At the same location a week ago, May finally won agreement for her Brexit plans from her cabinet after two years of internal wrangling, but within days, two senior ministers had quit, departures which Trump said earlier in the week had left Britain in "turmoil".
"It was from right here at Chequers that Prime Minister Churchill phoned President Roosevelt after Pearl Harbor", Trump said, referencing the surprise attack by the Japanese on December 7, 1941, that plunged the US into World War II.
Fresh from sending North Atlantic Treaty Organisation into crisis talks and ahead of a summit with Kremlin chief Vladimir Putin, Trump shocked Britain's political establishment when he criticised May's plans for ties with the European Union after Britain leaves in March.
Pointing to May, Trump said "this incredible woman right here is doing a fantastic job, a great job", and added that the United States is looking forward to finalising a "great" bilateral trade agreement with the UK.
"She is a very smart, very tough, very capable person, and I would much rather have her as my friend than my enemy".
"Whatever you do is OK with us, just make sure we can trade together, that's all that matters".
And, what about the so-called special relationship that supposedly links the British and American governments?
In the interview, Trump said that Theresa May had ignored his advice on Brexit.
"I said very good things about her" in the interview, Trump said. "I would have done it much differently".
Trump followed a similar pattern at this week's North Atlantic Treaty Organisation summit by slamming US allies at the outset but ultimately claiming North Atlantic Treaty Organisation was stronger than it was before.
"The relationship is further back than it was a few days ago", Dr. Jacob Parakilas, deputy head of the USA and Americas program at London-based think-tank Chatham House, told Xinhua in an exclusive interview on Friday.
"The Chequers agreement reached last week provides the platform for Donald and me to pursue an ambitious deal that works for both countries right across our economies", May said in defence of her controversial Brexit strategy.
"The reaffirmation of the British-U.S. relation we saw at the press conference will probably assuage some of the doubts we have seen about the status of the relationship", Parakilas said.
Conservative party MP Sarah Wollaston said Trump was "determined to insult" May, adding: "If signing up to the Trump world view is the price of a deal, it's not worth paying". "Very complicated negotiation, and not an easy negotiation, that's for sure", Trump added, in what appeared to be a further attempt to appease the British prime minister.
Meanwhile, mass protests are being held against Trump in London over his maiden visit as the US President to the United Kingdom.
Arriving straight from a North Atlantic Treaty Organisation summit that was predictably contentious, the U.S. president has been greeted with massive protests on his first trip to London since taking office.
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Former New York Knicks teammates Patrick Ewing and Charles Oakley before an National Basketball Association game in 2016. Casino regulators in Nevada are accusing former New York Knicks star Charles Oakley of gambling fraud.
Thousands take to London streets to protest Trump
The sting was greater for the fact that May was using the dinner to pitch her case for a separate trade arrangement. The Trumps entered the castle's Quadrangle by Range Rover after arriving on the castle grounds by helicopter.
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