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.

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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.

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?

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.

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

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

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

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

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

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

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”.

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

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

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.

The pomp and circumstance. The man who some say wants to be king, meets The King.

Trump and King Charles spend the day together. We digest what’s happened, why it’s happened, and what it all means.
You can also watch all episodes on our YouTube channel.

Email us on trump100@sky.uk with your comments and questions.

US talk show host Jimmy Kimmel has had his programme pulled over “offensive and insensitive” comments about Charlie Kirk.

Kimmel used his show on Monday night to accuse Donald Trump and his allies of “doing their best to fan the flames” following the conservative influencer’s assassination last week.

The comedian told his audience “many in MAGA land are working very hard to capitalise on the murder of Charlie Kirk”.

He added the president’s response to Mr Kirk’s death “is not how an adult grieves the murder of someone he called a friend”.

Disney-owned ABC said it would be taken off-air indefinitely – and with immediate effect – after network operator Nexstar said it would stop broadcasting the programme.

Andrew Alford, president of Nexstar’s broadcasting division, said it “strongly objects” to Kimmel’s comments.

“Mr Kimmel’s comments about the death of Mr Kirk are offensive and insensitive at a critical time in our national political discourse,” he said, with the show to go off-air to “let cooler heads prevail”.

Mr Trump welcomed the news on Truth Social, writing “congratulations to ABC” and “Kimmel has ZERO talent”.

But Kimmel’s suspension has triggered outrage from Democrats like California Governor Gavin Newsom, who posted on X: “The @GOP [Republican Party] does not believe in free speech. They are censoring you in real time.”

Senate minority leader Chuck Schumer called for people “across the political spectrum… to stop what’s happening to Jimmy Kimmel”.

What happened?

Kimmel called out what he believes is hypocrisy in how Republicans have responded to Mr Kirk’s death.

Mr Trump and Vice President JD Vance are among those to cite “left-wing extremism” as a factor in the killing.

In a separate Truth Social post in the early hours of Thursday, the president – who is in the UK for his state visit – announced the anti-fascist Antifa movement would be designated as a terrorist organisation.

Mr Kirk’s suspected killer, Tyler Robinson, appeared in court for the first time on Tuesday. Prosecutors said he had shared negative views about Mr Kirk, an influential media figure in the MAGA movement.

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On the Monday edition of his show, Kimmel drew attention to Capitol rioters who “wanted to hang” Mr Trump’s first term vice president, Mike Pence, for certifying Joe Biden’s 2020 election win.

“Was that the liberal left? Or the toothless army who stormed the Capitol on January 6,” said Kimmel.

His remarks saw the chairman of the Federal Communications Commission, Trump backer Brendan Carr, threaten to “take action” against Disney and ABC.

A representative for Kimmel did not immediately respond to a request for comment about the cancellation.

Celebrities who have guested on his show joined Democrats in speaking out. Wanda Sykes accused Mr Trump of seeking to end freedom of speech, while Ben Stiller tweeted: “This isn’t right.”

The latest season of Jimmy Kimmel Live averaged 1.57 million viewers per episode, according to media research firm Nielsen – and the show’s YouTube channel has almost 21 million subscribers.

Kimmel follows in Colbert’s footsteps

The abrupt removal of Jimmy Kimmel Live comes after fellow late night host Stephen Colbert saw his programme cancelled, which fans claimed was a result of his criticism of Mr Trump.

Mr Trump presents himself as a staunch advocate of free speech, but regularly rails against media organisations which criticise him. This week he launched a lawsuit against The New York Times.

CBS announced in July it would end The Late Show when its current series ends next May.

In a statement, the network said the move was “not related in any way to the show’s performance, content or other matters happening at Paramount.”

Mr Trump praised the move, saying “his talent was even worse than his ratings”.

Colbert’s Late Show won an Emmy for outstanding talk series for the first time at the weekend.