When President Trump appointed his friend Stephen Witkoff as an envoy in the Middle East last November, the choice encouraged him to hit his head in diplomacy.
Many foreign officials have never heard of Witkoff, a billionaire New York property developer who has known Trump since the mid-1980s. The President's new envoy, apart from some business transactions, not only lacked expertise in the region, but also had no diplomatic experience.
It was not important for the president who took Washington credentials into account for responsibility and viewed foreign policy as a series of business transactions. And Trump was impressed by Witkov's ability to help the outgoing Biden administration seal a temporary ceasefire contract in Gaza between Israel and Hamas.
Now, amid a fresh indication of confidence in his old friends, Trump has expanded Witkoff's portfolio. As Trump pursues the possibility of a peace deal in Ukraine and a restructuring of US-Russia relations, he has made Witkov a personal envoy to Russian President Vladimir V. Putin.
On Thursday morning, Witkov landed in Moscow and met with the Russian leader for the second time in over a month. In mid-February, he and Putin sat for the three and a half hour session that Putin released, where American Mark Vogel, who serves a sentence in Russia for marijuana smuggling charges, was released.
Working with Putin is a mission to make even experienced diplomats take a deep breath. The Russian leader, as an intellectual operative, is a master of blackmail, manipulation and fraud, worthy of the past. Some experts and diplomats who know Putin fear that Witkov might be on top of his head.
Recent indications that Witkov could play a key role in Trump's early diplomacy with Iran against the fast-growing nuclear programme have also raised other questions, such as whether Witkov is at risk of growing too thin. Rubio flew from Doha, Qatar to Moscow, where he helped mediate consultations between Israel and Hamas, extending the fragile ceasefire in Gaza.
In Moscow, Witkov will hear that Putin has taken away Ukrainian ceasefire plans that we and Ukrainian officials agreed to in Saudi Arabia this week. The suspension of combat could be the first step towards Trump's goal of quickly ending the war in Ukraine and normalizing relations with Russia.
The conversation doesn't promise to be simple. Speaking to reporters before Thursday's meeting, Putin raised a series of questions about the plan. Many analysts say there is little incentive to end the war that Putin appears to have the advantage now.
If he agrees to end the war, Putin may argue for key concessions, analysts say.
Witkov is the first senior US official to meet Putin before Russia invaded Ukraine in February 2022. The Biden administration cut off contact with Putin and accused Russia of committing crimes against humanity in Ukraine.
Witkov appears to have been relieved with the Russian leader at the first meeting, saying he spent the “building friendships, relationships” session with Putin at an investment meeting in Miami last month.
The statement contests the idea that Witkov is in line with others and that Russia is a dangerous invader.
Speaking about CNN last month, he said that Russia's invasion of Ukraine was “provoked,” adding, “that doesn't necessarily mean it was caused by the Russians.”
The comment now reflects the view that Putin forced military action as America gradually expanded deeper into Eastern Europe and proposed that Ukraine be its member.
In 2018, Witkov also criticized Western economic sanctions against Russia after annexing Ukraine's Crimea in 2014 and then attempted to influence the 2016 US presidential election. “I never had a frank understanding of Russian sanctions because it was about stopping Russian investments from investing in this country,” he said in an interview with the podcast.
Such stories, along with Witkov's lack of experience with Putin, are concerned about some of the people who know the Russian leader best.
To deal with Putin, “You need to be very well prepared,” said Putin biographer Fiona Hill, who served as Trump's senior national security council director in Russia.
As an example of a counter to Witkoff, Hill recalls CIA director William J. Burns, Messenger President Biden, who was sent to Putin at a moment of crisis in the second half of 2021.
Biden sent Burns to warn Putin that the Ukrainian invasion would cause a serious US response.
“Witkoff clearly hasn't had anyone like Burns ever done,” Hill said. It may be so important, she said, if he is surrounded by experts who can listen to Putin's commentary and provide him with context and fact checks. However, she noted that Witkov, who works with bare bone staff, had not brought anyone to his first meeting with Putin.
