How Trump friend Steve Witkoff ended up at the center of high-stakes Ukraine, Israel negotiations

(CNN) — When Donald Trump was convicted on 34 felony counts by a jury last May, there was one person in his courtroom entourage who wasn’t one of his lawyers, aides or family members: Steve Witkoff.

While a parade of Trump allies came in and out of the Manhattan courtroom throughout last year’s seven-week trial — including Trump’s eventual vice president, JD Vance — it was Witkoff who stayed by Trump’s side during the final hours after two days of jury deliberations, a sign of the close friendship between the two real estate moguls.

Now that longtime friendship with Trump has thrust Witkoff in the middle of two of the biggest foreign policy crises facing Trump’s second term. Named Trump’s Middle East envoy shortly after the president won a return to the White House in November, Witkoff worked with Biden administration’s officials to finalize a ceasefire deal between Israel and Hamas.

His portfolio has now expanded to the Russia-Ukraine war, and Witkoff accompanied Secretary of State Marco Rubio and Mike Waltz, Trump’s national security adviser, for a meeting with Russian Foreign Minister Sergei Lavrov in Saudi Arabia on Tuesday that served to jumpstart US-Russian relations.

While Witkoff has never served before as a diplomat or even worked in government, Trump views him as the ultimate dealmaker.

“Outside of family, there is no one as trusted by DJT as Steve,” a White House official told CNN.

‘A politer version of Trump’

During Trump’s 2024 presidential campaign, Witkoff served as Trump’s de facto personal diplomat, facilitating talks with several of Trump’s top Republican rivals. In the first month of Trump’s second term, Witkoff has traveled the globe on Trump’s behalf — often in his own private jet. He met with world leaders — including Russian President Vladimir Putin — helped secure a prisoner swap with Russia and was the first US government official to visit Gaza in years.

People who have attended meetings with Witkoff describe him as good-natured but to-the-point — “a politer version of Trump,” one person said, with a sense of how to wield leverage in ways that can ease some certain tense negotiations.

Sources close to Trump say the president has long believed he forged his negotiating skills through his real estate career. Trump sees the same qualities in Witkoff, viewing the two as being cut from the same cloth. That shared experience is something virtually no one else in the Trump administration possesses.

Witkoff also has a leg up over other high-ranking Trump officials in that he knows how Trump operates. And his long friendship with Trump gives Witkoff the benefit of longevity to keep his seat at the negotiating table even as Cabinet secretaries and other top Trump officials may come and go, like they did in Trump’s first term.

While Witkoff was in the room Tuesday alongside the secretary of state and national security adviser, Trump’s Russia-Ukraine envoy, Keith Kellogg, was notably absent. Sources who have spoken to Kellogg about the situation believe that he has been sidelined from any discussions with Moscow because of his more hawkish views on Russia, including pushing for continued US military aid to Ukraine and security guarantees to help Kyiv negotiate from a position of strength.

Two sources said the Russians have indicated they would rather negotiate with Witkoff than Kellogg.

The White House pushed back on that assertion, with one official telling CNN that Kellogg has instead been tasked by Trump to focus on negotiations with Ukraine and the United States’ European allies. Kellogg is in Kyiv this week meeting with Ukrainian President Volodymyr Zelensky.

The learning curve will be steep in trying to bring an end to the three-year Russia-Ukraine war, veteran foreign policy hands say, with a negotiation that threatens to upend the US role in the world and the US-European relationship amid fears Trump is cozying up to Putin.

“Whether or not Witkoff is going to be the main guy in a Russia-Ukraine negotiation, it’s a different sort of lift from the one he’s currently involved in in the Middle East.” said Aaron David Miller, a seasoned Middle East negotiator who worked for multiple US administrations.

“He’s yet to be tested on this,” added Miller, a senior fellow at the Carnegie Endowment for International Peace. “When it comes to Russia and Ukraine, it’s not like developing a piece of property or a shopping center. This is politically existential — and for Zelensky it’s even more than just politically existential.”

