The day Donald Trump held the League Cup draw: ‘I’m not sure he knew why we were there’

The first thing you’ll notice is how different he seems. His hair is brown. He appears polite and reserved, a far cry from the imposing, often divisive figure we see today. He’s not even the loudest voice in the room.

It was a rather surreal day in the winter of 1991 when Donald Trump – the man seeking a second term as US President within a week – was a special guest on the British football TV show Saint & Greavsie.

He was there to help with the draw League Cup, EnglandThis is the second domestic knockout tournament, and a three-minute YouTube clip preserves the event. Filmed from the boardroom at the top of the 58-story Trump Tower in Manhattan, where only one man dominates.

“You’ve got some ground here,” Jimmy Greaves, a former England international and one of the country’s greatest goalscorers, tells the host. “It’s amazing – I haven’t seen a boardroom like this since I was at Doug Ellis’s house in Aston Villa“

Trump bursts out laughing. Perhaps he knew that Ellis was Villa’s chairman? Or maybe not.

David Dent, the fourth man at that polished table, can answer that question for Trump three decades later. “I suspect he had no idea who Jimmy was talking about,” he says. Athletic.

In 1991 Dent was secretary of the Football League. As such, he has often presided over League Cup competitions, but never before outside England.

“That season the draw for each round was done at the Saint & Greavsie show,” he explains. “But that Saturday the show was taped in New York because ITV (the channel that broadcast Saint & Greavsie) was also filming the 1994 World Cup draw.

“So ITV came to me and said, ‘We can’t cover the League Cup draw unless you’re in New York.’ Do you like it? They paid the bill, and with two nights at the Waldorf Astoria and a Virgin Atlantic flight, no convincing was needed.”

One transatlantic flight later, Dent was in New York with Greaves and Ian St. John, the former Liverpool And Scotland player. Their double act (St John was the straight man in a comic performance by Greaves) attracted a television audience of almost six million viewers on Saturday lunchtimes.

“I remember the intro to that particular show,” Dent says. “ITV did an episode that started with us walking down Fifth Avenue. When we got to Trump Tower, Ian St. John looked at the building and said, “I wonder if Donald Trump is here today and if he’ll let us hold the draw here.” Greavesy’s response was: “Well, we’ll never know unless we ask.”

“The next shot was of them knocking on the front door of Trump Tower. And the next thing you know, we were all sitting in the boardroom. We had no idea we were talking to the future president of the United States.”

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What the television footage didn’t show was the luck that Trump’s secretary, an Englishwoman, recognized the show’s hosts in the lobby and came over to chat.

When she found out why they were there, she asked if they wanted to meet her boss, and that’s when the show’s producer Bob Patience decided to risk his hand by asking if Trump would enter the prank.

“Suddenly we were carried to the top of Trump Tower,” Dent says. “The first thing that struck me was the luxury. There was gold everywhere. Even the elevators were shiny and shiny. The elevator operator pressed the number, and before he could press the button, we had risen 50-odd floors. I don’t know what speed the elevator was at, but I’ve never known anything like it.”

The atmosphere in the meeting room was light, cheerful and, from Trump’s point of view, perhaps a little confusing. It was clear that the tycoon, then 45, had no idea what was going on. Yet he smiled back from under his trademark slicked-back hair.

Watch the footage and you will see that he is so different from the man we see today, who is now 78 years old and waiting to find out if he will be re-elected president. He was dressed in a dark suit with a dark blue tie and seemed happy to let his guests do most of the talking.

“He was polite and hospitable,” Dent says. “I’m not sure he fully understood why we were there, though. He didn’t know what the draw for the cup meant or what the significance of drawing the ball from the bag was.

“But he made us feel comfortable. We got along well and he was a different person than the one we see now. All the fame and notoriety has completely changed him from what he was back when he was just a New York businessman.”

At the time, the competition was known as the Rumbelows Cup, thanks to a sponsorship deal with an electrical retailer that went bankrupt a few years later. Trump’s goal was to take the visiting teams to the quarterfinals. Greaves was in charge of the draw for the home team. The end result was a little piece of television gold.

Greaves went first, reaching into the green velvet pouch to pull out ball No. 4: Tottenham Hotspur.

Great, Jimmy – home draw for his old club.

Dent handed the bag to Trump. Ball No. 7: Norwich City.

It was a solid but unspectacular start.

If Trump was confused by the next draw, he hid it well: Swindon Town or Crystal Palace against Nottingham Forest or Southampton.

Back to Greaves: No. 2 – Peterborough United.

Over to you, Donald: No. 1— Middlesbrough.

It was the fourth and final draw when Leeds were played at home and the only ball remaining belonged to Manchester Unitedbringing together two fierce rivals who were vying for the First Division title at the time.

(For the record, Alex Ferguson’s side won 3-1 at Elland Road, eliminated Middlesbrough in the semi-final and beat Forest at Wembley… but Leeds won the league.)

The draw prompted a theatrical gasp of “Oooh, Donald!” with a St. John’s Scottish accent, just out of sight. And this was the moment when Greaves leaned towards Trump. “You don’t realize what you’ve done,” he told him.

“This is very important,” Trump responded, perhaps sensing that something exciting had just happened. “This sounds like a game I want to go to.”

When the draw was over, there was time for some small talk. “I’ll tell you what, Donald, are you thinking of opening a store in England?” Greaves wanted to know.

“Well, I think we’re going to go over there and watch a couple of games,” Trump responded in what can only be described as an almighty fib.

“Take my advice,” Greaves said. “You can open one in Leeds, but don’t go to Manchester!”

By this point Greaves was already on a roll. He also took it upon himself to ask Trump if he had ever played football before. “I used to play,” came the answer. “Here we call it football. It’s a great game, I love football, I actually played in high school.”

What did Trump say about holding the 1994 World Cup there?

“It will be interesting to see how it catches on. When you look at England and other countries, they are so big, so incredibly big. But it still hasn’t caught on in the United States. It has begun. “In fact, I see the U.S. women winning the Women’s World Cup, which is really cool.”

Greaves and St John both died 2021but Dent, now in his 80s, lives in Lytham St Annes, Lancashire, where the Football League had its headquarters for many years. And you have to wonder whether Trump realized he was sharing a boardroom with a future president – Dent became honorary president of Carlisle United in 2010, 50 years after becoming their first full-time secretary.

“For Donald Trump, Leeds United versus Manchester United would mean nothing,” says Dent. “He had no idea. But it made for a good story, and I always remember Jimmy giving Trump a Saint & Greavsie mug at the end of the prank.”

This is true. The final shot showed Greaves grinning with delight as he pulled a souvenir gift from behind his chair.

“This is the most prestigious award in the history of football,” he told the future president. “When you pour hot coffee into it, it says ‘It’s a Funny Old Game’ on the side (Greaves’ catchphrase). President Bush or Frank Sinatra don’t have that.”

“I’ll tell them that,” Trump responded. “Good luck in your games.”

A funny old game indeed.

“That mug wouldn’t be worth anything,” Dent says, and now he laughs. “Jimmy presented it as one of the most prestigious things you could ever get. However, I doubt Donald Trump has realized this yet.”

(Top photo: ITV News)