Three months and three days from today, Donald Trump could become President of the United States. Who would have predicted this when he met another president – the honorary president of Carlisle United?

Today is the first day of the new Football League season.

Carlisle begin their campaign with the long trip to Portsmouth.

But let’s rewind almost quarter of a century, to a curious football story which brings together a United stalwart and one of the most controversial men in the world.

In December 1991 Donald Trump was a successful businessman. Already wealthy, but not the brash, divisive figure who could soon become the most powerful person on the planet.

ITV football programme Saint and Greavsie was in New York to cover the draw for the 1994 World Cup.

This episode also featured the draw for the quarter-finals of an English football competition, the League Cup.

YouTube has preserved the occasion. A three-minute clip shows presenters Ian St John and Jimmy Greaves in a boardroom at the top of Manhattan’s 58-story Trump Tower.

Also around the table, sitting next to each other, are Donald Trump and David Dent.

Dent was born in the village of Bolton, near Appleby. In 1960 he was appointed Carlisle United’s first full-time secretary.

By 1991 he was secretary of the Football League. In this capacity he often presided over the League Cup draw.

Now in his 70s and retired, Dent lives in Lancashire. Six years ago he was appointed Carlisle’s honorary president.

Still a keen supporter of the Blues, he is looking forward to the first home match of the season next Tuesday night.

This is against Port Vale in the League Cup... the competition that brought him together with Donald Trump.

So how did a Cumbrian come to share a boardroom table with the possible next US president?

Dent recalls: “We did all the League Cup draws on TV. Some seasons it was ITV, some the BBC.

“That season the draws for each round were made on the Saint and Greavsie Show.

“In 1994 the World Cup was going to be played in America. The draw for the group stages was being made in New York on a Saturday at the end of 1991.

“ITV decided they would record the show in New York so they could cover the World Cup draw. They said ‘We can’t cover the League Cup draw unless you go to New York. Do you want to do that?’

“‘Yes, we’ll do that if you’re paying the bill.’”

One transatlantic flight later, Dent was in New York with Ian St John and Jimmy Greaves.

The YouTube clip begins in Trump Tower’s boardroom.

Dent recalls how their presence here was explained on screen.

“ITV filmed this sequence where we were walking down the street in New York. Saint and Greavsie came to this great big sign: ‘Trump Tower’. Ian St John says ‘I wonder if Donald Trump would let us do the draw here?’

“Jimmy Greaves says ‘We won’t find out unless we ask him.’”

Trump’s agreement had, of course, already been secured.

The ITV contingent was whisked to the top of Trump Tower, which Dent remembers as “very impressive, very lavish. It just seemed very well-finished and glitzy. A lot of gold plating and polished glass.”

The atmosphere in the boardroom appears jovial on the YouTube clip.

“This is some pad you’ve got here,” said Jimmy Greaves to his host. “I haven’t seen a boardroom like this since I was at Doug Ellis’s at Aston Villa.”

Donald Trump roared with laughter. Perhaps he knew that Doug Ellis was the chairman of Aston Villa? Or perhaps not.

For the League Cup draw Greaves drew the home teams, Trump the away teams.

Dent read out some information about the draw, and revealed which team was represented by each ball pulled from the bag.

“We were in there for maybe an hour,” he says. “We just sat around the table, got the cameras set up, then Donald Trump came in and we did the draw.

“At that time he was an up and coming entrepreneur. He was fairly well known. I don’t think anybody then could see the kind of guy he eventually became.

“He was just a normal guy. He came and shook hands. He hadn’t got any idea what we were doing. He didn’t know what the draw for a cup competition meant, what the significance of pulling a ball out of a bag was.”

The last tie to be drawn brought two fierce rivals together: Leeds United v Manchester United.

“You don’t realise what you’ve done there!” said Jimmy Greaves.

This may not be the last time someone has said those words to Donald Trump.

The contrast between the 1991 Trump and today’s Republican Presidential candidate is striking.

Trump, then aged 45, appears polite and reserved, nothing like the scowling, raging figure we see today.

Was he acting that day in the boardroom? Is he acting now? Or maybe 25 years have changed him.

After the draw Trump claimed to be a fan of football; or soccer, as he explained it’s called in America.

“It’s a great game,” he said. “I played it in high school.”

What did he make of the 1994 World Cup being played there?

“It will be interesting to see how it catches on in the United States.”

Trump was presented with a Saint and Greavsie mug.

“This is the most prestigious award in footballing history,” claimed Greaves. “President Bush or Frank Sinatra haven’t got one of those.”

“I’ll tell them!” said Trump.

He shook hands with David Dent, and this strange chapter in the life of Carlisle United’s president was over.

“He disappeared, we packed our bags and came out,” says Dent.

“A few people have seen the clip and reminded me that I’ve met him.

“I can’t say I’m a supporter of him. I didn’t know him at all then. But he seems to be a different character now.”

David Dent fact file

1937: Born at Bolton, near Appleby

1960: Appointed Carlisle United’s first full-time secretary

1978: Joins Coventry City as secretary

1984: Moves to the Football League as deputy secretary, under future Football Association chief Graham Kelly

1989: When Kelly leaves the League, Dent is appointed Football League secretary

2001: Retires

2010: Returns to Carlisle as United’s honorary president