When President Trump appointed his friend Steven Witkoff to be his Middle East envoy last November, the choice prompted head-scratching in diplomatic circles.
Many foreign officials had never heard of Mr. Witkoff, a billionaire New York real estate developer who has known Mr. Trump since the mid-1980s. The president’s new envoy not only lacked expertise in the region apart from some business dealings, he had no diplomatic experience.
That didn’t matter to a president who considers Washington credentials a liability and views foreign policy as a series of business transactions. And Mr. Trump was impressed by Mr. Witkoff’s ability to help the outgoing Biden administration seal a temporary cease-fire deal in Gaza between Israel and Hamas.
Now, in a fresh sign of confidence in his old friend, Mr. Trump has expanded Mr. Witkoff’s portfolio. As Mr. Trump pursues a peace deal in Ukraine and a potential realignment of U.S.-Russia relations, he has tapped Mr. Witkoff to be his personal envoy to Russia’s president, Vladimir V. Putin.
On Thursday morning, Mr. Witkoff landed in Moscow to meet with the Russian leader for the second time in just over a month. In mid-February, he and Mr. Putin sat down for a three-and-a-half-hour session that led to Mr. Putin’s release of Marc Fogel, an American serving a prison sentence in Russia on marijuana smuggling charges.
Engaging Mr. Putin is an assignment that would make even a seasoned diplomat take a deep breath. Befitting his past as an intelligence operative, the Russian leader is a master of intimidation, manipulation and deceit. Some experts and diplomats who know Mr. Putin fear that Mr. Witkoff may be in over his head.
Recent signs that Mr. Witkoff may have a key role in Mr. Trump’s early diplomacy with Iran over its fast-growing nuclear program have also raised other questions, including whether Mr. Witkoff risks being stretched too thin and whether, as a kind of roving super envoy, he would chafe against the secretary of state, Marco Rubio. Mr. Rubio flew to Moscow from Doha, Qatar, where he had been helping mediate talks between Israel and Hamas to extend the fragile Gaza cease-fire.
In Moscow, Mr. Witkoff will hear Mr. Putin’s take on a Ukraine cease-fire plan that U.S. and Ukrainian officials agreed on earlier this week in Saudi Arabia. A pause in the fighting could be a first step toward Mr. Trump’s goal of quickly ending the war in Ukraine and moving to normalize relations with Russia.
The conversation does not promise to be simple: Speaking to reporters before the meeting on Thursday, Mr. Putin raised a serious of questions about the plan, which a top Kremlin aide had dismissed as “hasty.” Many analysts say that Mr. Putin has little incentive to end a war in which he now appears to have an upper hand.
If he does agree to end the war, Mr. Putin may insist on major concessions, analysts say, including an American military pullback from Eastern Europe and an explicit, Cold War-style recognition of a Russian sphere of regional influence.
Mr. Witkoff is the first senior U.S. official to meet with Mr. Putin since before Russia invaded Ukraine in February 2022. The Biden administration cut off contact with Mr. Putin and accused Russia of committing crimes against humanity in Ukraine.
Mr. Witkoff seemed to have been at ease with the Russian leader during their first meeting, saying at an investment conference in Miami last month that he had spent the session “developing a friendship, a relationship” with Mr. Putin.
The remarks are in line with others Mr. Witkoff has made disputing the idea that Russia is a dangerous aggressor.
Speaking on CNN last month, he said that Russia’s invasion of Ukraine “was provoked,” adding: “It doesn’t necessarily mean it was provoked by the Russians.”
The comment reflected the view, now common on both the far left and far right, that America forced Mr. Putin into military action by gradually expanding the NATO alliance deep into Eastern Europe, and by proposing to make Ukraine a member.
In 2018, Mr. Witkoff also criticized Western economic sanctions against Russia, imposed after it annexed Ukraine’s Crimean Peninsula in 2014 and tried to influence the 2016 U.S. presidential election. “I never understood the Russian sanctions, candidly, because all it did was stop Russian investment into this country,” he said in a podcast interview.
Such talk, along with Mr. Witkoff’s inexperience with Mr. Putin, worries some of those who know the Russian leader best.
“You need to be super well prepared” to deal with Mr. Putin, said Fiona Hill, a Putin biographer who served as Mr. Trump’s senior National Security Council director for Russia.
As a counter example to Mr. Witkoff, Ms. Hill recalled the messenger President Biden sent to Mr. Putin at a moment of crisis in late 2021: the C.I.A. director, William J. Burns.
To warn Mr. Putin that an invasion of Ukraine would draw a severe U.S. response, Mr. Biden dispatched Mr. Burns, who served as U.S. ambassador to Moscow during more than 40 years as a diplomat, had met Mr. Putin numerous times.
“Witkoff doesn’t have the experience, obviously, that someone like Burns did,” Ms. Hill said. That might matter less, she said, if he were surrounded by experts who could lend an expert ear to Mr. Putin’s commentary and offer him context and fact-checking. But she noted that Mr. Witkoff, who is operating with a bare-bones staff, had not brought anyone to his first meeting with Mr. Putin.
