As the world waits for Russia’s next move over the US-proposed ceasefire deal with Ukraine, only one man has been trusted to head up Donald Trump’s envoy to Moscow – and he’s far from the typical diplomat.
Initially named as Mr Trump’s Middle East envoy shortly after the US election, Steve Witkoff has since been involved in negotiations with Russia about ending the war in Ukraine.
His surprise trip to Moscow last month to achieve the release of US citizen Marc Fogel seemed to secure the 67-year-old as the US leader’s geopolitical dealmaker-in-chief.
Off the back of his first meeting with Russian President Vladimir Putin, Mr Witkoff is believed to be seeing him again later this week to discuss diplomatic proposals – though the Kremlin is yet to confirm this.
He has been chosen to go to Moscow by Mr Trump over US secretary of state Marco Rubio, who on paper is the country’s top diplomat, and Keith Kellogg, who was assigned to be the US envoy for Russia-Ukraine peace talks back in January.
So who is Steve Witkoff, and how important a figure will he be as the US tries to navigate peace between Russia and Ukraine?
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‘Trump is listening intently’ to European leaders
From New York real estate to the Oval Office
Born in the Bronx, New York State, Mr Witkoff trained as a lawyer in real estate before turning his hand to property development.
In the 1990s he created his company, the Witkoff Group, which owns a number of properties in New York, most notably the Park Lane Hotel and The Woolworth Building.
Similarly to Mr Trump, he brought his close family members into his company, including his wife, Lauren Rappoport, and their sons Zach and Alexander, who is co-chief executive.
As of 2019, the Witkoff Group owned almost 50 properties across the US and the rest of the world.
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‘If Russia says no, it will tell us a lot’
‘My dear friend President Trump’
The billionaire has known Mr Trump for decades, having first met him through a New York real estate company where the now president was a client.
Having remained close, the pair bonded over their mutual love of golf, and weredescribed by US senator Lindsey Graham as “longtime golf buddies”.
Mr Witkoff was one of those on the fifth hole with the president at his course in West Palm Beach, Florida, in September last year, when a second apparent assassination attempt was made on his life.
Image: Mr Trump and Mr Witkoff back in 2018. Pic: AP
But despite being regular opponents on the course, Mr Witkoff and Mr Trump are very much aligned in politics, with the businessman having donated to the Republican Party during the 2024 election.
He even spoke at the Republican National Convention back in July last year, where he said he had the “privilege” of calling Mr Trump a “true and dear friend for many years, in good times and bad times”.
Mr Witkoff also firmly backed Mr Trump’s foreign policy, saying at the inauguration parade: “We are done carrying the financial burden of nations that are unwilling to fund their own progress.
“The days of blank checks are over”.
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During Mr Trump’s first term in office, Mr Witkoff played a more minor role, serving as one of the president’s Great American Economic Revival Industry Groups – which aimed to combat the effects of the COVID-19 pandemic.
It was over lunch with Mr Trump after his second election win that Mr Witkoff reportedly broached the idea of working on the Middle East – a region he has extensive business ties with, according to NBC.
“That stunned me because I didn’t know he was that interested in the Middle East,” Senator Graham told NBC back in January, while discussing Mr Witkoff’s appointment.
“And Trump looked at me and said: ‘Well, a million people have tried. Let’s pick a nice guy who’s a smart guy’.”
Image: Mr Trump and Mr Witkoff speaking in January. Pic: AP
Since the beginning of the year, Mr Witkoff has proven to be a critical player in negotiations between Israel and Hamas – helping to secure January’s ceasefire deal which has so far seen the release of some of the remaining Israeli hostages in exchange for Palestinian prisoners.
One person familiar with the negotiations described Mr Witkoff to NBC as someone who is “very much engaged” with “his heart is in the right place”.
A Middle Eastern diplomat, who spoke with NBC on condition of anonymity at the time, added that the businessman was a tough negotiator but was also able to “empathise” with parents who have lost their children on both sides of the conflict, as he openly spoke about his son Andrew, who died of an OxyContin overdose in 2011 aged 22.
