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Christian D'Andrea

10 things we learned about Dan Snyder’s awfulness from ESPN’s report on the Jon Gruden email leaks

I’d like to believe this is our last chronicle of all the awful and stupid things Washington Commanders owner Dan Snyder has done. In my heart, I know it won’t be.

Ostensibly, this is a breakdown of the latest reported transgressions from ESPN’s reporting of the ongoing strip mining of toxic sludge that has permeated every layer of Snyder’s franchise. It’s a recounting of the leaked emails that cost Jon Gruden his job as head coach of a totally different team and how Snyder’s alleged impatience eventually led to his own ousting after a series of passive not-technically-threats to NFL owners and officials. In short, emails discovered during a joint investigation into Washington’s toxic work environment — specifically, emails Gruden wrote using racist and homophobic language — were leaked to the press and had a still-catalyzing reaction.

There’s a lot of good stuff in there as well, from petty personal grudges to a shrugging game of “not me” among millionaires to, delightfully, Sean Payton calling Gruden a “dumb[expletive]” for paying league fines. This was never going to be a pleasant story, but at least with the worst person in the NFL finally, probably, on his way out, there was a silver lining.

But while Snyder’s alleged role in the leaks forced him into the imminent sale of the franchise he quickly smothered — a sale that will bring him more than $6 billion after buying the team for $750 million — it seems a given that the loudest braying jackass in a pasture made specifically for similarly minded animals won’t go quietly into his good night. Snyder may not own his team after 2024, (or maybe he will, it’s Dan Snyder, neither common sense nor sound logic play a role here). Either way, his truly depressing incapacity to learn from mistakes or better himself in any way makes it a near certainty that we will, sometime in the future, once again require a digest of all the terrible things he’s done.

This is probably just another volume in the encyclopedia of Snyder disasters. Let’s trace the story from its origin — amazingly, as always, reported by Seth Wickersham and Don Van Natta Jr. — and figure out whose lives Dan Snyder ruined this time.

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1
No one has owned up to the leaks, but most people believe it was someone in Snyder's camp

Tim Heitman-USA TODAY Sports

Every party who had access to the leaked emails has publicly denied any role in leaking them. The outlets that published them, citing policy, refuse to burn their sources. But the evidence suggests Snyder, or someone working on his behalf, was behind it, perhaps with the involvement of NFL partner Roc Nation and CEO Desiree Perez.

This theory takes on weight when you consider the emails were disseminated among journalists who’d covered Roc Nation or written pro-Snyder (or, at the very least, neutral) accounts of the team’s leadership in recent years.

Via ESPN:

Gruden’s legal team went as far as to research prior work by the reporters who received the leaks and found what it saw as favorable stories previously written about Dan and Tanya Snyder and Roc Nation. The Times’ Rosman wrote a piece in February 2020 about Roc Nation’s partnership with the NFL. The Journal’s Beaton wrote in June 2021 about Dan and Tanya Snyder’s efforts to reform the team’s culture, including a rare on-the-record interview with Dan Snyder. The Wall Street Journal declined to comment.

“How stupid can you be?” said a source close to Snyder who was aware of the previous stories done by the reporters who reported on the leaked emails. “They left a trail in the dirt.”

The reasoning behind leaking the emails? The short-sighted goal of giving Goodell a reason to oust a public rival in Gruden while helping advance the league’s efforts to stamp out racism at all levels. Instead, Goodell continued to freeze out Snyder and a congressional investigation into the leaks was announced days later.

2
Snyder's team low-key threatened the NFL by displaying texts and emails they believed incriminated the league

Rob Carr/Getty Images

In internal hearings to discuss attorney Beth Wilkinson’s investigation into the Commanders’ internal culture, Washington’s representatives took an unusual approach. Rather than defend their own decision making or attempt to limit the damage from then-president Bruce Allen’s email exchanges with Gruden, Snyder’s legal team instead displayed emails and texts from other league big wigs that looked like similar public relations disasters.

Snyder’s official argument was that the Commanders’ inner workings were no more toxic than the rest of the league’s, but the subtext was clear. Snyder had reportedly said for years he had dirt on other owners and executives throughout the league. Now he was presenting some of those receipts — receipts that looked a lot like the Gruden emails that would later go public.

More via ESPN:

When Snyder’s lawyers — famed defense attorney Joe Tacopina, assisted by Reed Smith partners Siev and James McCarroll — began to show a series of slides, those in the room were stunned …  it was a series of screenshots of potentially embarrassing emails and texts from several top league executives, including Goodell’s top lieutenant, Pash. The rationale, according to a source with firsthand knowledge, was to argue the hypocrisy of league officials judging Snyder. The tactics were so ruthless that some attorneys felt uncomfortable. Although none of the content was sexist, anti-gay or graphic, the signal was clear: If Goodell didn’t do what Snyder wanted in terms of handling the Wilkinson report and punishment, these emails and texts would be leaked.

It became known in league circles as the “Blackmail PowerPoint.”

