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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0:34
‘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.
In the deep blue waters of the Caribbean, visible from space, an unremarkable grey smudge.
Image: The USS Gerald R Ford seen off the US Virgin Islands on 1 December. Credit: Copernicus
But this is the USS Gerald R Ford: the largest, most deadly aircraft carrier in the world. And it is only part of an armada, apparently set on Venezuela.
Image: The Gerald R Ford, USS Winston S Churchill, USS Mahan and USS Bainbridge in the Atlantic on 13 November. Source: US Department of Defense
From being able to count on one hand the number of warships and boats in the Caribbean, since August we can see the build-up of the number, and variety of ships under US command.
And that’s only at sea – air power has also been deployed, with bombers flying over the Caribbean, and even along the Venezuelan coast, as recently as this week.
Image: A Boeing B-52H Stratofortress near Venezuelan coast from Minot Air Force Base, North Dakota, on 3 December. Credit: FlightRadar24
Sky’s Data & Forensics unit has verified that in the past four months since strikes began, 23 boats have been targeted in 22 strikes, killing 87 people.
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It was the first such strike since 15 November and since the defence secretary, sometimes referred to as secretary of war, Pete Hegseth, came under scrutiny for an alleged “second strike” in an earlier attack.
The US says it carried out the action because of drugs – and there has been some evidence to support its assertion.
The Dominican Republic said it had recovered the contents of one boat hit by a strike – a huge haul of cocaine.
Legal issues
Whatever the cargo, though, there are serious, disputed legal issues.
Firstly, it is contested whether by designating the people on the boats as narcoterrorists, it makes them lawful military targets – or whether the strikes are in fact extra judicial murders of civilians at sea.
And more specifically… well, let’s go back to that very first video, of the very first strike.
What this footage doesn’t show is what came afterwards – an alleged “second strike” that targeted people in the water posing no apparent threat.
And the 4 December strike shows this strategy isn’t over.
The strikes are just part of the story, as warships and planes have headed toward the region in huge numbers.
Drugs or oil?
Some have said this isn’t about drugs at all, but oil.
Venezuela has lots – the world’s largest proven reserves.
Speaking to the faithful on Fox News, Republican congresswoman – and Trump supporter – Maria Salazar said access to Venezuela would be a “field day” for American oil companies.
And Maduro himself has taken up that theme. A few days later, he wrote this letter to OPEC – which represents major oil producing nations – to “address the growing and illegal threats made by the government of the United States against Venezuela”.
That’s how Maduro has framed this – a plan by the US “to seize Venezuela’s vast oil reserves… through lethal military force”.
Lethal military force – an understatement when you think of the armada lying in wait.
And it may be called upon soon. Trump on Tuesday said he’s preparing to take these strikes from international waters on to Venezuelan territory.
Maduro has complained of 22 weeks of “aggression”. There may be many more to come.
Additional reporting by Sophia Massam, junior digital investigations journalist.
The Data X Forensics team is a multi-skilled unit dedicated to providing transparent journalism from Sky News. We gather, analyse and visualise data to tell data-driven stories. We combine traditional reporting skills with advanced analysis of satellite images, social media and other open source information. Through multimedia storytelling we aim to better explain the world while also showing how our journalism is done.
Donald Trump’s bruising assessment of Europe as “weak” and “decaying” is a bitter blow to nations already reeling from the release of his national security strategy.
At the end of the 45-minute interview with Politico, EU leaders might be forgiven for thinking, with friends like these, who needs enemies?
“Europe doesn’t know what to do,” Trump said, “They want to be politically correct, and it makes them weak.”
Image: Trump meets leaders from Ukraine, Germany, France, the UK, Italy, and Finland, as well as the EU and NATO, in August Pic: Reuters
On the contrary, I would imagine some choice words were being uttered in European capitals as they waded through the string of insults.
What has Trump said?
First up, the US president criticised European leaders for failing to end the war between Russia and Ukraine.
“They talk but they don’t produce. And the war just keeps going on and on,” he said.
The fact that the Russians have shown no real commitment to stopping the invasion they started is not mentioned.
Instead, the blame is laid squarely at the feet of Ukraine and its allies in Europe.
“I think if I weren’t president, we would have had World War III,” Trump suggested, while concluding that Moscow is in the stronger position.
Image: Trump meeting European leaders in the Oval Office in August. Pic: @RapidResponse47
Does he have a point?
Critics claim that the White House has emboldened the Kremlin and brought Putin in from the cold with a summit and photo opportunities.
Trump highlights the fact that his return to office forced many European NATO members to increase defence spending drastically.
On this, he is correct – the growing insecurity around how long America can be relied on has brought security into sharp focus.
German Chancellor Friedrich Merz on Tuesday claimed some of its contents were unacceptable from a European point of view.
“I see no need for America to want to save democracy in Europe. If it was necessary to save it, we would manage it on our own,” he told a news conference in Rhineland-Palatinate, the German state where Trump’s paternal grandfather was born.
