Steve Witkoff, flanked by President Trump, speaks at the White House on May 28.
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President Trump is defending Steve Witkoff, his special envoy, after a leaked recording appeared to show him coaching a Russian official on how to better sell Moscow’s terms to end the war with Ukraine to the U.S. president.
Trump dismissed any 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 shined a new spotlight on Witkoff, the president’s long-time friend and chief negotiator who has drawn criticism for his lack of experience and go-it-alone style.
The recording is of an October call in the lead up to the release of the original 28-point plan to end the war in Ukraine that favored Russia.
Bloomberg reviewed audio of the call and published a transcript. NPR has not independently verified the transcript or call audio.
Trump said Tuesday night he hadn’t heard the audio, but also did not have a problem with the characterization of the call.
“You got to say, ‘look, they want this. You’ve got to convince them with this. You know, that’s a very standard form of negotiation,” he said.
The criticism has been blunt: That Witkoff is not looking for a balanced deal, but carrying water for Russia — a U.S. adversary and the aggressor in a war versus Ukraine, a strategic partner and European ally.
But Trump doesn’t seem too concerned. He’s sending Witkoff back to Moscow to try to finalize details of the latest plan with Putin.
Trump and Witkoff have a long friendship
Witkoff and the president have been friends for almost 40 years. Trump calls Witkoff “a special guy” and “my pal.” Their friendship dates back to a chance encounter at a New York Deli at 3 a.m.
Trump had no cash on him. “I ordered him a ham and swiss,” Witkoff said, according to a report in Courthouse News about his testimony in Trump’s defense during one of Trump’s trials last year.
Witkoff said in an interview with Tucker Carlson that he learned the real estate business from Trump.
“I wanted to be him,” Witkoff said. “Everybody wanted to be him. He’d come to 101 Park Avenue, where I was a lawyer. He had this swashbuckling style. I used to see him come in and I used to say, ‘God, I want to be him.'”
Witkoff has described how Trump was there for him when one of his sons died from an opioid overdose in 2011.
“I have seen his humanity in the quiet moments away from the spotlight in hospital rooms he didn’t have to be in — where his presence brought real solace in a dark hour for my family,” Witkoff said at the Republican National Convention.
During the campaign, Witkoff helped with fundraising. Trump also turned to Witkoff to handle sensitive matters like trying to repair ties with Georgia Gov. Brian Kemp and presidential primary challenger Nikki Haley.
“His best friend, Steve Witkoff, came to our house in South Carolina, spoke to me and my husband, and basically wanted a truce between me and Donald Trump,” Haley said on her podcast. She told Witkoff that Trump had her support.
Picking Witkoff for a role his son-in-law used to fill
Well before assigning him the Ukraine peace deal, Trump picked his old friend as his envoy to the Middle East.
It was the same position that Trump — in his first term — had given to another person whose loyalty was unquestioned: his son-in-law, Jared Kushner.
Kushner, who now runs an investment firm, had also come from the real estate world and handled many tough files for Trump, including Middle East peace, trade talks with Mexico and Canada, immigration reform and parts of the administration’s response to the COVID pandemic.
In President Trump’s first term, his son-in-law Jared Kushner held the role now filled by Steve Witkoff. Kushner and Witkoff appeared together on Feb. 20 at a Miami conference organized by the non-profit arm of Saudi Arabia’s main sovereign wealth fund called the Future Investment Initiative (FII) Institute.
A lot of experts scoffed at Kushner’s lack of experience when he started his White House role, and some raised the same questions about Witkoff.
How Witkoff describes his approach to negotiations
The White House has described Witkoff as a trusted friend of the president who left behind a massive business enterprise to serve the country. He doesn’t take a salary and pays for his own travel.
Witkoff is certainly no stranger to creating some Russia-related controversy.
Earlier this year, Witkoff raised eyebrows after appearing on Tucker Carlson’s podcast and said Putin was “not a bad guy.”
In the same interview, Witkoff explained his approach to negotiations. “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,” he said.
Don Peebles, the real estate entrepreneur, told NPR this spring that he had seen that attitude firsthand during adversarial talks with Witkoff.
“If I were going to summarize his approach is to find what the other person, other side, wants — and to try to give it to him,” said Peebles, who fundraised for former President Barack Obama.
Peebles said he thinks Witkoff probably has more high stakes negotiating experience than most diplomats.
He remembers being forced to deal with Witkoff on a big real estate transaction in New York. Peebles considered walking away. He felt like he had a gun to his head, but never by Witkoff.
Witkoff defused the situation, promising not to be disruptive and explained how they would both be better off as partners, Peebles recalled.
“He took a very adversarial situation from my perspective and not only got the deal done, but we’ve been friends ever since.”
War in Ukraine is not the same as a real estate deal
But solving the war in Ukraine is incredibly complex.
Even negotiating giants such as Secretaries of State Henry Kissinger and James Baker would have a tough time convincing Putin to lay down his arms, according to Aaron David Miller, who has served as a negotiator and analyst for both Republican and Democratic administrations.
“Deals are cut when there is urgency,” said Miller, who is now at the Carnegie Endowment for International Peace. “And urgency is a function of two things: How much pain the parties are under and what are the prospects for gain right now.”
Miller said that urgency requires a mediator who is prepared “to use honey and vinegar,” or incentives and disincentives to produce something that both Putin and Zelensky will be able to rationalize — as well as sell to their own people.
“I just don’t see Putin ready to make the kinds of concessions that would be required to anchor this thing and make it work,” Miller said.