Image: US delegation – featuring Mr Witkoff – meets with Saudi and Russian officials. Pic: Reuters
Growing criticism
Despite praise for Mr Witkoff’s approach to geopolitics, there is also growing criticism against him.
Shortly after his visit to Gaza back in January, he backed Mr Trump’s surprise announcement that the US wanted to “develop” the region and turn it into the “Riviera of the Middle East”.
Mr Trump suggested that Gaza’s two million people would not return to their territory under the plans, which has been widely criticised as amounting to ethnic cleansing.
Image: Mr Witkoff said he had developed a ‘friendship’ with Vladimir Putin
Mr Witkoff also faces questions over his first private meeting with President Putin last month, in which he said he had developed a “friendship”with the Russian leader.
Speaking about his relationship with Mr Putin, he said: “I spent a lot of time with Putin. Talking and developing a friendship and relationship with him…”
He claimed their conversation lasted over three hours.
However, the details of the conversation and what was discussed have never been released, with only translators present at the time.
Donald Trump’s eldest son has said his father may walk away from the Ukraine peace process, claiming the issue is not a priority for Americans, and signalling Europe needs a better plan.
In a wide-ranging discussion with Sky’s lead world news presenter Yalda Hakim at Doha Forum 2025, Donald Trump Jr addressed issues including the US administration’s recent diplomatic efforts around the world.
He was speaking in his capacity as a business leader, setting out his agenda for “America first” investments in defence technology and artificial intelligence (AI), drawing a direct line between global stability and economic prosperity.
Image: Donald Trump meeting Volodymyr Zelenskyy in Washington earlier this year. Pic: Reuters
When asked directly if he believed the US president would walk away from Ukraine, he answered: “I think he may, what’s good about my father and what’s unique about my father is you don’t know what he’s going to do. He’s unpredictable.”
President Trump has led renewed efforts for a ceasefire deal with Russia in recent months.
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Drawing a parallel with his father’s current “war” on drug cartels, Donald Trump Jr described gangs bringing illegal drugs into America as a “far greater clear and present danger to the US than anything [going on] in the Ukraine or Russia”.
While he said he did not believe Ukraine would be “abandoned”, he said: “The American public doesn’t have the appetite [for endless wars and further funding of Ukraine’s military efforts].”
Describing Ukraine as “a far more corrupt country than Russia”, he characterised Ukrainian President Zelenskyy as “one of the great marketeers of all time”, who he said had become “a borderline deity, especially to the left”.
He went on to describe President Trump’s approach as “common sense”.
China rivalry was the focus, but Musk got a mention
In a country and at a conference which is friendly, even admiring of the Trump administration, Don Jr was in his element.
He’s here in his capacity as a business leader, promoting his venture, 1789 Capital which claims to be focused on “America First” investments.
But he wasn’t shy about discussing his father’s foreign policy achievements, boasting that Donald Trump had resolved seven or eight wars – conflicts that most ordinary Americans were unaware of.
His pitch is bullish and direct – the current US administration is projecting strength globally, stopping wars and creating investment opportunities which serves the American economy. It’s the MAGA mentality for the global audience.
It’s clear that the rivalry with China is their biggest focus, especially finding ways to combat their dominance over critical minerals.
“America can no longer just sit there and hope that China is going to be a good actor… I think the rest of the world understands that they want America to be at the forefront of all of that.”
When I asked him about recent efforts by President Trump to bring the war in Ukraine to an end, he responded forcefully. “We want peace, we want to stop the death.”
But he went on to say that Europe needed to shoulder the burden and currently they have no plan.
As he sat on the stage in Qatar, the country which has been at the centre of the ceasefire efforts for Gaza, he expressed hope that peace would prevail, but balanced expectations America would fund its re-construction. This would have to be a global effort.
“If there’s one thing my father is, it’s a builder… I think he can be the greatest construction manager in the history of the world, but no one in America wants to bear the entire responsibility of that.”
And, away from international diplomatic efforts, he was happy to announce a breakthrough closer to home.
The “bromance” with Elon Musk and President Trump is back on – calling the entrepreneur a “generational talent, a generational level of genius”.
‘Bromance’ back on
He also confirmed that Tesla billionaire Elon Musk was “100% back in the fold”, after previously appearing to fall out with the president.
