U.S. President Donald Trump’s special envoy to the Middle East, former real estate lawyer Steve Witkoff, has effectively become the administration’s point man on a wide range of global issues—including sensitive negotiations with Russia and Iran—raising concerns in Washington over his unorthodox diplomatic approach, The New York Post reported this week. Witkoff, described by allies as a “tough negotiator,” has taken on a role that goes far beyond the Middle East, informally serving as Trump’s personal emissary to Russian President Vladimir Putin while simultaneously overseeing U.S. efforts in the Israeli-Hamas ceasefire talks and nuclear negotiations with Iran. 7 View gallery Steve Witkoff ( Photo: KRISTINA KORMILITSYNA / POOL / AFP ) According to the report, Witkoff has participated in high-level meetings in Moscow without the customary team of advisors, military officers or expert staff that typically accompany U.S. officials in such settings.
At times, he has reportedly relied on Kremlin translators—a breach of long-standing diplomatic norms. During his most recent meeting with Putin last Friday, Witkoff greeted the Russian leader with the familiarity of an old friend. No American delegation accompanied him, while Putin was joined by his aide Yuri Ushakov and Kirill Dmitriev, head of Russia’s sovereign wealth fund.
“Anybody engaging in these kinds of talks with Putin would benefit from having experienced Russia hands on his or her team and bringing them along to meetings with the Kremlin,” John Hardie, director of the Russia Program at the Foundation for Defense of Democracies, told the Post. A former senior Trump administration official was more blunt: “Nice guy, but a bumbling f–king idiot. He should not be doing this alone.” Despite the criticism, Witkoff continues to juggle major diplomatic responsibilities.
Alongside his Russia contacts, he is actively mediating between Israel and Hamas in ongoing ceasefire and hostage negotiations, and is engaged in backchannel discussions with Iran over a potential new nuclear deal. Already fooled by Hamas once Witkoff began his tenure on a high note after brokering a major ceasefire agreement between Israel and Hamas. The deal, reached just one day before Trump’s inauguration, resulted in a two-month cessation of hostilities and the release of 33 hostages.
However, Witkoff’s subsequent attempt to extend the ceasefire unraveled quickly. 7 View gallery Witkoff and Donald Trump ( Photo: Reuters ) On March 12, Witkoff left negotiations with Hamas officials in Qatar, believing he had secured a framework for a one-month extension in exchange for the release of five additional hostages in return for a larger group of Palestinian prisoners. But two days later, Hamas countered with a significantly altered proposal: the release of only one American hostage, Edan Alexander , along with the remains of four deceased captives .
Witkoff rejected the offer outright, and the ceasefire collapsed just four days later . “I thought we had a deal,” Witkoff told Fox News a week after the breakdown. “I even believed we had Hamas’ approval.
Maybe I’m the one who feels betrayed. I thought we had reached an agreement—but apparently, we hadn’t.” While many Israelis have praised Witkoff’s efforts, critics have pointed to his lack of diplomatic experience as a liability in high-stakes negotiations. “His assumption that actors like Hamas or Iran are primarily motivated by a desire to live — and can therefore be reasoned with through direct engagement — reflects a dangerous misunderstanding of their long-term ideological goals,” said Shiri Fein-Grossman, former head of regional affairs at the Israel National Security Council.
“We have to understand our enemies through their lens, not ours. Hamas and Iran are autocratic regimes driven by deep-rooted ideologies, not short-term interests.” 7 View gallery Edan Alexander Other experts have expressed concern over the breadth of Witkoff’s responsibilities. “How does Witkoff divide his time with two very demanding negotiations?” asked Danny Citrinowicz, a former Israeli intelligence officer and fellow at the Institute for National Security Studies.
