Donald Trump may have been welcomed to the UK with a rare second state visit, but his history with the Royal Family has been far from smooth — particularly when it comes to the late Princess Diana.

The US president, accompanied by First Lady Melania Trump, attended a lavish banquet at Windsor Castle before meeting Sir Keir Starmer at Chequers on 18 September. While commentators picked apart Melania’s oversized hat and Trump’s frequent lapses in royal protocol, others revisited the president’s often uneasy past with Britain’s royals.

Criticism of Kate and Meghan

Trump has never shied away from voicing blunt opinions about members of the monarchy. He previously described Meghan Markle as “terrible” and “nasty,” while she had branded him “divisive” and “misogynistic” during his 2016 campaign.

In 2012, Trump also criticized Kate Middleton after a paparazzo photographed her sunbathing topless in France. “Kate Middleton is great – but she shouldn’t be sunbathing in the nude – only herself to blame,” he tweeted at the time, a remark that drew heavy backlash.

The Diana Rumor and Trump Tower

But Trump’s most eyebrow-raising connection is with Princess Diana. Between 1981 and 1983, reports circulated that Diana and Prince Charles were considering a $5 million apartment in Trump Tower. Buckingham Palace swiftly dismissed the rumors as false.

Speculation grew that Trump himself had spread the story to generate publicity for his new Manhattan skyscraper. Former royal press secretary Dickie Arbiter later told the BBC: “People have been doing it since the year dot, getting publicity through the royals. They will make outrageous comments and unless it’s libellous, the royals won’t do anything about it. Never explain, never complain is their mantra.”

In his 1987 memoir The Art of the Deal, Trump admitted he neither confirmed nor denied the rumor when asked by a journalist, but conceded that the buzz helped bring attention to Trump Tower.

Controversial Remarks About Diana

Trump faced further criticism years later when he made controversial comments about Diana during a 2000 interview with Howard Stern, three years after her tragic death. Asked if he would have slept with her, Trump responded: “Without even hesitation. She was truly beautiful and people don’t realise how beautiful. She was crazy, but these are minor details.”

The remarks sparked outrage, though Trump softened his stance years later. In a 2016 interview with Piers Morgan, he said: “I did respect her, but no interest from that standpoint. But I did meet her once, and I thought she was lovely.”

From rumors tied to his real estate ventures to blunt and often offensive remarks, Trump’s history with the Royal Family — especially Diana — has long been a source of controversy. Even as he enjoys the honor of a second state visit, his past comments continue to cast a shadow over his royal encounters.