Trump-Starmer talks could be landmark moment – and join pantheon of UK-US summits
In years to come, it may become known simply as Chequers ’25.
But today’s summit between Sir Keir Starmer and Donald Trump, at the prime minister’s country retreat, has the potential to be a landmark moment in UK-US history.
There’s plenty of scope for it to go horribly wrong, of course: over Jeffrey Epstein, Sir Keir’s pledge to recognise Palestine, the president’s lukewarm support for Ukraine, the Chagos Islands sell-off, or free speech.
Trump state visit live – read the latest
But on the other hand, it could be a triumph for the so-called “special relationship” – as well as relations between these two unlikely allies – with deals on trade and tariffs and an improbably blossoming bromance.
Either way, this Chequers summit – on the president’s historic second state visit to the UK – could turn out to be one of the most notable one-to-one meetings between PM and president in 20th and 21st century history.
Sir Keir and Mr Trump have already met several times, most recently at The Donald’s golf courses in Scotland in late July and, before that, memorably at the White House in February.
Donald Trump and Keir Starmer wave as they board Air Force One on a previous trip. Pic: AP
It was then that the PM theatrically pulled King Charles’s invitation for this week’s visit out of his inside pocket in a spectacular stunt surely masterminded by the “Prince of Darkness”, spin doctor-turned-ambassador (until last week, anyway) Peter Mandelson.
And over the years, there have been some remarkable and historic meetings and relationships, good and bad, between UK prime ministers and American presidents.
From Churchill and Roosevelt to Eden and Eisenhower, from Macmillan and JFK to Wilson and Johnson, from Thatcher and Reagan, to Blair and Bush, and from Cameron and Obama… to Starmer and Trump, perhaps?
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‘History’ that binds the UK and US
A brief history of relationships between PMs and presidents
Throughout UK-US history, there have been many examples of a good relationship and close bond between a Labour prime minister and a Republican president. And vice versa.
Also, it has not always been rosy between prime ministers and presidents of the two sister parties. There have been big fallings out: over Suez, Vietnam and the Caribbean island of Grenada.
Leading up to this Chequers summit, the omens have not been good.
First, the PM was forced to sack his vital link between Downing Street and the Oval Office, Lord Mandelson, over his friendship with Epstein.
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Trump meets Starmer: What can we expect?
Second, the president arrived in the UK to a barrage of criticism from London mayor Sir Sadiq Khan, who accused him of doing more than anyone else to encourage the intolerant far right across the globe.
And third, in a video-link to the “Unite the Kingdom” march in London last weekend, one-time Trump ally Elon Musk called for a dissolution of parliament and a change of government and appeared to encourage violent protest.
Churchill and FDR
Churchill and FDR at the White House in 1941. Pic: AP
Back in the mid-20th century, the godfather of the “special relationship” was wartime leader Sir Winston Churchill, though it was 1946 before he first coined the phrase in a speech in the US, in which he also spoke of the “iron curtain”.
It was in 1941 that Churchill held one of the most significant meetings with a US president, Franklin D Roosevelt, at a Washington conference to plot the defeat of Germany after Japan’s attack on Pearl Harbour.
Churchill arrived in Washington in December after a rough 10-day voyage on a Royal Navy battleship and stayed three weeks, spending Christmas in the White House and on Boxing Day becoming the first UK PM to address Congress.
The close bond between Churchill and Roosevelt was described as a friendship that saved the world. It was even claimed one reason the pair got on famously was that they were both renowned cigar smokers.
Churchill and Truman
Churchill and Truman catch a train from Washington in 1946. Pic: AP
After the war ended, Churchill’s “special relationship” speech, describing the alliance between the UK and US, was delivered at Westminster College, in Fulton, Missouri in March 1946.
The speech was introduced by president Harry Truman, a Democrat, with whom Churchill had attended the Potsdam Conference in 1945 to negotiate the terms of ending the war.
These two were also close friends and would write handwritten letters to each other and address one another as Harry and Winston. Mr Truman was also the only US president to visit Churchill at Chartwell, his family home.
Eden and Eisenhower
Eden and Eisenhower shake hands at the conclusion of their three-day conference in 1956. Pic: AP
But the transatlantic cosiness came to an abrupt end in the 1950s, when Churchill’s Conservative successor Anthony Eden fell out badly with the Republican president Dwight Eisenhower over the Suez Crisis.
Mr Eden did visit Mr Eisenhower in Washington in January 1956, and the official record of the meeting describes the discussion as focussing on “policy differences and Cold War problems”.
