Mr Churchill hosted US Envoy Joseph Davies and Ambassador John Winant at Chequers in 1945
Mr Churchill hosted US Envoy Joseph Davies and Ambassador John Winant at Chequers in 1945 (Picture: Alamy)
WWII

PM to give Trump personal tour of Sir Winston Churchill's legacy at Chequers

 Mr Churchill hosted US Envoy Joseph Davies and Ambassador John Winant at Chequers in 1945
Mr Churchill hosted US Envoy Joseph Davies and Ambassador John Winant at Chequers in 1945 (Picture: Alamy)

US president Donald Trump is set to be treated to a personal viewing of Sir Winston Churchill's archives at Chequers, the Prime Minister's country residence, as part of the government's charm offensive during his historic second state visit.

Mr Trump is a known admirer of Mr Churchill, proudly keeping a bronze bust of Britain's former wartime leader in pride of place in the Oval Office at the White House.

So what more might he learn about how Mr Churchill spent his time at Chequers and the significance of American wartime ties to the picturesque English country estate?

Trump's fascination with Churchill 

Immediately after the inauguration for his second term in January 2025, President Trump reinstated a bust of Winston Churchill in the Oval Office.

It had also been displayed there during his first term, although it was moved elsewhere in the White House by both Presidents Biden and Obama, much to Mr Trump's frustration.

There are, in fact two bronze sculptures of Mr Churchill in the White House.

One was created in 1965, soon after Churchill was made an honorary US citizen.

The second, by Sir Jacob Epstein, was initially loaned to President George W Bush, and then presented to President Trump by former prime minister Theresa May in 2017.

Mr Trump is said to draw personal inspiration from Churchill and likes to draw comparisons with him. 

The film The Darkest Hour, depicting the story of Mr Churchill's life, is thought to be one of his favourite films.

Former Prime Minister formally loaned President Trump a bust of Winston Churchill in 2017
Former prime minister Theresa May formally loaned President Trump a bust of Winston Churchill in 2017 (Picture: Alamy)

Churchill's connection to Chequers

According to the book Chequers, by former prime minister John Major's wife, Norma Major, Mr Churchill was very much at home at his official rural residence.

He spent a significant amount of time there, particularly during the Second World War – enjoying the change of pace, although sometimes working until the early hours of the morning on wartime planning.

Churchill also wrote and broadcast many key wartime speeches from Chequers, writing propped up in bed and rehearsing his lines pacing the garden.

He was usually accompanied by close family members on his visits, and his grandson, Winston Spencer Churchill, was born in the house in 1940 and baptised at the local church.

Mr Churchill even brought his black cat, Nelson, along to Chequers and allowed him to sleep at the foot of his bed.

Sir Winston Churchill relaxing at Chequers in 1953
Sir Winston Churchill relaxing at Chequers in 1953 (Picture: Alamy)

Chilly wartime welcome for VIP American guests

When he visits Chequers, President Trump will be following in the footsteps of many wartime American dignitaries who met Mr Churchill there, including two envoys of US President Roosevelt, Joseph Davies and Harry Hopkins, as well as the American ambassador to the UK during World War Two, John Winant.

However, American guests at that time unfortunately discovered that despite its ornate surroundings, the house was draughty and cold in winter.

"Churchill virtually lived in his siren suit and only the very hardy arrived at Chequers without warm pyjamas and extra underwear," wrote Norma Major.

Mr Hopkins, although enchanted by the surroundings, suffered in particular.

"His method of keeping warm was… to wrap up in his overcoat and huddle in a ground-floor cloakroom, the only room small enough to benefit from any body heat he might generate."

The government hopes President Trump will appreciate the surroundings at Chequers as well as its ties to his hero Mr Churchill
Chequers gives President Trump beautiful surroundings and historic ties to his hero Mr Churchill (Picture: Alamy)

A much warmer welcome planned for Trump

President Trump is unlikely to suffer similar discomfort when he meets with Sir Keir Starmer for bilateral talks at Chequers, with every effort made to ensure the visit runs smoothly.

He can also enjoy the exclusivity of viewing Churchill's memories at Chequers, as the building is otherwise not open to the public.

However, as Mr Churchill discovered during the Second World War, the house is easily spotted from surrounding hillsides and requires extra security to protect a high-level leader.

In 1940, Coldstream Guards were positioned along the driveway, with anti-aircraft guns on hilltops, barbed wire around the perimeter and a spotter's hut on the roof above his bedroom.

President Trump can expect an even higher level of protection during his visit – a tall metal barrier has been specially built around the site, roads closed, and the surrounding airspace shut down.

The government will be hoping the meeting has a positive outcome and leaves the US president with fond memories of another connection to his hero, Sir Winston Churchill.

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