Why The Jon Gruden vs. The NFL Case Is Such A Bigger Deal Than People Realize: Portnoy’s Guy Just Got the Green Light To Torch Goodell

NYT - Jon Gruden won a battle in his ongoing lawsuit against the NFL and commissioner Roger Goodell on Monday, with the Nevada Supreme Court upholding a ruling that denied a motion to send Gruden’s complaint into the league’s arbitration process.

With a 5-2 majority decision, the court not only confirmed the previous district court ruling but also reversed a May 2024 decision by a Nevada Supreme Court panel that would allow arbitration.

On Tuesday, NFL spokesperson Brian McCarthy told The Athletic that the league will appeal the decision and request a rehearing before the Nevada Supreme Court.

The next step following Monday’s decision was for Gruden’s case to move forward in public instead of going to arbitration, unless the NFL appealed.

In a statement by the majority Monday, the court said the NFL Constitution’s arbitration clause “does not apply to Gruden” because he was a former employee at the time his lawsuit was filed, calling its use in this case “unconscionable.”

“By its own unambiguous language, the NFL Constitution no longer applies to Gruden,” the statement read.

The court also refused an argument that arbitration language in Gruden’s contract with the Raiders would prevent him from suing the NFL. “The presence of an arbitration clause does not bind a party to arbitrate any claim, with any other party, at any time,” the court said.

Ok. I'm going to attempt to explain to the best of my law school dropout brain is capable of, just how, and why, everybody who's a fan of football, and/or hates Roger Goodell and the bullshit the league gets away with, should be so concerned about the latest ruling the Nevada Supreme Court recently upheld. 

Jon Gruden just scored the upset of the year in court, and I'm not sure anybody realizes it. 

The Nevada Supreme Court ruled that his lawsuit against the NFL doesn’t have to vanish into Roger Goodell’s arbitration dungeon like everything else the league "self-investigates". No buddy, it’s going forward in public. That’s a monster W for Gruden and a nightmare for the league office.

Because now comes the one thing the NFL never wanted- discovery.

To really understand how we got here, you have to rewind to 2021 and the absolute clown show that was Dan Snyder’s Washington Commanders investigation.

Yah, remember these?

The league had launched a “workplace culture” review of Snyder’s franchise after years of allegations about sexual harassment, toxic leadership, and the infamous “cheerleader scandal.” Lawyers got their hands on an insane 650,000 emails connected to Snyder and his organization.

Buried in that mountain of dirt were Jon Gruden’s old emails to Snyder and Bruce Allen. Gruden wasn’t even coaching at the time, he was working for ESPN. 

Those messages, sent between 2011–2018, contained a lot of bad language Gruden regrets. They were indefensible but they were sent privately between friends and never meant to see the light of day. But instead of treating them as part of a much larger web of dirt, the NFL conveniently leaked a handful (count, 11) to the media and turned Gruden into the story.

The league had 650,000 emails from the Washington Commanders investigation. 

Out of all that, they conveniently leaked only a dozen of Gruden’s to the media. Ugly stuff that torpedoed his career instantly. He resigned from the Raiders, was branded toxic, and ESPN/NFL pretended they never knew him.

Overnight, Gruden became the fall guy. 

The outrage machine locked on him, the Raiders cut ties, ESPN distanced itself, and the league washed its hands. 

But that was the point. He was the distraction. A sacrificial lamb to take the heat off the owners and the league itself.

But my oh my, how the tables have turned. Now, the rabbit has the gun. And the NFL’s dirtiest secrets might finally spill.

Snyder and the owners of crouse skated. Per usual. Funny thing happens when your product generates the most revenue for every major network in this country. The investigation that began with a league owner's gross workplace culture ultimately led to a coach losing his career.

That’s where the domino effect began. And that’s why Gruden sued, because he believes the league selectively leaked his emails to protect the billionaires at the top.

Now, as for why I think this is such a big deal? 

Because even a basic pre-law student knows that discovery = a death sentence. 

Don't believe me? Let's look at some recent and very pertinent history lessons. Because make no mistake, this isn’t the first time discovery has turned into an unholy mess for a sports league.

