Why Princess Diana still casts a shadow over Donald Trump and King Charles  – Bundlezy

Why Princess Diana still casts a shadow over Donald Trump and King Charles 

Princess Diana is still a background figure in the relationship between Donald Trump and Buckingham Palace according to a royal commentator (Picture: Kate Ingham, Metro/Getty/AP)

While King Charles gives his customary gracious welcome to Donald Trump today, one subject will be strictly off bounds.

The US president, who is being regaled with the red carpet treatment at Windsor Castle on his unprecedented second state visit to the UK, has previously been accused of giving Princess Diana ‘the creeps’, and using the British royals to aggrandise his property interests. 

In 1994, Trump said that the then Prince Charles and his first wife had applied to join his showy Mar-a-Lago resort club in Florida and had each submitted $500,000 (£367,000) membership cheques.  

Follow rolling coverage of Donald Trump’s state visit on Metro’s live blog

The real estate developer was quoted in the New York Times as saying, ‘I handled the applications myself,’ as it seemed the royal couple had become fixtures at the playground for the rich and famous, where sex offender Jeffrey Epstein was among the guests.

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Newly-married Charles and Diana were also rumoured to be buying an apartment at the Trump Tower in New York, bringing royal star power to the brand in the years when it suffered a string of bankruptcies.

The membership claim drew a strong rebuttal from Buckingham Palace.

‘It’s complete nonsense,’ a spokesperson said at the time.

‘They have not joined the club.’ 

New York, UNITED STATES: Britain's Prince Charles (L) talks with Donald Trump (C) and his wife Melania (R) during a reception at the Museum of Modern Art 01 November 2005 in New York. The first official overseas trip since the marriage in April of Prince Charles and his wife Camilla, Duchess of Cornwall, comes 20 years after the frenzy that greeted the US visit of the prince and his then-wife, the late Princess Diana. AFP PHOTO/Timothy A. CLARY (Photo credit should read TIMOTHY A. CLARY/AFP via Getty Images)
Prince Charles (left) talks with Donald Trump and his wife Melania during a reception at the Museum of Modern Art in New York (Picture: AFP via Getty Images)

Trump, who was trying to get Mar-a-Lago off the ground after turning the sprawling residence into a private club, would later clarify that ‘I wrote to them both offering honorary memberships’ but had not heard back.  

‘Prince Charles has been to Mar-a-Lago, and I know he likes it,’ he said.  

Charles politely declined the offer, writing back to say Trump could instead donate to one of his environmental causes, according to the BBC.

In fact, throughout the 1980s and 1990s, stories linking the British royal couple to Trump properties emerged in New York and US tabloids before swirling in media titles around the world.  

In one of the most eyebrow-raising moments in the trio’s relationship, the tycoon is alleged to have pursued Diana in 1994, two years after her separation from Charles was announced.

Diana said ‘he gives me the creeps’ after Trump bombarded her with flowers, according to an account by broadcaster Selina Scott.  

As the lavish reception for the president and First Lady Melania gets underway, his questionable track record in respect of Charles and Diana will not have been forgotten, according to a royal commentator.

King Charles III (left) and US President Donald Trump review the guard of honour during the ceremonial welcome at Windsor Castle, Berkshire, on day one of the president's second state visit to the UK. Picture date: Wednesday September 17, 2025. PA Photo. Photo credit should read: Jonathan Brady/PA Wire
King Charles III and Donald Trump review the guard of honour during the ceremonial welcome at Windsor Castle (Picture: Jonathan Brady/PA Wire)

‘The unique second state visit for an American, which begins today with spectacular pomp and pageantry, is pivotal for the transatlantic relationship,’ Richard Fitzwilliams said.

‘Areas such as trade, security, AI and energy are high on the agenda. 

‘One of Donald Trump’s few consistent qualities has been his admiration for the British royal family. His mother, Mary, was a devoted monarchist. 

‘Yet whilst projecting soft power as their role demands, the royal family will be uncomfortably aware that, according to multiple biographies of Trump, he has used rumours linking his properties with senior royals for his own benefit.’  

Diana The Princess Of Wales Attends A Gala Reception & Preview Of Her 'Dresses Auction' At Christies In London. (Photo by Antony Jones/UK Press via Getty Images)
Princess Diana was allegedly bombarded with flowers by Donald Trump after her split from Prince Charles (Picture: Antony Jones/UK Press via Getty Images)

The New York Times later corrected their story about Charles and Diana becoming members of the exclusive club in Palm Beach.  

Rumours about the princess seeking to buy a $5 million property in the Trump Tower at around the same time also came to nothing.  

