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President Trump's envoy Steve Witkoff was back in Moscow today trying to broker a deal with Vladimir Putin to end the war in Ukraine. Tomorrow, he'll be in Oman for nuclear talks with Iran's foreign minister. And he's also been the lead player in trying to reach a ceasefire in Gaza. This would be a massive portfolio for a veteran diplomat, but Witkoff is a newcomer to international diplomacy. NPR White House correspondent Franco Ordoñez has more.
FRANCO ORDOÑEZ, BYLINE: President Trump calls Steve Witkoff a special guy. They've been friends for almost 40 years.
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PRESIDENT DONALD TRUMP: You know, people don't realize Steve started out as a lawyer - very good lawyer, top lawyer in New York. And then he said, I'm going to go in the real estate business 'cause I can do this, too. He saw me do it, and he said, if Trump can do it, I guess I can do it, right?
ORDOÑEZ: During the campaign, Witkoff described how Trump was there for him when one of his sons died from an opioid overdose in 2011.
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STEVE WITKOFF: I have seen his humanity in the quiet moments, away from the spotlight, in hospital rooms he didn't have to be in.
ORDOÑEZ: Once in office, Trump picked his old friend as his envoy to the Middle East. It was a surprising pick. But this was the same position that Trump, in his first term, gave to another person whose loyalty was unquestioned, his son-in-law Jared Kushner. Kushner also came from the real estate world and handled many tough files for Trump. A lot of experts scoffed at Kushner's lack of experience, and they're raising the same questions about Witkoff now.
STEVEN COOK: I'm sure that he is a very successful real estate executive, but not all negotiations and deals are the same.
ORDOÑEZ: Steven Cook is at the Council on Foreign Relations. He says Witkoff is the de facto national security adviser but worries he doesn't know enough about the history and nuance of these issues.
COOK: And my concern is - and I think the concern of lots of others is - that the president and Mr. Witkoff see Iran nuclear negotiations or, you know, a ceasefire agreement in Gaza as very similar to negotiating a real estate deal. And they're very, very different.
ORDOÑEZ: Aaron David Miller was a State Department negotiator in both Democratic and Republican administrations. He says the bigger problem is that the three conflicts Witkoff is tasked with are, quote, "galactic challenges," where the complexities and the differences between those involved are as wide as the Grand Canyon.
AARON DAVID MILLER: I mean, you can't do this stuff on the back of a cocktail napkin. And I think it's very hard to task one individual, as talented as he may be, and make him the envoy for everything.
ORDOÑEZ: The White House says Witkoff is 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. A spokeswoman, Anna Kelly, says Witkoff's successes speak for themselves, citing his work helping secure the release of American Marc Fogel in Russia and hostages trapped in Gaza.
Witkoff fueled some criticism recently after appearing on Tucker Carlson's podcast. Witkoff described Russian President Vladimir Putin as, quote, "not a bad guy." In the interview, Witkoff explained his approach to negotiations.
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WITKOFF: Well, 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 for everybody.
ORDOÑEZ: Don Peebles has seen that firsthand in adversarial talks with Witkoff.
DON PEEBLES: If I were going to summarize his approach, it's to find what the other side wants and to try to give it to them.
ORDOÑEZ: Peebles is a real estate developer who fundraised for former President Barack Obama. He says 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: It was a major building project, and his benefactor, if you will, I needed them. And so it was almost like they had a gun to my head. But Steve never pointed a gun to my head, and he defused the situation and got me to get over it.
ORDOÑEZ: And not only did they get the deal done, but they've been friends ever since, Franco Ordoñez, NPR News, the White House.
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