Meeting at a New York deli

The road to Witkoff’s role negotiating some of the world’s biggest diplomatic crises began with a ham and Swiss sandwich at 3 in the morning.

Witkoff has described in court how he and Trump first met at a New York delicatessen early one morning around 1986 when he was a lawyer. Witkoff testified on Trump’s behalf in November 2023 during at Trump’s civil fraud trial, where the New York attorney general was seeking hundreds of millions of dollars alleging Trump and his company inflated the value of his assets to obtain more favorable loan and insurance rates.

“He didn’t have any money with him, and I was ordering from a local delicatessen for the people who were on my team,” Witkoff said. “And he asked me if I would order him a ham and Swiss sandwich.  So that was the first time I met him.”

Years later, Witkoff said, he saw Trump again at a restaurant. “He actually remembered who I was and remembered the sandwich incident. And had just developed a friendship as a result of it,” Witkoff said while on the stand.

Trump and Witkoff, who transitioned his law career into running a lucrative New York real estate company, remained friends over the past two decades. They stayed close throughout Trump’s political rise in 2016, his brief political exile in 2021 and his triumphant return last year.

Witkoff’s son Zach got married at Mar-a-Lago in 2022. Unlike many Mar-a-Lago weddings that feature a quick drop-in by Trump, at this event the former (and future) president stayed well into the evening with his wife, Melania.

During Trump’s 2024 campaign, Witkoff was already acting as an unofficial envoy to Trump’s rivals for the GOP nomination. Witkoff arranged a meeting between Trump and Florida Gov. Ron DeSantis in April 2024. And Nikki Haley described on her radio show how Witkoff came to her house in South Carolina to ask what she wanted for a truce with Trump.

The real estate mogul was also crucial to helping get Trump elected. Not only did he donate millions of dollars to Trump’s campaign and outside political organizations, but he also helped facilitate meetings and fundraisers with other wealthy donors who helped fuel Trump’s victory.

Witkoff was on the links with Trump in in September when a would-be assassin hid in the bushes outside Trump’s Florida golf course, the second assassination attempt on Trump’s life last year.

“All of a sudden we heard shots being fired in the air, and I guess probably four or five, and it sounded like bullets,” Trump later said of the incident. “But what do I know about that? But Secret Service knew immediately it was bullets, and they grabbed me, and I think probably the other one, Steve is one of the people. Steve Witkoff, a great friend of mine.”

A rare partnership

Witkoff didn’t serve a formal role in Trump’s first administration. But a week after Trump won back the White House in November, he named Witkoff as special envoy to the Middle East.

As a Jewish real estate magnate, and a businessman with international financial dealings, Witkoff already had existing relationships with Israelis, something people close to Trump described as the reasoning behind why he was initially tapped for the role.

At the start of this year, Witkoff found himself at the center of perhaps the only area of cooperation between the incoming and outgoing administrations: brokering a ceasefire deal in Gaza that, for months, had eluded President Joe Biden and his team.

His presence in Doha during the final days of the talks — and earlier in Israel, when he sat for a rare Saturday meeting with Prime Minister Benjamin Netanyahu — was met with some initial skepticism by some of Biden’s aides in Washington, who predicted it would allow Trump to take credit for a deal (in that, they were correct).

Yet it quickly became clear to Biden’s own negotiating team that Witkoff was as serious-minded and helpful in the talks as any seasoned diplomat, even amid eleventh-hour setbacks. Working into the early morning hours to finalize text of the agreement, Witkoff sometimes arrived to negotiating sessions in sneakers and sweatpants.

One senior Biden official described the partnership between Witkoff and Brett McGurk, his counterpart in the Biden administration, as “historically almost unprecedented” and “a highly constructive, very fruitful partnership.”

“Steve and I developed a very close partnership, even friendship, and at the time to close the deal, I was very grateful that Steve came out to Doha in these last few days,” McGurk told CNN last month.