“I think he’s a good guy, but the Iran issue is so complex that I’m hoping he is bringing more people to the team, because as of now, the Iranians might have the upper hand, given their vast knowledge in negotiations.” One envoy for Russia, another for Ukraine When Donald Trump took office on January 20, he already had a special envoy for the Russia-Ukraine war: retired Lt. Gen. Keith Kellogg, a former adviser to Mike Pence who served as Trump’s deputy national security adviser during his first term. However, by mid-March, Kellogg’s title was changed from “Special Envoy for Ukraine and Russia” to “Special Envoy for Ukraine.” Steve Witkoff, meanwhile, was appointed as an ambassador-at-large, tasked with negotiating directly with Russia to end the war—but not with Kyiv, which remained under Kellogg’s purview. Kellogg’s efforts have borne fruit.
He persuaded Ukraine to sign on to a proposed ceasefire agreement and helped shape the minerals deal signed this week between Washington and Kyiv. Still, dividing the negotiation responsibilities between separate envoys for each side appears to be complicating diplomacy. On April 24, Ukrainian President Volodymyr Zelensky said he, Kellogg and a European delegation had reached a mutually acceptable proposal for ending the war during talks in London.
But soon after, Trump announced a new framework that would recognize Russia’s annexation of Crimea—Moscow’s long-standing demand and a red line for Kyiv. 7 View gallery Witkoff meets with Vladimir Putin in the Kremlin ( Photo: Sputnik/Kristina Kormilitsyna/Pool via REUTERS ) “A challenge with the way President Trump split responsibilities between Witkoff and Kellogg,” Hardie said, “is that Witkoff, who is closer to Trump, relays the Kremlin’s view to Trump but has much more limited exposure to Kyiv’s views.” Former U.S. Ambassador to Russia Michael McFaul recently wrote on X that “If Trump finally got serious about mediating an end to the war in Ukraine, he would appoint one person to talk to both sides — shuttle diplomacy — and preferably someone with some experience in diplomacy.” He added, “Witkoff acts as a mailman for Putin.
He is not negotiating anything.” Spreading Russian talking points The controversy surrounding Witkoff deepened after Russian state media picked up on a pattern of Witkoff parroting Vladimir Putin following their meetings. Russian television hosts remarked that Witkoff seemed unusually receptive to Kremlin narratives—at times even more so than the Russians themselves. The most striking example came during a March 21 interview with Tucker Carlson, in which Witkoff reiterated Kremlin talking points, stating that the “most largest issue” in the negotiations was political—specifically, Russia annexing "these so-called four regions,” referring to Donetsk, Kherson, Luhansk and Zaporizhzhia.
Notably, he did not name the Ukrainian regions, which Russia unilaterally annexed at the start of the war. “They’re Russian-speaking,” Witkoff said of the residents of those territories, echoing one of Putin’s long-standing justifications for the invasion. He added that “There have been referendums where the overwhelming majority of the people have indicated that they want to be under Russian rule,” without acknowledging the reports that Moscow had forcibly displaced Ukrainian speakers, suppressed non-Russian language use and conducted those referenda under the watchful eyes of armed Kremlin forces.
7 View gallery Trump and Volodymor Zelensky meeting on the sidelines of Pope Francis' funeral ( Photo: Handout / UKRAINIAN FOREIGN MINISTRY / AFP ) “The Russians are de facto in control of these territories,” Witkoff said in the same interview. “The question is will they be, will the world acknowledge that those are Russian territories? Will Zelensky survive politically if he acknowledges this?
This is the central issue in the conflict. Absolutely.” Ukrainian officials strongly condemned these remarks, with one telling The New York Post, “This is about sovereignty and dignity, not politics.” Zelensky told reporters on April 17 that he believes “I believe Mr. Witkoff has adopted the strategy of the Russian side.” Whether knowingly or not, he said, “he is spreading Russian narratives. Either way, it does not help.” Witkoff has also been criticized for failing to vet or select his own interpreters during negotiations with Putin.
