But standing alongside Mrs May after the meeting at her country residence, Mr Trump praised her as an "incredible woman" and a "very tough negotiator" who was "doing a fantastic job", and said there could be a "great" trade deal between the United States and UK.
It's been a tumultuous few days for May having had two senior ministers resign in protest at her plans for trade with the European Union after Britain leaves the bloc next March.
And fortunately we tend to record stories now so we have it for your enjoyment if you'd like it, but we record when we deal with reporters.
Trump, who has compared the June 2016 referendum in which a majority of British voters supported leaving the European Union to his own election that year, accused May of abandoning British voters with her Brexit plans.
"The fact that [the blimp] may cause offense to somebody isn't a good reason to deter the hard-fought rights of freedom of speech and freedom of expression", the mayor said.
He added: "I actually told Theresa May how to do it but she didn't agree, she didn't listen to me". He paid a brief visit to the USA ambassador's central London residence before taking a helicopter to Blenheim Palace ― the monumental house where Winston Churchill was born― for a lavish dinner event with British Prime Minister Theresa May. He also criticized immigration and said London Mayor Sadiq Khan had failed to stop terrorism.
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Think your friends would be interested? Britons, he said, "like me a lot", the BBC reported. I'm sorry, I was wrong to say the things that I said would be an apology. "I'd like to see them be able to work it out so it could go quickly, whatever they work out". "It was, I think, a celebration of the very special relationship the United States had".
Looking ahead to his meeting with Russian president Vladimir Putin on Monday, Trump said he would be discussing many topics but his biggest hope was an agreement to substantially reduce nuclear proliferation - his ultimate dream was to get rid of the weapons altogether, he said.
Mr Trump used the interview with the Sun to lay into Mr Khan, who criticised the American leader as "ill-informed" over a tweet following the London Bridge attack in June 2017. I haven't been there in a long time.
Ambassador Johnson sought to play down Trump's comments.
London Mayor Sadiq Kahn, who gave the go-ahead to fly a giant baby Trump balloon in the city, has defended the protesters.
More than 64,000 people signed up to demonstrate in London against the visit and other protests were expected in major cities around the country. Look at what is going on in London. "But it is too bad what is going on", the president said. "You have a mayor who has done a awful job in London".
At Chequers, Trump and May will discuss foreign policy, according to White House officials.
The president also hit out at immigration into Europe, linking it with crime. But at the Chequers news conference, Trump said he had been responding to the Sun's question about Johnson as a possible prime minister, adding: "He has been very nice to me".