From Brunton Park to Trump Tower: When Carlisle United met Donald Trump

From Brunton Park to Trump Tower: When Carlisle United Met Donald Trump

In 1991, Donald Trump was merely a brash New York tycoon with a penchant for gold-plated décor, long before becoming a political juggernaut and, as fate would have it, now into his second term as President of the United States. Yet rewind over three decades, and we find a curious footballing footnote that connects Trump with Carlisle United — the Cumbrian club who have just taken the unfortunate tumble from League Two into the National League.

What links one of the world’s most controversial figures to a club soon to be battling its way back from non-league obscurity? Enter David Dent, a long-serving football administrator and current honorary president of Carlisle United, who once found himself sat alongside Trump at the top of Trump Tower, overseeing a rather unlikely League Cup draw.

New York, New Balls Please

It’s December 1991. Trump is better known for The Art of the Deal than any political ambition, and the Saint and Greavsie show — ITV’s beloved football magazine programme fronted by Ian St John and Jimmy Greaves — is broadcasting from New York to coincide with the draw for the 1994 World Cup, set to be hosted in the US.

At the same time, ITV needed to televise the quarter-final draw of the League Cup. The problem? Their production crew was already stateside. The solution? Take the draw to the Big Apple — and bring along a man who could ensure it all went smoothly: David Dent, then Secretary of the Football League.

Dent recalls that League Cup draws were alternated between ITV and the BBC at the time. That particular year, ITV had the rights, and they were heading to New York to film the World Cup draw. ITV let him know that unless the League Cup draw happened in New York too, it wouldn’t be shown — and they asked him whether he’d be up for it. His response was conditional but clear: absolutely, as long as they were footing the bill.

A plane ticket, a packed bag and one jet-lagged Football League official later, Dent found himself atop Manhattan’s 58-floor Trump Tower, accompanied by two of football’s most recognisable faces.

“Shall We Ask Donald?”

The set-up was pure showbiz, and ITV weren’t shy in giving it some flair. The YouTube footage — mercifully preserved — opens with St John and Greaves ambling through the streets of Manhattan before arriving outside Trump Tower.

Dent remembers that the show introduced the location with a scene of Saint and Greavsie strolling up to the Trump Tower entrance, acting surprised to find it there. St John posed the idea that they ask Trump if he’d let them do the draw inside. Greaves quipped that they wouldn’t know unless they asked — although, of course, ITV had already confirmed Trump’s participation well in advance.

The boardroom at the top of Trump Tower lived up to every Manhattan cliché. Dent remembers the space being impressively luxurious — full of glitz, gold trimmings, and gleaming glass. It was lavish, certainly, and meticulously styled, if not a little over-the-top.

Greaves, Trump, Dent – and the Balls

As the cameras rolled, the cast assembled. Trump, sporting a full head of hair and a smile a little less taut than today, was introduced as a guest drawer. His job was simple: pick out the away teams. Greaves would draw the home sides, while Dent played the part of the master of ceremonies, reading team names and match details.

Greaves took a moment to remark on the grandeur of the surroundings, saying it was the most extravagant boardroom he’d been in since a visit to Aston Villa’s Doug Ellis. Trump, perhaps familiar with Ellis — or simply amused — roared with laughter.

Trump appeared friendly, courteous, and willing to play along, even if it was abundantly clear that he had absolutely no idea what a League Cup draw entailed. Dent recalls him shaking hands, sitting down politely, and seeming genuinely puzzled about the whole affair — the idea of drawing balls from a bag to determine football fixtures was clearly alien to him.

The actual filming took around an hour. The group sat around the table while the production crew set up, and eventually, Trump arrived, ready to participate in what must have been one of the more surreal moments of his business calendar.

At the time, Trump was widely known as a property magnate with an eye for publicity, but Dent insists there was little indication he would become such a divisive figure in later life. Back then, he came across as a relatively normal bloke, perhaps a little bemused, but far removed from the bombastic persona we’re all too familiar with today.

And then came the moment of the draw — a draw that ended with Leeds United v Manchester United, a powder-keg fixture in any era.

Greaves, quick as ever, responded to the outcome by exclaiming that Trump didn’t realise what he’d just done — a line that has probably been repeated countless times in the years since, under very different circumstances.

Football, Mugs, and Forgotten Moments

After the cameras stopped rolling, Trump made a brief claim of being a football — or, as he put it, “soccer” — enthusiast. He said he’d played it back in his high school days and mused that it would be interesting to see how the World Cup would catch on in the United States.

Before departing, he was presented with a Saint and Greavsie mug, which Greaves declared was one of football’s most prestigious honours — far more exclusive than anything owned by President Bush or Frank Sinatra, he added with tongue firmly in cheek. Trump responded jovially, saying he’d be sure to let them know.

With the mug in hand and the draw complete, Trump departed the boardroom. Dent recalls the wrap-up being quick and uneventful. They packed their things and left the gilded surroundings behind. Since then, a few people have reminded Dent of his encounter with the future US President — a brush with political history tucked away in footballing obscurity.

He’s not particularly aligned with Trump politically and didn’t know him well at the time, but looking back, Dent admits he seems like a very different character now than the man he shook hands with in 1991.

From Bolton to Boardrooms

Dent, born in the Cumbrian village of Bolton near Appleby, became Carlisle United’s first full-time secretary in 1960. His career in football saw him move through the ranks — from Coventry City to the Football League headquarters, eventually serving as League Secretary before stepping down in 2001.

Now in his 80s, he remains a loyal fan of the Blues, hoping for a swift return to the Football League after their recent relegation.

An Unlikely Footnote in Football History

The sight of Donald Trump plucking footballs from a bowl in a glittering New York skyscraper feels like something from a fever dream. Yet it’s real, archived, and an undeniable piece of football folklore. The Cumbrians may now find themselves in the National League with Carlisle United manager Mark Hughes looking to take them straight back up to League Two, but thanks to David Dent, they remain part of one of the most improbable intersections of sport and politics ever filmed.

And perhaps, just perhaps, there’s a Saint and Greavsie mug still sitting somewhere in the White House.