In one of the most surreal moments captured on British television, a younger, more reserved Donald Trump found himself helping with an English football draw. It was 1991, and The Football Newsletter is taking you back to the day Trump, then just a New York real estate mogul, became an unexpected guest on Saint & Greavsie, the iconic football show.

Trump’s setting was the boardroom of Trump Tower, an opulent space filled with marble and gold accents that, at the time, made him the picture of understated wealth rather than controversy. Back then, he was light-hearted, polite, and far less the divisive figure we know today. The football stars he was with, legendary British hosts Jimmy Greaves and Ian St John, seemed worlds away from his business empire, but for a few minutes, they all shared the same screen, creating an unforgettable moment in football TV history.

Here’s how it happened: the League Cup draw was typically made on Saint & Greavsie, but that season, ITV had flown to New York to film the 1994 World Cup draw. David Dent, then the secretary of the Football League, was invited along, and said, “ITV came to me and said, ‘We can’t cover the League Cup draw unless you are in New York. Do you fancy that?’ With two nights at the Waldorf Astoria and flying Virgin Atlantic, it didn’t take much convincing.”

Dent, Greaves, and St John arrived at Trump Tower, where a chance meeting with Trump’s English secretary led to a bold request: would her boss join the draw? Astonishingly, Trump agreed, and they were swiftly whisked up 58 floors to the gleaming boardroom where he awaited them.

In footage preserved on YouTube, Trump appears bemused but gracious, a world apart from the bombastic persona he’d later adopt. Greaves kicked things off, pulling Tottenham as the first home team, before passing the bag to Trump. His first pick? Norwich City.

To the hosts, the draw’s significance was obvious, but for Trump, it was all a bit of fun. “He was polite and welcoming,” Dent says. “I’m not sure he fully understood why we were there or the meaning behind pulling a ball out of a bag, but he went along with it. He was a different person then, just a New York businessman.”

When the draw brought Leeds United and Manchester United together, the hosts were delighted, gasping, “Ohhh, Donald!” Trump, looking pleased, nodded as if to say he’d somehow been part of something big. “That sounds like the game I’d want to go to,” he said with a grin. To him, it was just another day in his boardroom, but for The Football Newsletter and football fans everywhere, it was an iconic moment.

Greaves and St John kept up the humour, asking Trump if he might ever consider opening a store in England. Trump, chuckling, replied that he’d like to, adding, “I might even catch a game.” Greaves, quick-witted as always, advised, “Open one in Leeds, but don’t go to Manchester!” Trump laughed, playing along.

Then came the final flourish. Greaves presented Trump with a Saint & Greavsie mug, calling it “the most prestigious award in footballing history.” “President Bush or Frank Sinatra don’t have one of these,” he added with a wink. Trump accepted the mug, promising, “I’ll tell them that.” It was a cheeky gesture, but for The Football Newsletter, it captures a wonderfully quirky moment in football history.

Reflecting on the day, Dent, now in his 80s, shared that the draw was an unlikely brush with fame for everyone involved. “Leeds United versus Manchester United, to Donald Trump, would not have meant a single thing,” he laughs. “He probably didn’t understand how special that rivalry was, but it made for a great story.”

What remains so captivating is Trump’s unexpected willingness to join in, despite knowing little about the game. This encounter between British football legends and a New York businessman represents a unique moment of cross-cultural charm, and for The Football Newsletter, it’s one of those unlikely stories that reminds us of football’s global reach.

The footage, still available online, is a time capsule of Trump before politics—a quieter, less complicated figure—and a reminder that sometimes, football’s funniest moments happen off the pitch. So did Trump keep that mug? Dent has his doubts, “Jimmy made it sound like one of the most prestigious things you could ever receive, but I doubt he still has it.”

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