So much winning: Donald Trump and the sports industry

Perhaps no American president has taken office with as deep a history in sport as Donald Trump. Over more than three decades his misadventures in the industry encapsulated the myth and misanthropy of an American icon, part of a pitiless quest for validation that would end, somehow, in the Oval Office.

So much winning: Donald Trump and the sports industry

Gold, chemical symbol Au, is among the least reactive of the elements. While not quite inert, it is highly resistant to oxidation and corrosion. Those properties, combined with its capacity to conduct electricity, have given rise to a range of modern industrial uses but historically, it was prized for different reasons.

A rare metal that did not tarnish easily had obvious merit as a symbol of value, and just as important was its relationship with light. Gold shines. It reflects glory.


A little over three decades ago, long before settling on putting the public to his service, a wealthy young New York property scion named Donald Trump decided to bask in the ownership of a football team.

The New Jersey Generals had gone 6-12 in the opening season of the United States Football League (USFL), a startup competition that took the pro game past the limits of the National Football League (NFL) and college seasons and on into the springtime. Despite that losing record, the Generals had the makings of a glamour team, not least with Heisman Trophy-winning running back Herschel Walker in their ranks. The University of Georgia underclassman had skipped senior year and the big league place that would follow, signing a contract worth an annual US$4.2 million.

The Generals’ majority owner was J Walter Duncan, an Oklahoman who had made his money in oil and gas. One season with the new team was time enough for the novelty to wear off, and he sold to Trump in time for 1984. According to reports, the fee was US$9 million. According to Trump, it was US$5 million.

The USFL had been designed according to the Dixon Plan, a blueprint envisaged by league founder David Dixon. Patience was its underlying principle. The Dixon Plan called for big-market teams that would be attractive to broadcasters – ABC and ESPN bought the rights to the opening season for a combined US$13 million. But Dixon also expected owners to incur early losses and wanted a commitment to the project, to fiscal responsibility, and to spring football.

By the time Trump arrived on the scene, an informal salary cap had already been popped open – Herschel Walker’s contract alone was worth three times the initial agreed limit. As teams across the league found it difficult to keep control of their finances, some owners became more tempted by the prospect of going from the slow build to the quick fix – and the dynamic new force in their midst was keen to supply the latter.

“If God had wanted football in the spring,” Trump said, “he wouldn’t have created baseball.” With an eye on a merger that might just make him an NFL owner before long, he pushed his peers towards accepting a switch to an autumn schedule. They duly did, with a majority agreeing to make 1985 the last spring season of the USFL.

The move did not go well. Several teams chose to relocate rather than face competition in their respective cities. With a series of big markets moving out of the picture, the league’s TV deal was under threat. The 1986 season was suspended.

There was one play left, an antitrust lawsuit against the NFL for restricting the trade of its upstart competitor. On 29th July 1986, a six-person jury found that the NFL was operating an unfair monopoly but saw cause to award only nominal damages, rather than the US$567 million sought. In 1990, long after it ceased operations, the USFL received a cheque for US$3.76 – a buck in compensation, tripled under antitrust laws, and adjusted for interest.

In 1987, Donald Trump released The Art of the Deal.

A postscript: Trump would later participate in a documentary by director Mike Tollin, who had earlier run the USFL’s production company. On camera, Trump dismisses the league as a footnote in an illustrious career. He calls it “small potatoes” – giving the film its title.

Tollin’s thesis is clear enough: that however big or starchy it might have become, the USFL’s slim chances of survival were curtailed by Trump’s influence. Still, he was grateful for the property magnate’s involvement, and sent him a formal invitation to an early screening.

The letter came back, signed by the hand that would one day approve executive orders, a message scrawled across it in marker pen.







The USFL episode set a pattern that will be familiar to students of other Trump business ventures – the steaks, the vodka, the airline, the glossy magazine, the casinos, the ‘university’. Yet through the shortfalls and the debts and the bankruptcies of the 1980s and 1990s, one brand somehow stayed intact: Donald J Trump.

A classic magic trick is comprised of three parts. First there is the pledge, where the performer shows an audience an ordinary person or object. Then comes the turn, where something unexpected happens. Finally, there is the prestige, where the object is restored but the secret is retained.

Trump’s magic worked differently. He would enter a scene where his wealth and status were a source of some excitement. He would point to some property and say that this could be the biggest business in the world – bigger even – and that he would make it so. Then, as the extraordinary conspired not to happen, Trump himself would disappear.

All was never quite as it seemed with Trump in the sports business. In the late 1980s, the now-shuttered Trump Plaza in the New Jersey gaming centre of Atlantic City was the venue for a series of prize fights in a boom time for professional boxing. Trump drew close to the major players of the age, Don King chief among them. Always one to take rules and regulations in the spirit in which he intended, Trump set himself up as the ‘host’ of these events. In Las Vegas, he would have required a licence as a live-site promoter.

Among other things, the looser arrangement allowed Trump to make the most of an ‘advisory’ relationship with Mike Tyson – whom he would later support through a trial and conviction for rape – without disclosing its details. He may have been concealing a conflict of interest, of any enticement to have the world heavyweight champion fight at his casinos. He may even have had a paucity of interest – in other words, there could have been no formal relationship. The upshot was the same, either way: Trump got ample airtime with another of the great media phenomena of the decade.

As Trump’s profile rose, and his coffers quietly emptied, his approach was evolving. In 1987 he took a meeting with Mike Packer, a CBS basketball commentator and entrepreneur who had been encouraged by a colleague to launch a multi-stage cycling race. The Trump Organisation became its title partner.