Deflategate. Remember that crock of horseshit?

The NFL just wanted to ding Brady for underinflated footballs because it had a masssssive CTE scandal ready to blow up its face, and a PR Agency advised the league's ownership cabal and Goodell that the only thing big enough to distract the public would be a scandal involving its biggest star. But I digress… 

Instead, once discovery and testimony started, the whole process exposed Goodell’s “I am the law” style justice system.

An absolute farce. Goodell declared himself judge, jury, and executioner, and everybody just had to deal with it.

Scientists, destroyed phones, ball boys with aliases like “The Deflator”, it became a complete clown show. Brady still ended up with four games, but the NFL’s credibility got dragged through the mud for years and took a way bigger hit than his legacy did.

And remember the MLB's "Steroid Hearings" on Capitol Hill?

Congress thought they were just hauling in McGwire and Sosa for some grandstanding. Instead, discovery and testimony cracked baseball wide open. Palmeiro lied under oath, Sosa “forgot how to speak English", and the Mitchell Report scorched half the league. MLB lost a generation of credibility, and Cooperstown is still dealing with the fallout. Absolute shit show.

The point is that once discovery starts, the people in charge lose control. And that’s exactly where the NFL is headed.

If you think Gruden’s emails were bad, just wait until lawyers start digging into the rest. For years, there have been whispers about Jerry Jones' blackmail stories that never saw print, and those could finally come to light. The Washington cheerleader scandal, already ugly on the surface, will probably look far, far worse considering how quickly the league dealt with that and tied up all the loose ends. 

There’s bound to be owner-to-owner dirt, because anyone who thinks Gruden was the only one firing off unfiltered messages is lying to themselves. 

Snyder was already caught hiding revenue from the league, and discovery could prove financial shadiness ran way, way deeper than anyone realized. 

The NFL’s media partners won’t come out looking clean either, since the cozy arrangements with ESPN and the networks could be laid out in black and white. And by black and white, I mean direct orders from the league to hang Gruden out to dry with their cherry-picked emails they so perfectly packaged and leaked out. 

And then there’s the unimaginable- the kind of stuff people wave off as conspiracy theory nonsense, right up until it’s sitting in a court document for the world to read.

And don't forget - when Gruden was radioactive, when ESPN and the league dumped him like he was toxic waste, Dave Portnoy gave him a platform. 

Barstool made him one of ours. 

Now Dave’s guy might be the one who torches the Shield. The same man they scapegoated could end up dragging Goodell and the owners through the mud, with their ugliest secrets spilling into public record. That isn’t just poetic justice, it’s a Barstool-certified fuck you to the league.

And I can't wait to see it unfold.

Because the NFL has truly been above the law and made a business of bending over anybody and everybody who dared cross them. Fuck, even when they didn't do anything wrong- like Brady, who is still the face of the league even when he's retired- they beat him like a dog that had gotten too comfortable just to show everybody else who's boss. 

So it really will be so sweet to witness if the dirt really drops, the fallout could be catastrophic. 

Owners could be forced to sell franchises if their names get tied to scandals, with Snyder remembered as only the appetizer. 

The league’s billion-dollar TV deals could suddenly get messy, because networks don’t love being in bed with a sport under Congressional investigation. Politicians would swarm, and hearings could drag the NFL through the same kind of public humiliation baseball endured during the steroid era. 

Goodell’s legacy, already hanging by a thread, would be torched once and for all; his “protector of the Shield” routine will justifiably be reduced to a punchline. 

Perhaps the worst, though, and one everybody should fear the most, involves the fact that people already joke about the league being scripted. But what if discovery proves manipulation and cover-ups are happening? Suddenly, the jokes stop, and the tinfoil hats become common sense. 

Of course, the NFL will stall, appeal, and unleash armies of lawyers to keep this buried. 

They’ll drag it through every court they can find, even the Supreme Court, in a desperate attempt to keep the lid on everything. 

But the fact that it’s even in public court is already a defeat for Goodell. Gruden may end up with a massive payday, but the real story is the dirt discovery that could be unleashed. The league wanted a fall guy. Instead, they may have handed Jon Gruden the dynamite to blow their empire wide open.