As the war in Ukraine continues, scrutiny intensifies on diplomatic efforts undertaken during the Trump management. A new report details stark contrasts in the engagement of former Special Envoy Steve Witkoff with officials in Kyiv and Moscow, raising questions about the priorities guiding U.S. foreign policy at the time. Leaked recordings and eyewitness accounts reveal a markedly different approach to negotiations, one characterized by apparent deference to Russian interests and unconventional diplomatic practices.
The dynamic between a U.S. delegation and Ukraine contrasted sharply with interactions held by a Trump administration envoy in Moscow, raising questions about priorities and allegiances as the conflict continues. The meetings highlight the complex diplomatic landscape surrounding the war and the role of individuals with deep ties to both sides.
During a meeting with Ukrainian officials in Miami, Steve Witkoff, then-President Trump’s special envoy for Ukraine, appeared visibly disengaged. Witnesses described him as unshaven, somber, and avoiding eye contact throughout the discussions. The atmosphere in Moscow, however, was markedly different.
While appearing strained during the meeting with the Ukrainian delegation, Witkoff appeared revitalized in Moscow. Seated across from President Vladimir Putin, he was seen smiling, cleanly shaven, and attentively engaged. He told Putin he had enjoyed a “beautiful walk around Moscow, which is a magnificent city.”
Witkoff’s remark followed a tour of Moscow landmarks with Jared Kushner, then-President Trump’s son-in-law, and Kirill Dmitriev, an advisor to Putin. Prior to the meeting, the group dined at one of Moscow’s finest restaurants near the Kremlin, enjoying a meal of red caviar, buckwheat-stuffed quail, game meats, and crab cakes.
A Russian Heritage
The source of Witkoff’s apparent affinity for Russia lies in his family history. His original family name was Vitkov, revealing his Russian roots. His grandfather, David (1892-1970), a Jewish tailor, emigrated from the Soviet Union to the United States. Witkoff’s father, Martin, was born in the U.S. and worked as a manufacturer of women’s coats in New York.
There is no record of Steve Witkoff, born in the Bronx in 1957, previously expressing an interest in the land of his ancestors. Indeed, Trump himself acknowledged that his advisor “didn’t know much about Russia or Putin” when initial negotiations began regarding a potential peace agreement for Ukraine.
Witkoff, a real estate developer, investor, and attorney specializing in property, first befriended Trump through the real estate industry. He worked at the New York law firm Dreyer & Traub, where Donald Trump was a client. Their business relationship and shared interest in golf eventually led to a foray into politics.
During his first term, Trump appointed Witkoff to his economic advisory council. In his second, he became a special envoy for the Middle East, and later an informal but influential envoy for negotiations with Russia – a role that reportedly raised eyebrows in Washington.
A Meeting with Putin Without an Interpreter
Witkoff reportedly conducted a meeting with Vladimir Putin without an official English-language interpreter, relying instead on a Russian translator – a breach of standard diplomatic protocol. He also did not keep a record of the conversation, but instead relayed his recollections to Trump afterward.
For example, ahead of a meeting between Trump and Putin in Alaska, Witkoff misinterpreted a Russian request for the “peaceful withdrawal” of Ukrainian forces from Kherson and Zaporizhzhia as an offer for Russia to withdraw from those regions.
In an interview with controversial pro-Russian journalist Tucker Carlson in March of this year, Witkoff expressed surprising understanding towards Russian policy and its leader. He emphasized that the Russian president is “very smart” and “couldn’t be a bad person because when there was an attempt on Trump’s life, he went to church to pray for him – as a friend.” He also stated that Putin has no intention of attacking Europe and “Russia doesn’t want to absorb Ukraine.”
Witkoff also expressed confidence that Russia would be satisfied with five regions “where people speak Russian and where the majority of people in a referendum expressed a desire to live in Russia.” He was, however, unable to recall the names of all five regions.
Tell Trump He is a Man of Peace
Most recently – as revealed by leaked phone recordings – Witkoff advised Yuri Ushakov, an advisor to President Putin, on how best to appeal to Donald Trump. “I would call him and congratulate the president [Trump] for what he’s accomplished, that you support him, that he has your respect because he’s a man of peace,” he reportedly said.
Witkoff continued: “I told the president that you – the Russian Federation – have always wanted a peace deal. That’s my belief. I told the president that I believe that. I even think we could put together a 20-point peace plan, just like we did in Gaza,” he suggested.
The leaked conversation, published by Bloomberg, also suggests that Russian officials were involved in drafting a 28-point U.S. peace plan.
