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.