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Why Trump loves Churchill: From Oval Office bust to Starmer jibe

Who was Winston Churchill? What has Keir Starmer said about him, and when has Donald Trump detailed his admiration for the British wartime leader?

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Trump Baby blimp flying next to a statue of Winston Churchill in Parliament Square during an official visit by the US President to London
The Trump baby protest balloon flying next to the statue of Churchill in London. Picture: Alamy

By William Mata

Donald Trump has hit out at Sir Keir Starmer once more over a perceived lack of support for America’s action in Iran, this time saying the prime minister “is no Winston Churchill”.

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The president vented his anger after the US was initially denied access to the UK-controlled Diego Garcia airbase on the Chagos Islands to launch the Iranian airstrikes.

Sir Keir eventually allowed the American military to use the base, but has been reluctant to endorse the strikes, even as the UK now readies its HMS Dragon after strikes in Cyprus.

The PM said: “President Trump has expressed his disagreement with our decision not to get involved in the initial strikes, but it is my duty to judge what is in Britain’s national interest.

"That is what I have done, and I stand by it.”

But after stating on Monday he was “very disappointed,” with Sir Keir, Mr Trump has now doubled down with his Churchill comments in signs the special relationship is not well.

Mr Trump told reporters: "That island that you read about, the lease, for whatever reason, he made a lease of the island, somebody came and took it away from him.

"And it's taken three, four days for us to work out where we can land, it would have been much more convenient landing there as opposed to flying many extra hours.”

"This is not Winston Churchill we're dealing with."

winston churchill
Winston Churchill was the UK prime minister during the second world war. Picture: Alamy
Review of the Year 2017: January: Prime Minister Theresa May meets US President Donald Trump as he points to a bust of Sir Winston Churchill in the Oval Office of the White House, in Washington DC, USA.
Donald Trump shows then prime minister Theresa May the Churchill bust in 2017. Picture: Alamy

Donald Trump’s admiration of Winston Churchill

Donald Trump has made his feelings known about Winston Churchill a number of times, with his jibe to Sir Keir Starmer being the latest.

June 2020: Lafayette Square incident

While in his first term, Donald Trump was criticised for using tear gas and riot control tactics at Lafayette Square amid peaceful George Floyd demonstrations in Washington DC.

The president had ordered the way to be cleared for a photo op, and press secretary Kayleigh McEnany compared his visit to Churchill overseeing bombing damage.

September 2020: Downplaying Covid-19

Mr Trump said at the height of the pandemic that he was taking a calm approach to dealing with Covid-19, downplaying the virus and comparing himself to Churchill.

He said: "When Hitler was bombing, I don't know if you know this, when Hitler was bombing London, Churchill, great leader, would often go to a roof in London and speak.

"And he always spoke with calmness. He said we have to show calmness. No, we did it the right way and we've done a job like nobody."

January 2025: Churchill bust

A bust of Churchill has been a political football between presidencies, with Barack Obama removing it from the Oval Office, with Mr Trump bringing it back in 2017 and then 2025 - after Joe Biden had also removed it.

Jacob Epstein's bronze statue, designed in 1945, is now often seen next to Mr Trump when he gives speeches in the office.

ELLESBOROUGH, ENGLAND, UK - 18 September 2025 - British Prime Minister Sir Keir Starmer with US President Donald Trump at the PM's official country residence at Chequers in Buckinghamshire, England, U
Sir Keir alongside Donald Trump at Chequers in the 2025 State Visit. Picture: Alamy

What are Keir Starmer’s views on Winston Churchill?

Sir Keir has shown his appreciation for Churchill in upgrading his London statue in Parliament Square to war memorial status, which will see anyone who defaces it given a greater punishment.

He said at the time: “The justifiable fury that is provoked when people use his statue as a platform for their protests speaks to the deep and enduring love that all decent British people have for Sir Winston.”