Macmillan and JFK
Harold Macmillan and John F Kennedy at Andrews Air Force Base. Pic: AP
But in the early 1960s, a Conservative prime minister and a Democrat president with seemingly nothing in common, the stuffy and diffident Harold Macmillan, and the charismatic John F Kennedy, repaired the damage.
They were credited with rescuing the special relationship after the rupture of the Suez Crisis, at a time of high tensions around the world: the Berlin Wall, the Cuban missile crisis, and the threat of nuclear weapons.
The two leaders exchanged handwritten notes, as well as Christmas and birthday cards. The Macmillans visited the Kennedys twice at the White House, in 1961 and 1962 – the second described in the US as a “momentous” meeting on the Cuban crisis.
The relationship was abruptly cut short in 1963 by Supermac’s demise prompted by the Profumo scandal, and JFK’s assassination in Dallas. But after her husband’s death, Jacqueline Kennedy was said to have had a father-daughter relationship with Macmillan, who was said to have been enchanted with her.
Wilson and LBJ
Johnson meeting with Wilson. Pic: Glasshouse Images/Shutterstock
After JFK, the so-called special relationship cooled once again – and under a Labour prime minister and Democrat president – when Harold Wilson rejected pressure from Lyndon B Johnson to send British troops to Vietnam.
Mr Wilson became prime minister in 1964, just two months after LBJ sent US troops. His first overseas trip was to the White House, in December 1964, and the PM returned to tell his cabinet: “Lyndon Johnson is begging me even to send a bagpipe band to Vietnam.”
Thatcher and Reagan
Thatcher at Reagan’s 83rd birthday celebrations. Pic: Reuters
And even though Margaret Thatcher and Ronald Reagan were ideological soulmates, Thatcher was furious when she wasn’t consulted before the Americans invaded Grenada in 1983 to topple a Marxist regime.
Even worse, according to Mrs Thatcher’s allies, a year earlier, Reagan had stayed neutral during the Falklands War. Reagan said he couldn’t understand why two US allies were arguing over “that little ice-cold bunch of land down there”.
Thatcher and Reagan became firm friends. Pic: Reuters
But their relationship didn’t just survive, it flourished, including at one memorable visit to the presidential retreat at Camp David in 1984, where Reagan famously drove Mrs T around in a golf buggy.
They would also memorably dance together at White House balls.
Blair and Bush
Blair hosts Bush in Durham in 2003. Pic: PA
Camp David was also where, in 2001, Republican president George W Bush and Labour’s Sir Tony Blair embarked on the defining mission of his premiership: the Iraq War. It was to prove to be an historic encounter.
The war was the turning point of Sir Tony’s decade in Number 10. He was branded a liar over claims about Saddam Hussein’s “weapons of mass destruction”, he was vilified by the Labour left, and it was the beginning of the end for him.
And to add to the suspicion among Sir Tony’s critics that he was Mr Bush’s poodle, in 2006 at a G8 summit in St Petersburg – that wouldn’t happen now – a rogue microphone picked up the president calling, “Yo, Blair! How are you doing?”
Cameron and Obama
Cameron and Obama serve food at a barbecue in the garden of 10 Downing Street. Pic: Reuters
Some years later, the Tory prime minister sometimes called the “heir to Blair”, David Cameron, bonded over burgers with the Democrat president Barack Obama, serving a BBQ lunch to military families in the Downing Street garden. They also played golf at the exclusive Grove resort in 2016.
They seemed unlikely allies: Obama, the first African-American president, and Cameron, the 19th old Etonian prime minister. It was claimed they had a “transatlantic bromance” in office. “Yes, he sometimes calls me bro,” Lord Cameron admitted.
But not everything went well.
The Tory PM persuaded Mr Obama to help the Remain campaign in the 2016 Brexit referendum, when he claimed the UK would be “at the back of the queue” on trade deals with the US, if it left the EU. It backfired, of course.
Now it’s Sir Keir Starmer’s turn to tread a delicate and potentially hazardous political tightrope as he entertains the latest – and most unconventional – US president.
The greatest dangers for Sir Keir will be a news conference in the afternoon, in the gardens, if the weather permits.
Good luck, as they say, with that.
Before then, there’s the potential for what the Americans call a “pool spray”, one of those impromptu, rambling and unpredictable Q&As we’ve seen so many times in the Oval Office.
For Sir Keir, what could possibly go wrong?
Chequers ’25 could be memorable and notable, like so many previous meetings between a PM and a president. But not necessarily for the right reasons for this UK prime minister.
Imagine moving to a country you’ve never been to before, with a culture you have no knowledge of and with a language you’re unable to speak. You’re with your whole family, including three children. And your new home, not your old one, is at war with its neighbour.