In footage from their most recent meeting, he is heard asking whether the only person seated near him at the table was “from the embassy.” “It is IMPOSSIBLE to have negotiations when you do not trust the translator,” wrote Jaanika Merilo, a Ukrainian-Estonian translator and advisor to the Kyiv government, on X. “Witkoff does not speak Russian, and he cannot verify what is being translated. It is crucial that every nuance is translated correctly and in the context.” “No politician goes to negotiations to hostile environment, what Russia is supposed to be, without his own translator.
You do, if you really trust the other party. Or unless you are not competent. Unless you don’t care.
Beats me but something is off.” 'We cannot just ‘tap along’ with the Iranians' Negotiations over a new nuclear agreement with Iran are, at least theoretically, the easiest item on Witkoff’s packed foreign policy agenda. According to veteran Middle East analysts, the regime in Tehran is at its weakest point in decades—reeling from the Israel-Hamas war, Hezbollah’s waning strength, the fall of the Assad regime and widespread domestic dissent. 7 View gallery Ali Khamenei The U.S. State Department has maintained that Iran must fully dismantle its nuclear and uranium enrichment programs.
However, Iran has thus far firmly rejected those demands and refuses to halt uranium enrichment or shutter its nuclear facilities. After a first round of talks in Oman last month, Witkoff reportedly proposed allowing Iran to keep its facilities if it agreed to maintain uranium enrichment levels well below weapons-grade—similar to the terms of the 2015 nuclear deal negotiated by former President Barack Obama, which Trump later withdrew from during his first term. “You do not need to run, as they claim, a ‘civil nuclear program’ where you’re enriching past 3.67%,” Witkoff told Fox News host Sean Hannity on April 14, “so this is going to be much about verification on the enrichment program.” Get the Ynetnews app on your smartphone: Google Play : https://bit.ly/4eJ37pE | Apple App Store : https://bit.ly/3ZL7iNv However, he walked back those comments the next day, saying, “Any final arrangement must set a framework for peace, stability, and prosperity in the Middle East — meaning that Iran must stop and eliminate its nuclear enrichment and weaponization program.” Andrea Stricker, a researcher at the Foundation for Defense of Democracies (FDD), warned that one of the worst outcomes would be a vague or temporary freeze.
“On a technical level, Iran may say that it’s permanent, but in effect, it would retain all its enrichment infrastructure to wait out the Trump administration and bust out of the restrictions,” she said. “They really need to be put in a position of seeing the nuclear program as a threat to their survival, rather than something that protects their survival.” 7 View gallery John Bolton ( Photo: AFP ) Trump’s former national security adviser John Bolton was more blunt, calling Witkoff’s talks with Iran “a waste of oxygen.” On X, he wrote, “The Iranians are trying to buy time and relief from economic sanctions so they can rebuild their military. We cannot just ‘tap along’ with the Iranians.
Trump is making the same mistakes Obama did in 2015.” Behnam Ben Taleblu, also of the FDD, said Tehran is likely to stretch out the negotiations if Witkoff and Trump allow it. According to him, the Iranians believe that “so long as Washington is talking, Jerusalem is not shooting — and through that prism everything else flows.” “The foremost element of Tehran’s diplomatic strategy today is not to earn sanctions relief …,” he added. “The foremost strategy is to use direct engagement with the United States as a literal human shield against an Israeli preemptive attack against Iran’s nuclear and/or military installations.” Sources familiar with the talks said Israel is preparing to strike Iran’s nuclear facilities and may do so even without U.S. military backing.
In response to the New York Post report, White House deputy press secretary Anna Kelly said: “It is a badge of honor to be the target of a John Bolton tantrum. He and his fellow warmongers quoted in this so-called ‘news piece’ thrive off forever war — lining their pockets while young people die. “Steve Witkoff has done incredible work securing the release of Americans detained abroad, like Marc Fogel, while leaving behind a massive business enterprise to serve his country.
Like President Trump, he is focused on stopping the killing and advancing peace through strength.”
