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Why Does Steve Witkoff Keep Taking Russia’s Side?

By Eric November 27, 2025

In a revealing turn of events surrounding the ongoing conflict between Russia and Ukraine, Steve Witkoff, a former real estate developer turned negotiator, appears to have played a pivotal role in influencing U.S. foreign policy. On October 14, Witkoff engaged in a conversation with Yuri Ushakov, a senior Russian official, where he suggested that Russian President Vladimir Putin should call President Donald Trump. This call, which took place on October 16, reportedly lasted over two hours and led to a significant shift in Trump’s stance on military support for Ukraine. Just a day later, during a meeting with Ukrainian President Volodymyr Zelensky, Trump refrained from offering Tomahawk missiles to Ukraine, a decision that some analysts believe may have been swayed by Witkoff’s recommendations to Ushakov.

Witkoff’s actions raise critical questions about his motivations and the implications for the war. While he is ostensibly negotiating a peace settlement on behalf of the United States, his advice to Ushakov—to flatter Trump and emphasize Russia’s desire for a peace deal—seems to align more with Russian interests than with those seeking a genuine resolution to the conflict. This dynamic is further complicated by Witkoff’s lack of diplomatic experience and his potential business ties to Russia, which may influence his perspective. Critics argue that instead of facilitating a pathway to peace, Witkoff’s interventions may inadvertently prolong the war, emboldening Russia to pursue its territorial ambitions while undermining Ukrainian sovereignty.

The broader context of these events highlights a troubling reality: the war in Ukraine will only cease when Russia decides to halt its aggression and recognize Ukraine’s sovereignty. The ongoing conflict has resulted in immense suffering, and the Ukrainian government has expressed willingness to agree to a cease-fire based on current lines of conflict. However, Witkoff’s approach seems to advocate for concessions from Ukraine rather than pressuring Russia to withdraw. This strategy, if pursued further, could lead to a temporary cessation of hostilities while positioning Russia for future aggression. The situation underscores the urgent need for a recalibrated U.S. foreign policy that prioritizes the sovereignty of Ukraine and the security of Europe, rather than appeasing Russian demands. As the conflict continues to unfold, the world watches closely to see whether Witkoff’s influence will ultimately facilitate peace or contribute to further escalation.

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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