Expertise could be a responsibility for Trump, who believes that the playbook creating real estate transactions will be easily applied to international relations.
“I haven't done anything great over the years with Putin's experienced diplomats,” said Richard Haas, president emeritus of the Foreign Relations Council, who should be given the opportunity to prove himself.
A similar idea of ​​the Middle East led Trump to appoint his son-in-law Jared Kushner in his first term.
In an on-stage dialogue led by Kushner along with Witkov at the Miami Investment Conference, Witkov said it was Kushner who persuaded him to join Trump's administration, joking that Kushner had applied a “sidididally smart” tactic to him.
Kushner suggested that Witkoff's real estate records are more valuable at a global stage than traditional foreign policy experience.
“You come from the background of negotiations, transactions and trading, and this is very different from diplomacy,” Kushner said.
Those who worked with Witkoff say he can become a tough, table-striking negotiator. But he has an energetic, hilarious temperament and, as Trump officials have said, the knack for people to “feel like a million dollars.”
Even before Trump's inauguration, Witkoff, who had plunged into difficult negotiations with Israel's Hamas late last year, moved Brett McGurk, who served as Biden's top aide for Middle East affairs and was trying to mediate a ceasefire on Biden's last day.
In an interview, McGurk told Witkoff he found a pragmatist and a “problem solver.” “Whatever Steve is working on is in a capable hand.” McGurk said.
Witkov's role in including negotiations with Moscow – Witkov also joined Rubio and national security adviser Michael Waltz in a meeting with Russian Saudi officials last month.
In November, Trump made retired general Keith Kellogg an envoy for Ukraine and Russia. However, Kellogg appears to be playing a supporting role at the very best now.
Trump is also interested in giving Witkov a key role in US relations with Iran. This further strengthens his position, according to Trump officials, and gives him the same responsibility as the Secretary of State.
Witkov has already dipped his toes in Iranian negotiations and has stopped this week in the UAE, handing a letter from Trump to senior Emirati diplomats to Iran. The letter, addressed to Iran's supreme leader, offered to negotiate a nuclear deal with Tehran. Witkov's role has been reported previously by Axios and confirmed by those familiar with the issue.
According to someone nearby he said Witkov has no designs for Rubio's work. Speaking to reporters this week, Rubio called Witkov a “fantasy person” and said he spoke regularly.
During his first term, Trump sent Secretary of State Mike Pompeo to Moscow for a meeting with Putin. Given that Rubio has a record of criticizing Putin as a “butcher” and a war criminal, Witkov could be a more attractive alternative.
One important question is whether Witkov is negotiating with Putin or simply acting as a reliable messenger.
Even that role poses risks to those who are not fluent in the policies of the US and Lusa, Graham said.
And while Putin may be infamous for his confusion and misinformation use, in the case of Trump, his initial goal may be clear.
“The concern is that Witkov understands exactly what Putin is saying to him and communicates it appropriately,” said Graham, who recently visited Moscow.
“I can say I like Witkov because the Kremlin believes he's providing a channel directly to Trump,” he added. “However, they are concerned that because of this lack of Russian expertise, he doesn't fully understand what is being said and may communicate to Trump that is in conflict with what the Russian position is really, and that can bring complications to negotiations.”
Russian experts told reporters in late February that a draft settlement between Russia and Ukraine could serve as a “guide” for future negotiations during the early days of the Russian invasion.
Ukrainian officials said the plan was a non-star. They said it was negotiated when Russia seemed to overlook their country quickly, and would amount to an almost coincidence of surrender. Ukrainian officials believe they are in a stronger negotiating position than they are now.
In Miami last month, Kushner acknowledged the risks Witkov faces as an outsider of foreign affairs, including a prospect of embarrassment.
“I know – to get on a plane to Russia – who should you trust, whom you don't trust, how do you feel you can navigate it?” he asked.
Most importantly, Witkoff answered: “I was supported by President Trump.
