‘P.S. You Are A Loser’: That Time Donald Trump Sued The NFL And Got $3.76

When it comes to business prowess, Donald Trump is a classic case of a man whose legend (perpetuated mostly by his own self-aggrandizing) bears almost no resemblance to reality.

As you’re no doubt aware, there’s a very strong case to be made that Trump isn’t a good businessman at all. Between all the bankruptcies, lawsuits and first-hand accounts detailing a history of abject buffoonery, it’s pretty easy to come to the conclusion that Trump couldn’t negotiate his way out of a wet paper bag, let alone lay claim to some imaginary crown bestowed upon the world’s best dealmaker. Recall this hilarious assessment from Elizabeth Warren posted earlier this year:

Let’s be honest — Donald Trump is a loser. Count all his failed businesses. See how he kept his father’s empire afloat by cheating people with scams like Trump University and by using strategic corporate bankruptcy (excuse me, bankruptcies) to skip out on debt. Listen to the experts who’ve concluded he’s so bad at business that he might have more money today if he’d put his entire inheritance into an index fund and just left it alone.

That last bolded bit is particularly amusing as it suggests that in fact, Trump could have lived the very same jet-setting life of luxury and debauchery completely free from the stress and lawyer fees had he just entrusted his money to Jack Bogle. In other words: every buy and hold investor on the planet is a smarter “business”man than Donald Trump.

Recall that Trump and his businesses have been sued so many times that there is literally one lawsuit for every episode of every show ever produced about lawyers. Here’s the breakdown from John Oliver:

If each lawsuit involving Trump were the basis for an episode of Law & Order, they could sustain all 456 episodes of the original, all 389 episodes of Law & Order: Special Victims Unit, all 195 episodes of Law & Order: Criminal Intentand all 22 episodes of Law & Order: Los Angeles.”

As well as every episode of The Practice, Ally McBeal, LA Law, Boston Legal, Night Court, The Good Wife, Matlock, JAG, Perry Mason, Judging Amy, The Guardian, The Public Defender, Owen Marshal, Counselor at Law; Harry’s Law, Courthouse, Suits, Family Law, Sweet Justice, 1971’s The D.A., 2004’s The D.A., Reasonable Doubts, Damages, Shark, The Defenders, The Paper Chase, Head Cases, Judd for the Defense and all three episodes of NBC’s First Years.

And at that point you’re still missing one lawsuit. But you’ve also run out of television shows about lawyers. Meaning Trump’s lawsuits exceed the limits of the f*&$%ing genre!

The reason we bring this up is because we wanted to remind you about the time Donald Trump thought he was going to supplant the NFL.

The story of the USFL is long and winding, but here’s a brief history courtesy of a retrospective penned by Esquire last year:

So in 1983 [Trump] bought a football team, joining a confederacy of other rich rogues who had just completed their first season of the United States Football League. The business plan: compete with the NFL–sport’s one true, grim superpower, whom USFL owners mocked as the No Fun League–but not directly against it. The twelve-team USFL played its games in the spring, encouraged excessive end zone celebrations (the NFL penalized them), and allowed both replay challenges and two-point conversions after touchdowns (the NFL still didn’t permit either). Games were televised on ABC and an upstart cable channel called ESPN.

Trump purchased the New Jersey Generals from J. Walter Duncan, a laidback Oklahoma oil tycoon who got homesick travelling each weekend to watch his team play (“You weren’t going to outsmart him,” one observer said of Duncan. “But you might be able to out-talk him”). With Heisman Trophy winner Herschel Walker already in the backfield, the Generals had been the league’s flagship underachiever. They won just six games against opponents that stretched from Tampa Bay (whose halftime promotions included seven-car giveaways and the burning of mortgages) to Birmingham to Los Angeles, where the league eventually took over a team almost nobody came to watch. By the next season, when Trump bought in, the league swelled to eighteen cities–a money grab by owners to collect millions in franchise fees and soften their growing losses.

“He had so much enthusiasm, so much energy, so much positive-ness,” Steve Ehrhart, USFL executive director, told Esquire, recalling Trump’s cocksure attitude. “He said, ‘We’ve got to make this league as great as it can be. We’re going to take on everybody.'”

Sound familiar?

Ultimately, Trump pushed the rest of the league’s owners to try and move the USFL’s schedule from the spring to the fall, in order to “compete” with the NFL. They also decided to sue the league. Here’s what happened next, again, from Esquire:

The apocalypse arrived in the summer of 1986. Having already lost a collective $200 million, USFL owners, out-debated and out-maneuvered by Trump, voted 12-2 to move to a fall schedule. They also went ahead with a $1.7 billion anti-trust lawsuit against the NFL, who it claimed, among other things, had a chokehold on national TV rights. USFL owners hoped the suit would void the NFL’s TV contracts, force a merger, or provide a game-changing payday. So instead of playing football in the spring of 1986, the USFL landed in U.S. District Court in Manhattan. Ehrhart says Trump brought in lawyer Harvey Myerson–later jailed for a phony billing scheme–to lead the case. (Another of Trump’s lawyer pals, Roy Cohn, the commie-baiting counsel for Senator Joseph McCarthy’s hearings in the 1950s, served as only an infrequent consultant, says Ehrhart.) The NFL focused its defense on Trump. It portrayed him, Trump wrote in his 1987 bestseller The Art of the Deal, as a “vicious, greedy, Machiavellian billionaire, intent only on serving my selfish ends at everyone else’s expense.” To be fair, he’s been called worse.

The 42-day trial ended with a jury ruling in favor of the USFL. But it also concluded that the league’s dire straights were largely a result of its own doing, not the NFL’s, and so awarded the USFL damages totaling…$1. Damages in anti-trust cases are tripled, so the award grew to…$3. The USFL appealed all the way to the Supreme Court, which four years later allowed the award to stand. Including interest, the NFL stroked a check to the USFL for $3.76. Ehrhart still keeps it, uncashed, inside a Memphis bank’s safety deposit box. (Ehrhart also handled a $6 million check for the league’s attorneys’ fees and allows, “I did distribute that one.”)

Here is that check:

And believe it or not, that’s not the punchline.

No, the punchline comes from Mike Tollin (former head of the USFL’s highlight film show and director of ESPN’s 2009 documentary Small Potatoes: Who Killed the USFL?). Here’s how Tollin described Trump:

He was a bully. From the beginning I had enormous respect for [USFL commissioner Chet] Simmons and Bassett, and I saw him bullying them and using the USFL to get in the NFL through the back door. The NFL didn’t want him. Bassett was dying [from brain cancer], and Trump derailed Simmons. He was good at finding and exploiting an opponent’s weakness.

He’s the same guy who never lets the truth stand in the way of a good story or anything that furthers his ambition. He never lets humanity get in the way of personal gain. He’s the same guy who looks down on anyone in his way, whose audacity and narcissism knows no bounds.

Tollin sent Trump an advance copy of the documentary mentioned above on September 15, 2000.

Trump returned the letter with a personal note that ended with this:

P.S. YOU ARE A LOSER

Kinda gives you some perspective on the whole NFL debate, no?

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