When Donald Trump Entered the World of English Football

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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.

An Accidental Encounter Turns Into TV Gold

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.