Earlier this year, Donald Trump Jr’s investment company, 1789 Capital, heavily invested in some of Musk’s companies, including SpaceX.
Image: Elon Musk and Donald Trump in the Oval Office at the White House in May. Pic: AP
Directly comparing President Trump with Musk, he said: “Imagine dealing with one Donald Trump – now I have to deal with two.
“They’re very similar that way, so it created some headaches… but the reality is they’re both very much aligned, they’re on message with what we want to do with our country. What we want to do with freedom of speech.”
He went on: “Elon did incredible things for Twitter, really allowed the democratisation of truth and freedom and free speech to occur. That’s something that is a true threat in America right now.”
He also praised Musk as “changing the face of free speech, science and technology”, adding, “we have to protect our geniuses”.
When asked whether Mr Trump would stand for a third term, he joked that he could be “just trolling” those on the left.
He went on, “He’s the most unpredictable person, probably in the history of politics. Which is why he’s able to get something done. We’ll see.”
A hidden, underground military base in eastern Ukraine is so secret, soldiers change into civilian clothes whenever they step outside to avoid drawing attention.
Journalists are not usually allowed access.
But the unit that has been using this vast, subterranean warren of war rooms, a dormitory, kitchen, canteen and makeshift gym as its headquarters since the summer is imminently relocating, so Sky News was invited inside.
Lieutenant Colonel Arsen Dimitric – call sign Lemko – is the chief of staff of 1st Corps Azov of the National Guard of Ukraine, one of the country’s most effective combat forces.
Image: Lemko
He sat with us in the base, next to a large square table, covered by a map of the Donbas region.
His soldiers have been fighting in this area since the summer, countering a surge in Russian attacks in and around the frontline city of Pokrovsk.
“We aim to destroy as much of the enemy as possible,” he said.
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“Will we take losses? Yes. Will it hurt? Absolutely.”
But he said if Russia is allowed to advance, even more Ukrainians will suffer.
“Their [the Russians’] only advantage is numbers,” he said.
“They don’t care how many people they lose.”
Lemko said almost 17,000 Russian soldiers had been killed or wounded fighting in this section of the warzone alone between August to November.
Ukrainian video footage of the battlefield showed Russian armoured vehicles being taken out by drones and artillery fire.
At one point, Russian soldiers mounted on motorbikes try to advance, only to be stopped by Ukrainian fire.
“Our task is to hit them as hard as possible in various areas,” Lemko said. “We focus on our operations, others on theirs, and leadership will negotiate the best possible terms.”
The Azov Corps soldiers are fighting over land that should be handed over to Russia, according to an initial draft of a peace deal proposal between Kyiv and Moscow put forward by the United States. This is despite swathes of the Donbas remaining under Ukrainian control.
But General Oleksandr Syrskyi, the head of the Ukrainian armed forces, has since told Sky News that simply surrendering territory would be “unacceptable”.
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Giving up territory ‘unacceptable’, Ukraine’s military chief says
For Lemko, he says the job of his troops is to inflict as much damage as possible on the Russian side to help strengthen Ukraine’s hand in negotiations.
“Simply giving it [land] away isn’t the way,” he said.
“Diplomats do their work, we do ours. Our job as soldiers is to give as many advantages as possible to our negotiating team. And we’re doing exactly that.”
Lemko, who has been battling against Russia since the Crimean annexation in 2014, also had a warning for the rest of Europe about a rise in hybrid attacks, such as mysterious drone sightings, acts of sabotage and cyber hacks suspected of being linked to Moscow.
He said Ukraine’s experience showed that if attacks by Russia that fall under the threshold of conventional war are not successfully countered, full-scale conflict could follow.
“Ukraine once lost a hybrid war that had been waged since the very start of our independence,” he said.
“Because of that defeat, there was a physical operation against us in Crimea and then a physical operation in 2022.
“Now the hybrid war has reached its climax, and it is moving into the Baltic States and Europe.
“That is why, in my opinion – and in the opinion of most of our officers – now is the moment for all countries to unite and counter this hybrid war. Because the consequence may be a physical one.”
Production: Katy Scholes, security and defence producer, and Azad Safarov, Ukraine producer.