Trump has his old friend Steve Witkoff leading his toughest diplomatic talks

President Trump’s envoy Steve Witkoff is in Oman on Saturday for nuclear talks with Iran‘s foreign minister, a day after talks in Moscow to try to broker a deal with Russian President Vladimir Putin to end the war in Ukraine.

Witkoff — whose background is in New York real estate — has also been the lead player in trying to reach a ceasefire in Gaza.

Managing talks about the three conflicts would be a massive portfolio for the most veteran of diplomats. But this is Witkoff’s first foray into international diplomacy — and that has worried policy experts in the field.

“My concern is and I think the concern of lots of others is that the president and Mr. Witkoff see Iran nuclear negotiations or a ceasefire agreement in Gaza as very similar to a negotiating real estate deal. And they’re very, very different,” said Steven Cook, a senior fellow for the Middle East at the Council on Foreign Relations.

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 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

Once in office, 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.

A lot of experts scoffed at Kushner’s lack of experience when he started his White House role, and some are raising the same questions about Witkoff.

Aaron David Miller, a former State department negotiator in both Democratic and Republican administrations, has been part of numerous Arab-Israel talks. He acknowledges the challenges and says they lost more than they won.

He said the three conflicts Witkoff is tasked with are “galactic challenges” where the complexities and differences between those involved are “as wide as the Grand Canyon.”

“I mean, you can’t do this stuff on the back of a cocktail napkin,” said Miller who is now at the Carnegie Endowment for International Peace.

“I think it’s very hard to task one individual — as talented as he may be — and make him the envoy for everything,” Miller said.

How Witkoff describes his approach to negotiations

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.

“His results speak for themselves, including the release of Marc Fogel from Russia and hostages trapped in Gaza,” said spokeswoman Anna Kelly. “The president is incredibly proud of all Mr. Witkoff has accomplished to help restore peace through strength, and he will continue to leverage Mr. Witkoff’s talents to advance his America First foreign policy vision.”

Witkoff fueled some criticism recently after appearing on Tucker Carlson’s podcast when he described Russian President Vladimir Putin as “not a bad guy.”

In the 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 said he has seen that attitude first-hand 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, a real estate developer 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.”