The Trump I (barely) know

I can’t say I know the new President of the United States very well, but during the five years I lived in New York between 1995 and 2000 we were on nodding terms. That is to say, when I turned up at a party and he was there too, we would politely acknowledge each other. This was for two reasons, neither of which reflects particularly well on me.

The first is that I was briefly the party columnist for Vanity Fair, deciding whose photos should appear in the monthly roundup. Donald Trump was keen for his picture to appear as often as possible, obviously, hence the nod. The second and more important reason is that my girlfriend for some of that time was Lucy Sykes, a British “It Girl” that Trump had a soft spot for. He would actually cross the room to talk to her.

Trump had been married to Marla Maples, but they separated in 1997, and after that he was footloose and fancy-free. He certainly had an eye for the ladies, scanning the room for potential conquests. I remember being told by someone who worked with him on The Apprentice that its producer Mark Burnett — now Trump’s “special envoy” to the UK — employed someone referred to as the “Trump Whisperer,” whose job was to calm him down whenever he was about to lose his temper. Apparently the most effective method was to persuade an attractive young woman to cross the room in his peripheral vision. “Who’s that?” he’d ask, forgetting about whatever it was that had annoyed him.

Lucy is the source of my favorite Trump story. She was in Pastis having lunch with her friend Lloyd, an English lawyer, when she noticed Trump at another table. They waved at each other and, on his way out, he stopped by to say hi.

“What are you up to this afternoon?” she asked.

“I’m flying to England,” Trump said.

“That’s a coincidence,” she replied. “My friend Lloyd is going to England this afternoon, too.”

That was something she was well aware of, because Lloyd had arranged for a taxi to meet him at the restaurant and kept checking his watch, worried about being late.

“Really?” said Trump, looking at Lloyd. “You wanna ride?”

“No, it’s OK,” Lloyd said. “I’ve booked a taxi.”

Trump looked at him, shrugged his shoulders as if to say, “suit yourself,” and left the restaurant.

“Are you mad?” asked Lucy as soon as he’d gone.

“Why did you turn him down?”

“I don’t need a ride to the airport.”

“He wasn’t offering you a ride to JFK, you numpty. He was offering you a ride in his private jet.”

Realization dawned and Lloyd leapt from his seat and ran out of the restaurant, hoping to catch Trump before he climbed into his waiting limo. But it was too late. The billionaire property tycoon had vanished.

My final Trump story was told to me by my friend Alex Connock, who did manage to hitch a ride on a private jet with The Donald, although not on his Boeing 757, known as Hair Force One. This was back in 1990 and Alex was working as a cub reporter for People magazine, having recently graduated from Columbia Journalism School. He was sent to Atlantic City to cover the opening of the Taj Mahal, Trump’s biggest casino to date, and the morning after the launch he was woken in his hotel room at nine by a phone call from the great man. Trump was evidently worried that Alex didn’t have enough color for his story and asked if he’d like to accompany him and a “friend” on a trip to Indianapolis. This was on a private jet belonging to Akio Morita, the co-founder of Sony.

The “friend” turned out to be Michael Jackson, who was a Sony recording artist. Jackson had shown up at the Taj Mahal the day before and invited Trump to accompany him on a trip to visit a sick child seven hundred miles away; Trump asked Alex along. So my friend found himself sitting opposite the future president of the United States and the King of Pop.

The best moment was when Jackson handed Trump the National Enquirer, which he opened up, revealing the front-page story was all about him. Alex’s camera was in front of them on the table and a picture of Trump and Jackson sitting side by side on Morita’s jet reading the Enquirer would have been priceless. But he didn’t want to seem like a bottom-feeding journalist, so restrained himself, a decision he’s regretted ever since.

Had I found myself in that situation, I would have handed the camera to a steward, shoehorned myself between them and asked for a group portrait. Today, I’d be hawking that photo round various publishing houses, trying to sell a quickie book called My Friend, the President. But then, I am a shameless hack, which is probably why Trump didn’t want to risk being more than a nodding acquaintance.

Read Cosmo Landesman on Toby Young — page 65. This article was originally published in The Spectator’s March 2025 World edition.