Just weeks removed from playing a critical role in the Israel-Hamas ceasefire, President Donald Trump's Middle East envoy, Steve Witkoff, now appears to have a major role in the administration's efforts to end Russia's war in Ukraine.
Witkoff, who had no diplomatic experience prior to Trump's victory last November, was one of three senior administration officials who met with senior Russian leaders in Saudi Arabia on Tuesday. Witkoff, Secretary of State Marco Rubio, and national security adviser Mike Waltz led the U.S. delegation.
Witkoff's involvement in the administration's efforts to smooth relations between Moscow and Washington was largely unknown until last week when he personally traveled to Russia to bring home a wrongfully detained American named Marc Fogel. Fogel had been arrested on drug charges and had spent three and a half years in a Russian prison on the charges, while the United States agreed to free a Russian crypto-scammer, Alexander Vinnik, in exchange.
He was the first U.S. official to touch down in Moscow since Russia's war in Ukraine began in February 2022.
Trump’s Russia-Ukraine envoy, Gen. Keith Kellogg, did not travel to Riyadh for the meeting with Russian Foreign Minister Sergei Lavrov and Vladimir Putin's foreign policy adviser Yuri Ushakov, though he is set to travel to Ukraine later this week.
"He may be the greatest guy ever, but these are hugely consequential issues that he's not spent very much time [on] previously," Danielle Pletka, a senior fellow with the American Enterprise Institute told the Washington Examiner. "You have to ask yourself whether you are giving your guy the maximum possible advantage to do the best job possible. And that's already a tall order when it comes to the challenge of Hamas, when it comes to the challenge of Russia and Ukraine as well, now, I wouldn't want to be Steve Witkoff's cardiologist."
Witkoff, a 67-year-old real estate developer praised for his direct style, also played an integral role in securing the Israel-Hamas ceasefire as well as ensuring the Israel-Hezbollah ceasefire held firm, which was agreed upon prior to Trump's return to power.
"The president sees Steve as one of the world's great deal-makers," a White House official told Axios. "Game respects game."
Witkoff's entry into the Israel-Hamas negotiations provided a much-needed spark for the deal to get over the finish line, while his participation in the deliberations gave assurances to all parties that the incoming administration would uphold a deal.
Pletka called Witkoff and Kellogg's involvement "very Trumpian" in that Trump effectively decided, "I like this guy, so never mind that I named that guy to be the negotiator." Pletka also compared it to the famous Abbott and Costello "Who's on first?" skit.
Since the ceasefire took effect last month, Witkoff became the first U.S. official in years to travel to Gaza.
"There is nothing left standing. Many unexploded ordnances. It is not safe to walk there. It is very dangerous. I wouldn't have known this without going there and inspecting," he said of Gaza. "There has been this perception we can get to a solid plan for Gaza in five years. But it's impossible. This is a 10 to 15-year rebuilding plan."
He also called Gaza "uninhabitable," which has been a frequent refrain from the administration.
The president unveiled a plan to relocate Palestinians to nearby Arab nations while the U.S. leads a reconstruction effort. Trump has viewed the project as a real estate venture, dubbing the end goal the "Riviera of the Middle East," while critics, including the leaders of nearly every Arab-majority nation, have denounced the plan and accused the administration of pursuing the ethnic cleansing and forced displacement of the Palestinians.
Trump has said Palestinians would not have the right to return home after leaving for a neighboring country.
Pletka said Trump has had "revolutionary ideas" for the Middle East, "but there are practical aspects to them that are going to be complex for the president's negotiators to figure out."
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Israel and Hamas are set to begin negotiations for Phase II of the ceasefire deal, though the conversations are already behind schedule compared to the timeline laid out at the onset of the deal. The two sides have agreed to a framework, though getting both sides to agree on the details will be difficult for the U.S., Qatar, and Egypt, which have acted as mediators.
Israeli leaders have said they will not agree to end the war indefinitely if it means leaving Hamas in power. The framework for Phase II includes Israel withdrawing all its forces from Gaza in exchange for the release of all remaining living hostages Hamas has held since the Oct. 7, 2023, terrorist attack.
Trump's effort to take over the enclave could pose an additional hurdle in the negotiations.