The Tour de Trump ran for the first time in 1989 and promised a glitzy but still competitive pro cycling experience, and an event that could soon become a US counterpart to Europe’s grand tours. Greg LeMond, the first American winner of the Tour de France, raced in the ten-stage opening edition. But no man was more associated with it than its sponsor, whose waterfront casino was the climactic backdrop.

At the time, Trump claimed an initial reluctance to attach his name to the race but said his “instinct” had led him to relent.

In May 1989, he told The New York Times: “I said, ‘I’ll take heat,’ but then I also said, ‘It’ll also make it successful.’ That is what is going to make this race successful. You can’t say much yet in the sense of being honoured, but I am honoured. Because the race, not even having been held, has already exceeded any expectations we’ve had. In revenues. In excitement.”

According to that interview, Trump had committed to a US$750,000 guarantee that he now believed he would never have to pay, given the commercial interest that had followed his name to the race. But for all the media attention the tour had generated, it would only last two years in its original guise. Trump was going broke, his businesses underperforming and his credit drying up. He withdrew in 1990, though the race continued for a few more years under another name synonymous with big American business – DuPont.

Trump had always been a fiend for publicity and by now he had realised, by intent or dumb, blind luck, that he was his own most valuable asset. His track record outside of real estate suggests he had no business starting businesses. He lacked the judgement, the patience, the head for detail and the sense for nuance. But he had discovered the knack of projecting wealth, and of attaching himself to projects that could do that for him.

As the comedian John Mulaney put it early in Trump’s primary run, “To me, Trump is not a rich man. Donald Trump is like what a hobo imagines a rich man to be.”

Trump would not be the first or the last man of means to realise that sport was an environment in which his fortune would garner headlines with lower scrutiny. He would one day be tenuously linked with bids for Scottish soccer club Rangers and Colombian soccer club Atlético Nacional – once bankrolled to great success by drug kingpin Pablo Escobar. In 2014 he publicly announced his interest in buying the Buffalo Bills – and the chance to finally become an NFL owner – and pledged to prevent a rumoured relocation. His reported US$1 billion bid fell well short but it meant people were talking about Trump, and his money.  

That construct – the big-thinking fixer and doer who millions of Americans might trust to lead them, whatever views he espoused – is one he then crystallised in entertainment, through a string of cameos as himself in film and television, and, of course, NBC’s The Apprentice. He also turned to sports entertainment, and the WWE.

Trump brought WrestleMania to Atlantic City twice, in 1988 and 1989, and returned to subsequent editions as a spectator. By 2007 he had woven himself into the series’ narrative, taking on WWE president Vince McMahon in a bizarre proxy match, a ‘Battle of the Billionaires’ – note, not ‘hundred-millionaires’ – that ended with Trump shaving McMahon’s head.

Trump was inducted to the WWE Hall of Fame in 2013. The one time he was linked with a direct business interest– through a fake press release issued to promote a guest storyline in which he ‘bought out’ McMahon – the company’s stock dropped seven per cent.


Somewhere along the way, Trump found golf.

In many respects, it is a natural fit. Throughout his business career he has only really had two dependable sources of income: property development and service fees, and licensing. An interest in golf courses, as Richard Gillis wrote last year in Golf International, was ‘a logical next step’ – not least for a man who took up the game in college as a means of smoothing business deals.

There are now 18 courses in the Trump Golf portfolio, one that, he says, “somebody” has described as “the greatest collection of golf courses, ever, in the history of golf”. 

Some of those who have played with him, like Alice Cooper and the former Sports Illustrated editor Mark Mulvoy, have their doubts about his registered three handicap, but Trump will still ably fulfil the most coveted networking session of them all – a round with the commander-in-chief. For all that, it would not be unfair to suggest that his interests lay in what golf could do for him, not the other way round.

Trump has spoken derisively of attempts to grow the game, saying it should remain “aspirational”. One of his biggest course projects, and certainly his most notorious, is the Trump International resort on the Balmedie estate near Aberdeen in Scotland.

After purchasing the land in 2006, Trump secured the support of Scotland’s then first minister, Alex Salmond, to override natural protection laws and develop over a unique network of sand dunes. He had promised 6,000 jobs in return, but all but about 150 have never materialised.

Instead, he became engaged in a running feud with Salmond and with residents about a string of broken promises, a series of attempts to revise his plans, with the latest rejected in December, and his objection to a nearby wind farm. He also became the subject of another coruscating documentary – Anthony Baxter’s You’ve Been Trumped, which recorded his attempts to put the and squeeze on a durable local populace.

For Trump, the jobs were probably never the point. Golf had given him access to a coveted elite, and the tacit approval that comes from being their host. He had also enjoyed a glimmer of the prestige the grand old game can bestow.

Trump’s other Scottish course, Trump Turnberry, was once pencilled in to stage The Open in 2020. Confirmation was expected from the sport’s guardian, The Royal & Ancient, some time in 2015. Then came the relaunch of his political career.

“When Mexico sends its people, they’re not sending their best,” he said, at a speech in New York in June 2015. “They’re not sending you. They’re not sending you. They’re sending people that have lots of problems, and they’re bringing those problems with us. They’re bringing drugs. They’re bringing crime. They’re rapists. And some, I assume, are good people.”

It was the start of a run for American office steeped deeper in offensive rhetoric than any in generations, and it would only get worse from there. Even for the golf community – rich in social and fiscal conservatives, boat-steadying defenders of the line between sport and politics – this was too much. 

The Open offer never came. This had been the chance not to preside over some lucrative, confected sideshow, but to hand the Claret Jug to the winner of one of sport’s oldest, most famous contests. For Trump, this was a crowning moment of recognition, snatched away.

He may or may not think about it now.