Well, that’s exactly what the Hare family did, who relocated to Russia from the United States two years ago because they felt “persecuted”.
“We were noticing a great upsurge in LGBT-type policies coming into the government, especially the school system,” Leo Hare says.
“This is where we drew a line in the sand,” his wife Chantelle adds. “This is a complete demonic attack against the conservative Christian families.”
The devout Christians, who have three sons aged 17, 15 and 12, describe themselves as “moral migrants”.
I’m chatting to them at their apartment in Ivanovo, a city 150 miles from Moscow. It’s a big change from Texas, where the family lived on a farm and had their own shooting range.
But in a country where so-called “LGBT propaganda” is banned, they say they feel safer than before.
Leo and Chantelle Hare
“There are laws that say: ‘no you can’t just run wild and have gay pride parades and dance in front of all the children’. You can’t do this. I like this,” Leo tells me.
The family was granted asylum last year in a ceremony that was covered on state TV. But as unusual as their story may sound, the Hares aren’t the only ones who have turned to Russia in search of sanctuary.
According to the latest figures from Russia’s interior ministry, 2,275 Westerners have applied for a new shared values visa, which was introduced by Vladimir Putin last August.
It’s aimed at those who think the West has become too woke.
Citizens from countries Russia considers unfriendly (which includes Britain, the US and most of the EU) are offered a three-year residency permit without meeting any language requirements or skills criteria.
On the ninth floor of a skyscraper in Moscow’s financial district, a group of adults are holding pens in their mouths and making strange noises.
We’re observing a Russian language class that’s been put on by an expat club to help its members integrate into the local society.
A Russian language class
Among those with the bit between their teeth is British national Philip Port from Burnley, Lancashire.
He runs a visa agency for those going in the opposite direction – Russians to the UK – and has been coming to Russia on and off for 20 years. He says he applied for the shared values visa for both practical and ideological reasons.
“I love Russia,” he tells me unapologetically, describing it as “safe as houses”.
“There’s no crime, the streets are clean, it’s well-developed,” he adds.
Philip Port from Burnley
His view of the UK is nowhere near as complimentary.
“I’m all for gay rights, don’t get me wrong, but I think when they’re teaching them to children in school – I’ve got a seven-year-old son, I don’t want him being influenced in that way.”
It’s unclear how many British nationals have migrated to Russia under the shared values visa, but Philip Hutchinson, whose company Moscow Connect helps Westerners apply for the pathway, says he receives between 50 and 80 inquiries a week from the UK.
“There’s a huge amount of people that are frustrated by the way the country’s got in,” he tells me. “Taxes keep going up and up and up. And we’re giving all this money to Ukraine.”
Mr Hutchinson stood as a candidate for the Conservative Party in last year’s local elections in Britain.
He moved to Moscow earlier this year after his Russian wife was unable to obtain a UK visa, bucking a trend that saw most Western expats flee Russia after its invasion of Ukraine in February 2022.
I ask him if the war bothers him or his clients.
“It doesn’t,” he answers without hesitation. “As far as I’m concerned, I’m not getting involved in that. You know, I’m not here to deal with politics.”
Read more from Sky News:
How is Britain’s immigration system actually changing?
Everything we know about China’s new ‘super embassy’
But is politics at play here?
After arriving in Russia, many of the “ideological immigrants” post slick videos on social media about how wonderful their new life is.
The Hare family was granted asylum last year in a ceremony that was covered on state TV
One prominent American blogger called Derek Huffman, who moved to Russia with his family from Arizona, has even joined the Russian army to fight in Ukraine.
It’s the perfect PR for a country that markets itself as a beacon of conservative values, and as the antidote to moribund, Western liberalism. But Russia insists it’s not running a recruitment campaign.
“We don’t give any social security guarantee or any free housing,” says Maria Butina, the Russian lawmaker spearheading the shared values programme.
“People come on their own with their own money, own families, at their own expense.”
Not everyone’s had a positive experience, though. The Hares say they were scammed out of $50,000 (£38,200) by the family who initially put them up when they arrived in Russia.
And their two oldest sons have returned to America, because of problems finding a school. The family weren’t aware that children are required to speak Russian to be eligible for a state education.
So, do they regret moving here?
“Moving so fast? Probably,” Leo admits.
“At times though, your pathway in life takes you places you wouldn’t have willingly gone. But through God and providence, you’re meant to go through this.”
President Donald Trump says he would “love to see” one-time ally Marjorie Taylor Greene return to politics one day – as the fiery congresswoman reportedly considers a White House run in 2028.