Another person familiar with the discussions in Israel and Qatar said while Biden’s team was there to manage the specifics of the arrangement, Witkoff acted as a reminder that Trump wanted the deal completed before he entered office.

Later, Israeli officials said Witkoff — and, by extension, Trump himself — were the deciding factor that put the deal over the finish line.

After the ceasefire took effect and hostages began being released from Gaza, Witkoff returned to Israel, meeting with Netanyahu about the next phase of the agreement ahead of Netanyahu’s White House meeting with Trump.

Witkoff also traveled to Gaza, the first US official to do so in years. When he returned to Washington, Witkoff gave Trump a dire impression of the devastation he witnessed. He told reporters that he viewed it as being no longer habitable.

Witkoff’s descriptions were an “inflection point” for Trump, a White House official told CNN, and the president subsequently proposed removing Palestinians from Gaza so it could be rebuilt — a plan sharply rebuked by Arab leaders.

Witkoff was dispatched to Capitol Hill to field questions behind closed doors from Republican senators concerned about Trump’s Gaza plans, and he defended Trump’s ideas publicly.

“When the president talks about cleaning it out, he talks about making it habitable. And this is a long-range plan,” Witkoff told reporters at the White House earlier this month.

Trump asks, ‘and we say yes’

Witkoff’s next assignment took him out of the Middle East and into the US government’s highly adversarial relationship with Russia.

“Witkoff proved early on that he had the chops to be a dealmaker. He helped reach a breakthrough where others couldn’t. That success led the president to give him more jobs,” a Trump administration official said.

Witkoff was sent to Russia to try to negotiate the release of Marc Fogel, an American teacher who had been wrongfully detained for three years.  When he arrived on the ground in Russia, a deal wasn’t yet in place. “There was still work to do,” Witkoff would say later.

While in Moscow, Witkoff met directly with Putin, as well as Kirill Dmitriev, a close Putin adviser who played a significant role in the Fogel talks, Witkoff said. The Middle East envoy also credited the role that Saudi Crown Prince Saudi Crown Prince Mohammed bin Salman played in the talks as “instrumental.”

Witkoff was on the ground for six or seven hours in Russia, and he left Russian airspace with Fogel on his plane, returning the American prisoner to the US.

Upon his return, Witkoff repeatedly gave Trump credit for the deal and thanked the president for empowering him to be the conduit — a sign of Witkoff’s experience in dealing with Trump.

“In general, with President Trump, he asks, and we say yes,” Witkoff told CNN the day after Fogel’s release.

The next day, Trump spoke with Putin by phone, setting the stage for Tuesday’s talks between the US and Russian delegations. The move angered Zelensky and America’s allies in Europe, who felt they were being shut out and feared what Trump would agree to.

While Witkoff and other top Trump officials traveled to Saudi Arabia for talks with the Russian delegation, Kellogg was dispatched to Kyiv Wednesday, where he is expected to meet with Zelensky. Rather than engaging in negotiations, Kellogg will undoubtedly be left to deal with any fallout from the US-Russia meeting and Trump’s recent public attacks on the Ukrainian president.

At the conclusion of Tuesday’s meeting with Lavrov, Witkoff had nothing but good things to say about the discussion. “It was positive, upbeat, and constructive, everybody there to get to the right outcome. Solution-based. We discussed it afterwards. We couldn’t have imagined a better result after this. It was very, very solid,” he told reporters.

What happened next underscored the challenge ahead for Witkoff and the US team preparing to negotiate with Russia: Trump attacked Zelensky and falsely blamed Ukraine for starting the war with Russia.

“I think I have the power to end this war, and I think it’s going well. But today I heard, ‘Oh well, we weren’t invited,’” Trump told reporters Tuesday afternoon at Mar-a-Lago. “Well, you’ve been there for three years. You should’ve ended it after three years. You should’ve never started it. You could’ve made a deal.”

CNN’s Zachary Cohen, Natasha Bertrand and Jennifer Hansler contributed to this report.

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