Steve Witkoff, flanked by President Trump, speaks at the White House on May 28. Andrew Harnik/Getty Images
President Trump is defending Steve Witkoff, his special envoy, after a leaked recording appeared to show Witkoff coaching a Russian official on how to better sell Moscow’s terms to end the war in Ukraine to the U.S. president. Trump dismissed concerns as “a standard thing.”
“Because he’s got to sell this to Ukraine. He’s got to sell Ukraine to Russia,” Trump said aboard Air Force One, on his way to Florida. “That’s what a dealmaker does.”
The controversy has focused attention on Witkoff, the president’s longtime friend and chief negotiator, who has faced criticism for his lack of diplomatic experience and a go-it-alone style. The recording, from an October call ahead of the release of a 28-point plan that favored Russia, was reviewed by Bloomberg, which published audio and a transcript; NPR has not independently verified the material. Trump said he had not heard the audio but did not object to the characterization of the call, calling the alleged coaching a normal negotiating tactic.
Critics argue Witkoff appears to be carrying water for Russia — an adversary and the aggressor in the war — rather than seeking a balanced resolution for Ukraine, a strategic partner and European ally. Despite the scrutiny, Trump is sending Witkoff back to Moscow to try to finalize details of the latest plan with Putin.
Witkoff and Trump have been friends for almost 40 years. Trump has called Witkoff “a special guy” and “my pal.” Their friendship reportedly began with a chance encounter at a New York deli when Trump paid for a ham and Swiss sandwich Witkoff couldn’t afford. Witkoff testified in Trump’s defense during one of the former president’s trials and has said he learned the real estate business from Trump, telling an interviewer he once wanted to be like him.
Witkoff has been publicly supportive of Trump and took on sensitive roles during the campaign, including fundraising and trying to repair ties between Trump and political figures such as Georgia Gov. Brian Kemp and former primary challenger Nikki Haley. Haley has said Witkoff visited her home in South Carolina to broker a truce and indicated she would support Trump.
Before being assigned the Ukraine portfolio, Trump named Witkoff as an envoy to the Middle East — a slot once held by Jared Kushner in Trump’s first term. Kushner, like Witkoff, came from the real estate world and handled several high-profile and unconventional foreign-policy tasks for Trump. Critics who questioned Kushner’s experience raised similar concerns about Witkoff.
The White House presents Witkoff as a trusted friend who left a large business enterprise to serve without salary and who pays his own travel. Witkoff has at times generated controversy for comments about Russia; earlier this year he told Tucker Carlson that Putin was “not a bad guy.” In that same interview he described his negotiating philosophy: “There’s no doubt I’m always trying to put myself in the shoes of the other person because a good deal has to work fair for everybody.”
Don Peebles, a real estate entrepreneur who has dealt with Witkoff, told NPR he has seen that approach firsthand. Peebles said Witkoff seeks to identify what the other side wants and find a way to give it, and recalled a tense New York real estate negotiation where Witkoff defused the situation and turned adversaries into partners.
But several analysts warn that brokering an end to the war in Ukraine is far more complex than a business deal. Aaron David Miller, a longtime negotiator and analyst now at the Carnegie Endowment for International Peace, noted that even seasoned diplomatic giants would struggle to get Putin to make the concessions needed for a durable settlement.
“Deals are cut when there is urgency,” Miller said. “And urgency is a function of two things: How much pain the parties are under and what are the prospects for gain right now.” Successful mediation, he added, often requires a mix of incentives and disincentives — “honey and vinegar” — that produce terms both leaders can rationalize and sell to their publics. Miller expressed skepticism that Putin is prepared to make the necessary concessions to anchor a workable deal.
As the debate continues over Witkoff’s approach and the leaked call, Trump has signaled continued confidence in his friend and envoy, instructing him to return to Moscow to advance the negotiations despite criticism from opponents and some foreign-policy experts.