The US leader said “it’s not going to be easy for her” to revive her political career in comments to Sky’s partner network NBC News.
But he added: “I’d love to see that.”
In the meantime, Mr Trump said “she’s got to take a little rest”.
Marjorie Taylor Greene wearing a MAGA cap last year. Pic: AP
Marjorie Taylor Greene – a one-time MAGA ally who has turned into a fierce critic of Mr Trump – unexpectedly announced on Saturday that she would be resigning from Congress.
In a video posted online, the Georgia representative said she did not want her congressional district “to have to endure a hurtful and hateful primary against me by the president we all fought for”.
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Marjorie Taylor Greene attacks Trump in resignation video
Ms Greene’s resignation followed a falling-out with Mr Trump in recent months, as the congresswoman criticised him for his stance on files related to Jeffrey Epstein, along with foreign policy and health care.
Mr Trump branded her a “traitor” and “lunatic” and said he would endorse a challenger against her when she ran for re-election next year.
She said her last day would be 5 January 2026.
Meanwhile, Time magazine reports that Ms Greene has told allies that she is considering running for president in 2028.
There is a profound sense of deja vu surrounding the Ukraine crisis right now.
It was only a few months ago that European leaders rushed to Washington after Donald Trump appeared to align with Vladimir Putin at their Alaska Summit.
The Europeans gathered in Washington in August and appeared convinced that they had pulled Trump back around to their mindset: that unity and strength, not capitulation, is the answer for Ukraine.
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Mark Stone on how Ukraine peace plan came about
Well, this week it is possible (some sources say probable) that European leaders will again head to Washington for another attempt to pull Trump back.
Ukraine live: Trump suggests peace plan ‘not final offer’
Ukraine and its allies head to Geneva
The meeting in Geneva on Sunday is absolutely pivotal.
It was billed initially as a meeting between the Americans and the Ukrainians.
But it has since morphed into a wider meeting with a number of European countries sending senior officials.
The core meeting is still expected to be between US envoy Steve Witkoff and the Ukrainians, but sideline talks will now take place with a much wider group of nations.
Many European leaders have spoken to President Trump on Friday and Saturday and plan to do so again.
I am told Keir Starmer’s conversation with him was “good, short but productive.”
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PM: ‘More to do’ on peace plan
Britain’s national security adviser, Jonathan Powell, will be in Geneva.
Over the last nine months, he has emerged as an important British influence on the Trump administration. He is close to Witkoff – who co-wrote or at least signed off on the 28-point plan.
However, the Powell-Witkoff relationship is clearly not close enough to have afforded the UK a heads-up on this latest peace plan.
Kirill Dmitriev and Steve Witkoff during a meeting in Saint Petersburg, Russia, in April. Pic: Reuters
‘Sudden injection’
One source told me that the “sudden injection” by the Americans had “been surprising.”
The American decision to put a rocket under the quest for peace in Ukraine appeared to have vice president JD Vance’s fingerprints on it.
The territorial elements of the peace plan are almost identical to a proposal put forward by Vance in the summer of 2024 before Trump won the election.
Read more:
Trump’s 28-point Ukraine peace plan in full
Battle for frontline towns where Ukraine’s soldiers are surrounded
Starmer reveals Trump peace plan ‘concern’ at G20
Vance’s stance on Ukraine has always leant towards questioning the point of it all. He led the attacks of Volodymyr Zelenskyy at the Oval Office in February.
The US secretary of the army, Dan Driscoll, who has taken a lead in the conversions with Ukrainian officials, is a friend and ally of Vance – the two were at Yale together.
Vance has also been leading calls for his own administration to spend more time on “the home front”.
This sudden momentum on Ukraine could be an attempt to draw a line under it quickly in order to focus attention domestically.
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Trump: ‘I’d like to get to peace’ in Ukraine
The week ahead
So – things to look out for now: first, the Geneva meeting on Sunday – this is pivotal and will set the tone and the agenda for the days ahead. It is day-by-day at the moment.
Out of the Geneva meeting, a meeting of the European “coalition of the willing” countries will convene.
And following that, a contingent of European leaders heading to Washington seems likely – perhaps on Tuesday.
By Wednesday, America begins to wind down for the biggest holiday of the year – Thanksgiving.
Trump’s deadline for an agreement by Thanksgiving still feels improbable, but it’s not impossible that some sort of memorandum of understanding could be signed by then.
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This would ensure momentum remains in the process and Trump is kept encouraged on progress.
He has suggested that the deadline is movable, and that the deal proposed in the 28-point plan is not the final one.
Notwithstanding all this, there is no question that this moment, for Ukraine and for Europe, is perilous and ominous.
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