Image: Meeting between, left to right, Keir Starmer of the UK, Volodymyr Zelenskyy of Ukraine, Emmanuel Macron of France, Donald Tusk of Poland, and Friedrich Merz of Germany. Pic: AP
For this reason, Merz reiterated that Europe and Germany must become more independent of America for their security policies.
However, he noted, “I say in my discussions with the Americans, ‘America first’ is fine, but America alone cannot be in your interests.”
For his part, while Trump said he liked most of Europe’s current leaders, he warned they were “destroying” their countries with their migration policies.
He said: “Europe is a different place, and if it keeps going the way it’s going, Europe will not be…in my opinion, many of those countries will not be viable countries any longer. Their immigration policy is a disaster”.
He added: “Most European nations… they’re decaying.”
Again, the comments echoed his security strategy, which warned immigration risked “civilisation erasure” in Europe.
There’s no doubt immigration is a major concern for many of the continent’s leaders and voters.
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8:11
Zelenskyy meets European leaders
However, irregular crossings into the EU fell 22% in the first 10 months of 2025 according to Frontex, a fact which seems to have passed the president and his team by.
“Within a few decades at the latest, certain Nato members will become majority non-European”, his security document warned.
It also suggested “cultivating resistance” in Europe “to restore former greatness” leading to speculation about how America might intervene in European politics.
Trump appeared to add further clarification on Tuesday, saying while he did not “want to run Europe”, he would consider “endorsing” his preferred candidates in future elections.
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This comment will also ruffle feathers on the continent where the European Council President has already warned Trump’s administration against interfering in Europe’s affairs.
“Allies do not threaten to interfere in the domestic political choices of their allies,” Antonio Costa said on Monday.
“The US cannot replace Europe in what its vision is of free expression… Europe must be sovereign.”
So, what will happen now, and how will Europe’s leaders respond?
If you are hoping for a showdown, you will likely be disappointed.
Like him or loathe him, Europe’s leaders need Trump.
They need the might of America and want to try to secure continued support for Ukraine.
While the next few days will be filled with politely scripted statements or rejections of the president’s comments, most of his allies know on this occasion they are probably best to grin and bear it.
A “cheap ceasefire” between Ukraine and Russia – with Kyiv forced to surrender land – would create an “expensive peace” for the whole of Europe, Norway’s foreign minister has warned.
Espen Barth Eide explained this could mean security challenges for generations, with the continent’s whole future “on the line”.
It was why Ukraine, its European allies and the US should seek to agree a common position when trying to secure a settlement with Vladimir Putin, the top Norwegian diplomat told Sky News in an interview during a visit to London on Tuesday.
“I very much hope that we will have peace in Ukraine and nobody wants that more than the Ukrainians themselves,” Mr Eide said.
“But I am worried that we might push this to what in quotation marks is a ‘cheap ceasefire’, which will lead to a very expensive peace.”
Explaining what he meant, Mr Eide said a post-war era follows every conflict – big or small.
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3:29
Inside Ukraine’s underground military HQ
How that plays out typically depends upon the conditions under which the fighting stopped.
“If you are not careful, you will lock in certain things that it will be hard to overcome,” he said.
“So if we leave with deep uncertainties, or if we allow a kind of a new Yalta, a new Iron Curtain, to descend on Europe as we come to peace in Ukraine, that’s problematic for the whole of Europe. So our future is very much on the line here.”
He said this mattered most for Ukrainians – but the outcome of the war will also affect the future of his country, the UK and the rest of the continent.
“This has to be taken more seriously… It’s a conflict in Europe, it has global consequences, but it’s fundamentally a war in our continent and the way it’s solved matters to our coming generations,” the Norwegian foreign minister said.
Russia ‘will know very well how to exploit vagueness’
Asked what he meant by a cheap ceasefire, he said: “If Ukraine is forced to give up territory that it currently militarily holds, I think that would be very problematic.
“If restrictions are imposed on future sovereignty. If there’s vagueness on what was actually agreed that can be exploited. I think our Russian neighbours will know very well how to exploit that vagueness in order to keep a small flame burning to annoy us in the future.”
Progress being made on peace talks
Referring to the latest round of peace talks, initiated by Donald Trump, Mr Eide signalled that progress was being made from an initial 28-point peace plan proposed a couple of weeks ago by the United States that favoured Moscow over Kyiv.
That document included a requirement for the Ukrainian side to give up territory it still holds in eastern Ukraine to Russia and Mr Eide described it as “problematic in many aspects”.
But he said: “I think we’ve now had a good conversation between Ukraine, leading European countries and the US on how to adapt and develop that into something which might be a good platform for Ukraine and its allies to go to Russia with.
“We still don’t know the Russian response, but what I do know is the more we are in agreement as the West, the better Ukraine will stand.”