On April 11, U.S. President Donald Trump's special envoy Steve Witkoff made a surprise visit to St. Petersburg, where he met with Russian President Vladimir Putin, on his way to Oman.Gavriil Grigorov/Reuters
After years of hostilities, the United States and Iran are set to return to the negotiating table Saturday for talks aimed at convincing Tehran to give up its nuclear program.
The Iranian delegation at the meeting, which will be hosted by the Gulf state of Oman, will be predictably headed by Foreign Affairs Minister Abbas Araghchi. But it will not be Secretary of State Marco Rubio sitting across the table from him. The U.S. side will instead be led by Steve Witkoff, a New York real estate developer and golfing buddy of U.S. President Donald Trump. Over the past five months, Mr. Witkoff has gone from having no diplomatic experience at all to being simultaneously tasked with ending the wars in Gaza and Ukraine and, now, defusing the threat of a nuclear Iran as well.
No U.S. diplomat since Henry Kissinger has been given such sway over the country’s foreign policy – and Mr. Kissinger was a renowned expert on nuclear issues and foreign policy before he was appointed Richard Nixon’s secretary of state in 1973.
Mr. Witkoff’s track record so far is mixed. While he can claim a few successes, the wars in Gaza and Ukraine rage on.
These conflicts, among the most intractable, may simply be too much for any one person to handle. Mr. Witkoff – who has already been criticized for not having a firm grasp of the intricacies of the Russia-Ukraine war – is now heading into what will likely be extremely technical negotiations regarding Iran’s nuclear program. The two sides can be expected to wrangle over details such as allowable levels of uranium enrichment and the number of gas centrifuges Tehran might be permitted to keep.
“The guy’s a real estate developer. He may be a seasoned business negotiator, and that has value, but he’s not a diplomat with this kind of international experience. He’s got a hell of a lot on his plate and he’s still staffing up,” said James Dorsey, an honorary fellow in the Middle East Institute at the National University of Singapore. “You could argue that – given all of that – he hasn’t done that badly.”
Mr. Witkoff’s direct line to the President of the United States may prove to be more important than any diplomatic experience or lack thereof.
He appears to have Mr. Trump’s complete trust. In Mr. Witkoff’s own telling, that closeness dates back to 1986, when he and Mr. Trump were working on a real estate transaction together. The two men went to a deli in New York, and Mr. Trump revealed that he hadn’t brought any money with him. “I ordered him a ham and Swiss,” Mr. Witkoff told a Manhattan civil court judge in November, 2023, when Mr. Trump was facing fraud accusations.
Mr. Witkoff (left) has gone from having no diplomatic experience at all to being tasked with ending the wars in Gaza, Ukraine and, now, defusing the threat of a nuclear Iran.JIM WATSON/AFP/Getty Images
He testified that Mr. Trump remembered “the sandwich incident” when the two men met again years later and eventually became friends. Mr. Witkoff has donated millions of dollars to Mr. Trump’s political campaigns and advised him on tax issues during his first stint in the White House. Mr. Trump frequently refers to him as “my pal” or “a special guy.”
The biggest win Mr. Witkoff has achieved so far is the Jan. 15 ceasefire between Israel and Hamas, agreed to five days before Mr. Trump was sworn in. It led to a break in the fighting and the release of 33 of the hostages Hamas had been holding since its Oct. 7, 2023, attack on Israel, as well as nearly 1,800 Palestinians being held in Israeli prisons. But that deal collapsed March 18, with Israel resuming its full-scale assault on Gaza.
Mr. Dorsey said Mr. Witkoff has since “toed the Israeli line” by blaming Hamas alone for the collapse of the ceasefire, even as tens of thousands of Israelis have taken to the streets to protest Prime Minister Benjamin Netanyahu’s decision to resume the war.
Mr. Witkoff also helped broker what was supposed to be a limited ceasefire between Russia and Ukraine. But while the March 25 deal was supposed to see an end to fighting in the Black Sea and a halt in attacks on energy infrastructure, the war has continued unabated after Russia said its agreement to the deal was contingent on the U.S. lifting key sanctions against its agricultural and banking sectors. That hasn’t happened so far.
Many Ukrainians are bitterly critical of Mr. Witkoff’s negotiating style, which has seen the 68-year-old envoy shuttle between Moscow and Kyiv while largely seeking concessions only from the Ukrainian side. He has become a figure of derision in Kyiv after he was unable, in an interview last month with far-right podcaster Tucker Carlson, to name the five regions Russia claims to have annexed from Ukraine.
He suggested in the same interview that the Kremlin had a legitimate claim to the Ukrainian regions of Crimea, Donetsk, Luhansk, Zaporizhzhia and Kherson because they had held “referendums where the overwhelming majority of the people have indicated that they want to be under Russian rule.” The votes were carried out under military occupation and were previously recognized only by Belarus, North Korea, Syria and Nicaragua.
Afterward, Ukrainian President Volodymyr Zelensky criticized Mr. Witkoff for “quoting Kremlin narratives.” Russian President Vladimir Putin, meanwhile, has matched Mr. Trump by leaving the professional diplomats at home and naming Kirill Dmitriev – a businessman and friend of Mr. Putin’s – as his personal envoy.
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Last week, the U.S. quietly lifted travel restrictions the Biden administration had placed on Mr. Dmitriev, who heads Russia’s largest sovereign wealth fund, so he could travel to Washington for talks. Many Ukrainians are worried about the direction the peace process is heading in under Mr. Witkoff’s direction.
“I do not see [Mr. Witkoff] as having strong grasp on the issues. He is also incapable of coming to his own conclusions, it seems. Only translating messages from Moscow, uncritically, to the President,” said Volodymyr Dubovyk, an associate professor of international relations at Mechnikov National University in the Ukrainian port city of Odesa.
On Friday, Mr. Witkoff made a surprise visit to St. Petersburg, where he met with Mr. Putin, on his way to Oman. Afterward, Kremlin-controlled media reported that a follow-up phone call between Mr. Putin and Mr. Trump was “theoretically possible.”
The Iranians are wary as they enter Saturday’s talks – it was Mr. Trump, after all, who in 2019 tore up a deal negotiated by the Obama administration that had seen Tehran agree to curbs on its nuclear program in exchange for a lifting of some sanctions.
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In a letter to Iran’s Supreme Leader, Ayatollah Ali Khamenei, Mr. Trump gave the talks a two-month deadline. If a deal isn’t reached, he has threatened to attack Iran or allow Israel to attack it. In response, Ali Shamkhani, an adviser to Ayatollah Khamenei, said Iran would expel inspectors from the International Atomic Energy Agency if such threats continued.
The ground is nonetheless seen as fertile for some kind of deal. Iran’s network of allied militias around the Middle East has been badly damaged by Israel’s wars against Hamas in Gaza and Hezbollah in Lebanon, as well as the U.S. air strikes against the Houthi rebels in Yemen, leaving Tehran in need of an agreement that prevents all-out war with the U.S., Israel or both. Iranian President Masoud Pezeshkian was elected last year with a mandate to negotiate an end to the U.S.-led sanctions that have battered the Iranian economy.
Mr. Trump, meanwhile, promised on the campaign trail that he would end the world’s wars. The question is whether his “special guy” can deliver a deal with Iran that lasts longer than the ceasefires he negotiated in Gaza and Ukraine.