Witkoff in the ongoing Russia-Ukraine conflict has been scrutinized, particularly regarding his influence on U.S. foreign policy. Witkoff, a former real estate developer with no prior diplomatic experience, has been tasked with negotiating a peace settlement between Russia and Ukraine, ostensibly on behalf of the United States. However, the timing of his discussions with Russian official Yuri Ushakov raises questions about his true intentions and the implications for the war in Ukraine. On October 14, Witkoff advised Ushakov that Russian President Vladimir Putin should reach out to President Donald Trump, which led to a lengthy phone call on October 16. This conversation reportedly altered Trump’s stance on potentially supplying Ukraine with Tomahawk missiles, a significant military aid that could have bolstered Ukraine’s defense against Russian aggression.

The fallout from this interaction is notable, as Trump refrained from offering military support during a meeting with Ukrainian President Volodymyr Zelensky just a day later. Instead, Trump suggested that Ukraine concede territory in Donetsk to Russia, aligning with longstanding Kremlin demands. This maneuver indicates a troubling shift in U.S. policy, potentially emboldening Russia while undermining Ukraine’s sovereignty. Witkoff’s influence appears to extend beyond mere negotiation tactics; his actions may inadvertently prolong the conflict by fostering an environment where Russia feels it can achieve its objectives without facing significant pushback from the U.S. or its allies. Critics argue that Witkoff’s approach reflects a dangerous naivety or even a misguided loyalty to Putin, which could have dire consequences for the millions affected by the ongoing war.

The implications of Witkoff’s involvement extend far beyond diplomatic discussions, as they may facilitate further Russian aggression. Experts emphasize that true peace can only be achieved when Russia ceases its military operations and acknowledges Ukraine’s sovereignty. Witkoff’s advocacy for a peace plan that could serve Russian interests, rather than pressing for accountability and a cessation of hostilities, raises alarm bells about the future of U.S.-Ukraine relations. As the situation unfolds, the necessity for a clear and firm U.S. stance against Russian expansionism becomes increasingly critical. The ongoing conflict in Ukraine is a humanitarian crisis, and any actions that prolong the war only exacerbate the suffering of countless individuals caught in the crossfire.

https://www.youtube.com/watch?v=katXmNtOEnc

Pay attention to the dates, because the timing matters. Steve Witkoff
spoke
with Yuri Ushakov, a Russian official, on October 14. Ukrainian President Volodymyr Zelensky held a meeting with President Donald Trump in Washington, D.C., on October 17. Trump had been hinting that he would offer to sell Tomahawks, long-range cruise missiles, to the Ukrainian army. But he did not.
Why not? Perhaps because Ushakov listened to Witkoff’s advice and persuaded Russian President Vladimir Putin to call Trump on October 16. Witkoff, in other words, may have helped block that sale. And that would make Witkoff responsible for prolonging the war.
Let me back up and explain.
Witkoff, a former real-estate developer, is supposed to be negotiating a peace settlement between Russia and Ukraine. He is in theory acting on behalf of the United States but also on behalf of millions of people who want peace in Ukraine and security in Europe. Ushakov, a former Russian ambassador to the United States, has different interests: Like his boss, he wants Russia to win the war.
[
Read: Trump’s real secretary of state
]
A tape of the October 14 conversation has been
leaked to
Bloomberg
. That’s how we know Witkoff suggested to Ushakov that Putin call Trump. He also offered advice about what Putin should say. The Russian leader should flatter Trump, of course, which is standard advice for speaking to the American president: “Compliment him on his great success in Gaza, congratulate the president on this achievement.” After that, Witkoff said, “It’s going to be a really good call.”
Then, Witkoff advised, Putin should impress upon Trump this idea: “The Russian Federation has always wanted a peace deal. That’s my belief. I told the president I believe that.” Together, the two of them would cook up a peace plan, just like Trump’s recent Gaza peace plan.
Ushakov gave Putin this advice. Putin followed it. How do we know? Because Putin did, in fact, call Trump, on October 16. The call lasted for
more than two hours
. Trump said the call was productive, and that the two leaders would soon meet, potentially in Budapest (which never happened). During his meeting with Zelensky on the following day, he did not offer Tomahawk missiles to Ukraine. Instead, he became emotional and angry.
In keeping with a long-standing Russian demand, Trump tried to persuade the Ukrainians to give up Ukrainian land in Donetsk province that they currently control—land that the Russians have not been able to conquer after more than a decade of fighting. This is what Putin wants: to obtain Ukrainian territory without fighting for it, to weaken Ukraine, and to use any temporary cease-fire as an opportunity to plan the next invasion.
“With a single phone call,” one insider
told
Politico
last month
, “Putin appears to have changed President Trump’s mind on Ukraine once again.” This was Witkoff’s achievement. Working with another Kremlin insider, Kirill Dmitriev, he went on last week to
propose the 28-point peace plan
that could, if carried out, temporarily stop the fighting but position Russia to invade a weakened Ukraine at a later date.
[
Anne Applebaum: The murky plan that ensures a future war
]
I’ve
written this before
, but it cannot be repeated often enough: This war will end only when Russia stops fighting. The Russians need to halt the invasion, recognize the sovereignty of Ukraine, and drop their imperial ambitions. Then Ukraine can discuss borders, prisoners, and the fate of thousands of kidnapped Ukrainian children.
But the only way to persuade Russia to stop fighting is to put pressure
on Russia
. Not Ukraine,
Russia
. The Ukrainians have already said they will stop fighting and agree to a cease-fire right now, on the current lines of conflict. Yet Witkoff is seeking to persuade Trump
not
to put pressure on Russia, and we don’t really know why.
Witkoff has no previous diplomatic experience, so perhaps he is naive. He spent many years in New York real estate, at a time when Russians were spending fortunes on property, so perhaps he feels gratitude. Maybe he’s helping Russia win because he has “the deepest respect for President Putin,” as he told Ushakov, and admires his brutality. Maybe he, or others in the White House entourage, have business interests tied to Russia—or hope to. In addition to discussing “peace,” Witkoff has also been, according to the document made public last week, talking with the Russians about American investments “in the areas of energy, natural resources, infrastructure, artificial intelligence, data centers, rare earth metal extraction projects in the Arctic.”
Whatever the reason, Witkoff is prolonging the conflict. He is not promoting peace. His call to Ushakov was not, as Trump
said last night
, a normal negotiating tactic. Every time he intervenes, advocating for Putin’s positions, he encourages the Russians to think they can get Trump on their side, pull America away from Europe, break up NATO, and win the war. In other words, every time he intervenes on behalf of the Russians, he contributes to the deaths of Ukrainians, the attacks on infrastructure, the ongoing tragedy that affects millions of people.
If this were a normal American administration, he would be fired immediately. But nothing about this negotiation, or this administration, is normal at all.

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