Expertise can be a liability to Mr. Trump, who believes that the real estate deal-making playbook is easily applied to international relations.
“It’s not as though the United States has done great over the years with experienced diplomats when it comes to Putin,” said Richard Haass, president emeritus of the Council on Foreign Relations, who said Mr. Witkoff should be given a chance to prove himself.
Similar thinking about the Middle East led Mr. Trump in his first term to task his son-in-law, Jared Kushner, who is also a real estate executive, with reaching an Israeli-Palestinian peace agreement.
In an onstage dialogue Mr. Kushner led with Mr. Witkoff at the Miami investment conference, Mr. Witkoff said it was Mr. Kushner who had convinced him to join Mr. Trump’s administration, joking that Mr. Kushner had applied “insidiously clever” tactics on him.
Mr. Kushner suggested that Mr. Witkoff’s record in real estate was more valuable on the global stage than traditional foreign policy experience.
“You come from a background of negotiations and transactions and deals, which is much different than diplomacy,” Mr. Kushner said.
People who have worked with Mr. Witkoff say he can be a tough, table-thumping negotiator. But he has an energetic, cheerful disposition and a knack for making people “feel like a million bucks,” as one Trump official put it.
Plunging into Israel’s fraught negotiations with Hamas late last year even before Mr. Trump’s inauguration, Mr. Witkoff even impressed Brett McGurk, who served as Mr. Biden’s top aide for Middle East affairs, and who was trying to broker a cease-fire in Mr. Biden’s final days.
Mr. McGurk said in an interview that he found in Mr. Witkoff a pragmatist and fellow “problem solver,” with whom he developed a close and trusting relationship. “Anything Steve is working on, is in capable hands,” McGurk said.
The expansion of Mr. Witkoff’s role to include negotiations with Moscow — Mr. Witkoff also joined Mr. Rubio and the national security adviser, Michael Waltz, in a meeting with Russian officials in Saudi Arabia last month — further muddies the question of who in the Trump administration is overseeing Russia policy.
In November, Mr. Trump named Keith Kellogg, a retired lieutenant general, to be his envoy to Ukraine and Russia. But Mr. Kellogg now appears to be playing a supporting role at best.
Mr. Trump is also interested in giving Mr. Witkoff a key role in U.S. relations with Iran, according to a Trump official, which would further enhance his standing, giving him responsibilities on par with a secretary of state.
Mr. Witkoff has already dipped his toe in Iran negotiations, stopping in the United Arab Emirates this week to give a letter from Mr. Trump to a senior Emirati diplomat to pass on to Iran. The letter, addressed to Iran’s supreme leader, offered to negotiate a nuclear deal with Tehran. Mr. Witkoff’s role was reported earlier by Axios and confirmed by a person familiar with the matter.
Mr. Witkoff has no designs on Mr. Rubio’s job, according to someone close to him. Speaking to reporters this week, Mr. Rubio called Mr. Witkoff “a fantastic person” and said they speak regularly.
During his first term, Mr. Trump sent his secretary of state, Mike Pompeo, to Moscow for a meeting with Mr. Putin. Given that Mr. Rubio has a record of denouncing Mr. Putin as a “butcher” and a war criminal, Mr. Witkoff could be a more palatable alternative.
One crucial question is whether Mr. Witkoff is negotiating with Mr. Putin or simply acting as a trusted messenger, said Thomas Graham, who served as the N.S.C.’s top Russia official in the George W. Bush White House.
Even that role brings risks for someone not fluent in U.S.-Russa policy, Mr. Graham said.
And while Mr. Putin may be notorious for his use of confusion and misinformation, in the case of Mr. Trump his initial goal may be clarity.
“The concern is, does Witkoff understand exactly what Putin is telling him and convey that properly?” said Mr. Graham, who recently visited Moscow.
“I can tell you that the Kremlin likes Witkoff because they believe that he does provide a direct channel to Trump,” he added. “But they are concerned that because of this lack of Russia expertise, he doesn’t fully comprehend what he’s being told, and that he might convey to Trump things that are at odds with what the Russian position really is. And that can bring complications in a negotiation.”
Russia experts grimaced in late February, when Mr. Witkoff told reporters that a draft settlement between Russia and Ukraine negotiated during the opening days of Russia’s invasion could serve as a “guidepost” for future negotiations.
Ukrainian officials said the plan was a non-starter. It had been negotiated when it looked like Russia might swiftly overrun their country, they said, and would amount to near-total capitulation. Ukrainian officials believe they are now in a stronger negotiating position.
In Miami last month, Mr. Kushner acknowledged the risks that Mr. Witkoff faces as a diplomatic outsider, including the prospect of embarrassment.
“Knowing — to get on a plane, to go to Russia — who to trust, who not to trust, how do you feel like you’re able to navigate that?” he asked.
The most important thing, Mr. Witkoff replied, was that “I had the support of President Trump, which is a really big deal.”