Trump’s unexpected football legacy
A transatlantic moment revisited
As Washington prepares for today’s World Cup draw, the return of the US President to a global football stage has prompted renewed interest in a long forgotten, and rather unusual, episode from 1991. At the time, Trump was best known to the public as a New York real estate figure, not a political one, and certainly not a participant in English football rituals.
The event he joined was a draw for the League Cup, a long running knockout tournament in English club football. For readers less familiar with the sport, cup competitions in England require each round’s matchups to be selected at random, a process often broadcast due to the public anticipation surrounding major pairings.
How a TV crew ended up in Trump Tower
According to The Times, the British television show Saint and Greavsie had traveled to New York while covering the early stages of preparations for the 1994 World Cup, which the United States would later host. The show, presented by former Liverpool forward Ian St John and Tottenham Hotspur legend Jimmy Greaves, often mixed humor with football analysis and was widely watched in Britain at the time.
Producers reportedly attempted to recruit actors Robert De Niro and Woody Allen for a cameo during the League Cup draw segment, but both declined, according to The Times. A producer later encountered Trump at a FIFA reception and, sensing an unexpected opportunity, asked if he would participate. Trump agreed, and the crew was told to bring cameras directly to Trump Tower.
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St John recalled in a 2016 interview with The Guardian that Trump “clearly knew nothing about football” but welcomed the idea of appearing on British television. He described Trump as friendly and more focused on chatting about golf, which was one of his main sporting interests, than discussing any of the clubs involved.
A draw remembered for comedy, confusion, and one explosive pairing
When filming began, Greaves joked about the lavish boardroom setting, comparing it to a famous English football executive’s office, a reference Trump likely did not recognize. The draw itself was overseen by Football League secretary David Dent, with Greaves selecting the home clubs and Trump drawing the away teams.
The moment that has since gained the widest circulation involved the pairing of Leeds United and Manchester United, two of English football’s fiercest rivals. St John reacted with “Ooh, Donald” while Greaves warned that Trump had unknowingly created a high intensity matchup watched closely across Britain.
Trump responded with amusement, saying it “sounds like a game I want to go to.” For many viewers at the time, the contrast between an American businessman unfamiliar with English football and one of the sport’s most heated rivalries created a moment of unplanned comedy.
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After the draw, Trump briefly discussed the state of soccer in the United States, remarking that it had “never really worked out as well” domestically but saying he enjoyed the sport and had played it in high school. The segment ended when Greaves presented him with a novelty mug from the show, which revealed a catchphrase when filled with hot liquid.
According to The Times, Manchester United manager Sir Alex Ferguson later phoned the program’s producer to express frustration, calling the setup a “gimmick.” His team would eventually defeat Leeds and go on to win the 1991, 92 League Cup.
Trump’s new role in a changing football landscape
More than three decades later, Trump’s involvement with football is returning in a very different form. He is expected to participate today in a ceremonial ball draw connected to the 2026 World Cup, which will be jointly hosted by the United States, Mexico, and Canada. FIFA will also present him with its first ever peace prize, according to outlets covering the event, before he delivers remarks on stage.
This moment stands in striking contrast to his 1991 cameo. What was once a television novelty is now a formal appearance at an international sporting ceremony hosted in the country he leads, at a time when football’s popularity in the United States is growing faster than at any point in its modern history.
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