How Princess Diana could have been Donald Trump’s First Lady… if the billionaire hadn’t given her the creeps

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Those who were there still recall how dazzling Diana was that night. She wore diamond and pearl drop earrings and a velvet gown that was alluringly low-cut.

Princess Diana during the charity event.
Princess Diana during the charity event.

Some 900 of New York’s most powerful movers and shakers had gathered at the Hilton Hotel in Manhattan for a glittering $1,000-a-plate charity dinner. It was December 1995, and fate had placed Donald Trump on the princess’s table, although his second wife Marla was also present.
Diana had greeted him and other major donors earlier at the reception. She’d already met the tycoon several times, mostly at charity functions, but didn’t know him well, although he’d offered her complimentary membership of his Florida country club, Mar-a-lago — an offer she declined.
She was certainly well aware of his reputation with women, though he had never made a pass at her. For his part, Trump had noted Diana’s qualities in some detail.

Princess Diana at the charity event in Manhattan, 1995.
Princess Diana at the charity event in Manhattan, 1995.

As he wrote in his book, The Art Of The Comeback, published in November 1997, three months after her death: ‘I couldn’t help but notice how she moved people. She lit up the room. Her charm. Her presence. She was a genuine princess — a dream lady.’
Totally unaware of how he felt, you can imagine Diana’s surprise soon after she and Charles were divorced in July 1996 — six months after that Manhattan dinner — to receive a huge basket of flowers from Trump.

They were for her 35th birthday. Clearly the lascivious billionaire was making the princess an exception to his locker-room maxim that ‘it’s checkout time’ for women once they reach the age of 35. (Of course, history then could have taken a very different course. If they had hit it off, she might now be about to move into the White House as America’s First Lady — never having dated Dodi Fayed with such tragic consequences.)

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This week, however, it emerged how, two months after Diana was killed in that car crash in Paris, Trump talked about her with rather less respect than he showed in the book. Rather, she was a potential sexual target.
At the time, he was a guest on an American radio show presented by ‘shock jock’ DJ Howard Stern and he boasted, on air, that he ‘could and would’ have slept with Diana.
‘You could have nailed her,’ suggested the DJ crudely, to which Trump replied: ‘I think I could have . . . She had the height, she had the beauty, she had the skin.’