A relationship nevertheless existed, with Prince Charles having visited Mar-a-Lago in March 1988, where he attended a cocktail party before moving on to a ranch owned by polo players Geoffrey and Jorie Kent.

The power-hungry tycoon and British royal have met repeatedly over the years, including during Trump’s last state visit in 2019.

What did Diana say about Trump?

Trump saw Diana as the ‘ultimate trophy wife’, according to broadcaster Selina Scott, who was friends with the princess.

Scott recalled sitting next to Diana at a private dinner where she spoke about roses and orchards the property mogul had sent her.

Diana asked ‘what do I do?’ and confided ‘he gives me the creeps,’ according to the journalist.

Scott advised her to throw the flowers in the bin, according to her account in The Times.

However, the rumours about the royals spending big to be part of the Trump world, which came after various businesses in the family name went bankrupt starting in 1991, were a red line for the Palace. 

‘These rumours, all denied by Buckingham Palace, often got enormous publicity which was beneficial to Trump, ’ Fitzwilliams said.  

‘In his 1997 book, Art of the Comeback, Trump said he had only one regret “in the women department”: that he had not had the opportunity to court Diana. The broadcaster Selina Scott claimed he sent bouquets of flowers to the princess at Kensington Palace. She reportedly said he gave her “the creeps”, and his advances got nowhere. 

PALM BEACH, FLORIDA - AUGUST 08: Republican presidential candidate former President Donald Trump speaks during a press conference at his Mar-a-Lago estate on August 08, 2024, in Palm Beach, Florida. Polls currently show a close race between Trump and Democratic presidential candidate, U.S. Vice President Kamala Harris. (Photo by Joe Raedle/Getty Images)
Donald Trump speaks during a press conference at his Mar-a-Lago estate in 2024 when he was the Republican presidential candidate (Picture: Joe Raedle/Getty Images)

‘Such is the tide in the affairs of men that it is Trump, the most powerful man in the world, who holds the trump cards on this visit.

‘However, the royal family will not have forgotten that he involved them in his dubious past history.’ 

Trump revisited the Mar-a-Lago rumour in 1995, telling the New York Post: ‘I didn’t say they signed. I said they were members.’ 

Laurence Leamer, the best-selling American author and journalist, has studied the Palm Beach set through his book, Mar-a-Lago: Inside the Gates of Power at Donald Trump’s Presidential Palace.

Leamer’s insights go some way to revealing why Sir Keir Starmer made such a spectacle of inviting Trump to Windsor Castle — and why it may be Charles who has his fullest attention this week.

President Donald Trump reviews the Guard of Honour after the arrival at Windsor Castle in Windsor, England, Wednesday, Sept. 17, 2025. Kirsty Wigglesworth/Pool via REUTERS
Donald Trump reviews the guard of honour after the arrival at Windsor Castle on September 17, 2025 (Picture: Kirsty Wigglesworth/Pool via Reuters)

‘Charles and Diana didn’t pay to go to Mar-a-Lago, it was just one of the places they visited,’ he told Metro.  

‘Trump loves royalty, because that is what he would like to be, he’d like to be a democratic king, so obviously he is enthralled with them. 

‘He’s turning our classic White House into a palace fit for a king, not a president. Who wants to waste your time on a lousy prime minister when you can be with the king?’

Leamer told Metro that, given the president’s track record with the palace, the scenes he is being treated to behind a huge security cordon represent an astonishing turnaround.

King Charles III and US President Donald Trump during the carriage procession to Windsor Castle, Berkshire, ahead of the ceremonial welcome on day one of the US President's second state visit to the UK. Picture date: Wednesday September 17, 2025. PA Photo. Photo credit should read: Jordan Pettitt/PA Wire
King Charles III and US President Donald Trump during the carriage procession to Windsor Castle in Berkshire (Picture: Jordan Pettitt/PA Wire)

‘He’s the luckiest man who ever lived,’ the author said.

‘If anyone else did what he dared to do, they’d be in prison or they’d be disgraced. He’s an amazing person, he just gets back up no matter what happens. He’s a formidable speaker, he’s mastered a new idiom.  

‘He doesn’t have the presidential gravitas, but with almost half the American people, he’s it.’  

So what is Trump really after as he soaks up the reception in Windsor before moving on to meet the prime minister at his Chequers grace-and-favour retreat in Buckinghamshire? 

‘It’s all about him getting all of the attention,’ Leamer said.

‘He’s the ultimate narcissist and again, he’s the would-be king.

‘The king of the world, that how he looks at things.’  

Metro has approached the White House for comment.  

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