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

The first thing you notice is how different he seems. His hair is chestnut brown. He appears polite and reserved, nothing like the imposing, often divisive figure we see today. He is not even the biggest voice in the room.

It was the rather surreal day in winter 1991 when Donald Trump — the man bidding to win a second term as U.S. president in a week’s time — was the special guest on the UK football TV show Saint & Greavsie.

He was there to help with the draw for the League Cup, England’s secondary domestic knockout tournament, and a three-minute clip on YouTube preserves the occasion. Filmed from the boardroom at the top of Manhattan’s 58-storey Trump Tower, there is only one man dominating the room.

“This is some pad you’ve got here,” Jimmy Greaves, the former England international and one of the country’s greatest goalscorers, says to his host. “This is beautiful – I haven’t seen a boardroom like this since I was in Doug Ellis’ at Aston Villa.”

Trump rocks with laughter. Perhaps he knew that Ellis was the chairman of Villa? Or perhaps not.

David Dent, the fourth person behind that polished table, can answer that question on Trump’s behalf three decades on. “I suspect he wouldn’t have had a clue who Jimmy was talking about,” he tells The Athletic.

In 1991, Dent was the secretary of the Football League. As such, he often presided over the League Cup draw — never before, though, outside England.

“That season, the draw for each round was made on the Saint & Greavsie show,” he explains. “But on that particular Saturday, the show was recorded in New York because ITV (the channel which broadcast Saint & Greavsie) were also filming the draw for the 1994 World Cup.

“So ITV came to me and said, ‘We can’t cover the League Cup draw unless you are in New York. Do you fancy that?’ They footed the bill and, with two nights at the Waldorf Astoria and flying Virgin Atlantic, it didn’t take a lot of persuasion.”

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 to Greaves’ comic turn — used to pull in television audiences of almost six million viewers on Saturday lunchtimes.

“I remember the intro to this particular show,” says Dent. “ITV filmed a sequence that started with us walking down Fifth Avenue. When we got to Trump Tower, Ian St John looked up at the building and said, ‘I wonder if Donald Trump is in today and whether he’d let us do the draw here’. Greavsie’s response was, ‘Well, we’ll never know unless we ask’.

“The next shot was 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 clue we were talking to the future president of the United States.”

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What the TV footage did not reveal was the stroke of good fortune that involved Trump’s secretary, who was English, recognising the show’s hosts in the lobby and going over for a chat.

When she found out why they were there, she asked if they would like to meet her boss and that was when the show’s producer, Bob Patience, decided to chance his arm by asking if Trump would take part in the draw.

“All of a sudden, we were being whisked to the top of Trump Tower,” says Dent. “The first thing that struck you was the opulence. There was gold everywhere. Even the lifts were sparkly and glitzy. The lift attendant pressed the number and, no sooner had he pressed the button, we had gone up 50-odd floors. I don’t know what speed the lift was, but I’d never known anything like it.”

Donald Trump and his then-fiancee Marla Maples in 1991 (Timothy A. Clary/AFP via Getty Images)

The atmosphere in the boardroom was light and jovial and, from Trump’s point of view, maybe a bit bewildering. It was obvious the tycoon, then 45, had no real idea what was going on. Yet he smiled back from beneath his trademark back-combed hair.

Watch the footage back and he seems so different to the man we see today, now 78 and waiting to find out if he is being re-elected as president. He wore a dark suit with a navy tie and seemed happy to let his guests do most of the talking.

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

“But he made us feel comfortable. We got on well and he was a different person to the one we see now. All the publicity and fame has changed him completely from how he was back then, when he was just a New York businessman.”

The competition was known at the time as the Rumbelows Cup, thanks to a sponsorship deal with an electrical retailer that went out of business a few years later. Trump’s job was to pull out the away teams for the quarter-finals. Greaves was in charge of drawing the home teams. The end result was a little piece of television gold.

Greaves went first, sticking his hand into a green velvet bag to pull out ball No 4: Tottenham Hotspur.

Nice one, Jimmy — a home draw for his old club.

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

It was a solid yet unspectacular start.

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

Back to Greaves: No 2 — Peterborough United.

Over to you, Donald: No 1 — Middlesbrough.

It was the fourth, and final, tie when Leeds were drawn at home and the only remaining ball belonged to Manchester United, pitching together two fierce rivals who were competing for the First Division title at the time.

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

The draw prompted a theatrical gasp of “Ohhh, Donald!” in St John’s Scottish accent, just out of view. And that was the moment Greaves leant towards Trump. “You don’t realise what you’ve done,” he told him.

“That’s a biggie,” Trump replied, perhaps sensing something exciting had just happened. “That sounds like the game I want to go to.”

Gary Speed scored for Leeds against Manchester United in the 1991-92 League Cup, but his side were beaten (John Giles/PA Images via Getty Images)

With the draw completed, there was time for a bit of small talk. “I tell you what, Donald, are you thinking of opening a store in England?” Greaves wanted to know.

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

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

By now, Greaves was 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 reply. “We call it soccer here. It’s a great game, I love soccer, I played actually in high school.”

What did Trump make of the 1994 World Cup being held there?

“It will be interesting to see how it catches on. When you look at England and other countries, it’s so big, so incredibly big. But in the United States, it hadn’t really caught on until now. It’s starting. In fact, I see the United States women won the World Cup for women, which is really great.”

Greaves and St John both died in 2021, but 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 realised he was sharing his boardroom with a future president — in 2010, Dent was made honorary president of Carlisle United, 50 years after becoming their first-ever full-time secretary.

Ian St John and Jimmy Greaves in their pomp in 1990 (Steve Etherington/EMPICS via Getty Images)

“Leeds United versus Manchester United, to Donald Trump, would not have meant a single thing,” says Dent. “He wouldn’t have had a clue. But it made for a good story and, at the end of the draw, I always remember Jimmy presenting Trump with a Saint & Greavsie mug.”

It’s true. The final flourish involved Greaves, grinning with delight, pulling out a souvenir gift from behind his chair.

“This is the most prestigious award in footballing history,” he told the future president. “When you pour your hot coffee in it, it’s got ‘It’s a Funny Old Game’ (Greaves’ catchphrase) on the side. President Bush or Frank Sinatra haven’t got one of those.”

“I’ll tell them that,” Trump replied. “Good luck with the games.”

A funny old game, indeed.

“That mug wouldn’t have cost anything,” says Dent, and he is laughing now. “Jimmy made it sound like one of the most prestigious things you could ever receive. Yet I doubt Donald Trump has still got it.”

(Top photo: ITV News)