3
As a result, Snyder got to help choose his own punishment like a spoiled teenager

(USA TODAY Sports Images)

The punishment meted out to Snyder was not standard for the NFL. Rather than a heavy hand, Goodell used a light touch and nebulous terms that made it seem like Snyder was hardly being held accountable. That’s reportedly because he was. The $10 million fine (donated to local nonprofits) and order to step away from publicly running the team — though he still attended home games — while his wife stepped into a leading role was a light punishment after a pattern of abusive behaviors so egregious the United States Congress eventually held an inquiry into it.

That’s because Snyder reportedly came up with the discipline himself. More via ESPN:

By late June, Snyder was “dictating his punishment” down to every detail, according to a source with knowledge of the deliberations. Legal sources said that Snyder and his lawyers were consulted by NFL executives in the drafting of the news release, with Snyder weighing in on word choices. It was an atypical and collaborative process, as compared with the way the league typically metes out punishment — notably in the one-sided judgments after Bountygate and Deflategate. Snyder and his team were pleased with the results, later bragging that the discipline was surprisingly light.

4
The original version of the Wilkinson report allegedly included a strong recommendation that Snyder sell his team

(Matthew Emmons-USA TODAY Sports)

These recommendations were never released to the public. The NFL contends no written document saying as much ever existed.

5
NFL executives and team owners believe Snyder would have survived the investigation into his toxic workplace had he simply served out his light league-mandated sentence

Mark J. Rebilas-USA TODAY Sports

Snyder remained banned from owners’ meetings, but still had the capacity to more or less conduct business as usual with the Commanders. Had he been able to accept this and bide his time before an eventual return, he may not have been pressured to sell his franchise (at least, not in any capacity that mattered).

Instead, Gruden’s emails went public and further alienated a man many of his fellow owners were happy to set adrift, leading to a potential sale and possible relief for long-suffering Washington fans.

ESPN later reported that Snyder’s lawyer, John Brownlee of Holland & Knight, believed that Snyder’s punishment was over as of Nov. 1, 2021. But Goodell refused to allow him back to league meetings. If Snyder could have lain low until the end of the season, owners and executives told ESPN, he might just have retained his team.

6
NFLPA executive director DeMaurice Smith, re-elected at the time the emails were leaked, bragged the leaks "worked"

AP Photo/Chris Carlson

The timing of these headlines coincided with an NFLPA election that threatened to cost Smith his job. This was seen as a risk for the league and its owners, as Smith is reportedly considered an uneven negotiator who has been on the hook for two collective bargaining agreements that failed to deliver what his players had been asking for. The leaked emails and Gruden’s alleged racist language may have helped swing a crucial vote to his side, keeping the executive director in power by a slim margin and giving NFL owners a sparring partner they knew was beatable.

From the ESPN report:

A lawyer who frequently works with the league said the timing of the leak was “suspicious because clearly it appeared to anyone paying attention that someone was trying to help De. Who had the incentive for De to keep his job? The NFL.”

Within hours of the Journal story, Smith was reelected as NFLPA executive director to a fifth term — by a single vote. Smith later bragged that the leak had worked, a source told ESPN.

7
The NFL's relationship with Roc Nation created internal strife at league headquarters

Harry How/Getty Images

Jay Z’s Roc Nation was brought in as a part in an effort to ease racial tensions within the league, particularly following Colin Kaepernick’s protests and then-president Donald Trump’s public criticism of both the protests and the league itself. That heavily publicized partnership gave Roc Nation the leverage to big time NFL officials.

More via ESPN:

Some in the league office believed Roc Nation had essentially appointed itself as the league’s marketing arm. And some league officials believed Roc Nation employees treated NFL staff dismissively, angering those who sincerely wanted to help find solutions to the league’s social justice problem…

“The NFL became afraid of Roc,” said a former NFL official, who adds that the partnership has been “a mess.”

8
Gruden, however, believes it was commissioner Roger Goodell who leaked the emails as part of a personal vendetta

Kelley L Cox-USA TODAY Sports

Gruden and Goodell have long had an adversarial relationship, dating back to his first stint as Raiders head coach. He saw the leaked emails as an endgame from his rival to chase him away from the NFL altogether.

Via ESPN:

“Why would these people want to come and get me?” The only explanation, [Gruden] said, is that he had led a leaguewide whispering campaign of “[expletive] Roger Goodell. And I’m not the only one, by the way. … Deep down, I knew he — Goodell — had me by the balls.”

9
Gruden also believes the Tuck Rule is evidence the league conspires against the Raiders

Ethan Miller/Getty Images

It’s not entirely germane to the Synder ousting — though it plants the seeds of Gruden’s angst against the NFL — and it’s a glorious detail. By this logic, the league inserted an obscure clause into its rule book years before, simply waiting for the right moment to spring it on the Raiders and give birth to the winningest quarterback in NFL history.

More via ESPN:

Davis often told Gruden that the executives at 345 Park Avenue played favorites — classic Raiders paranoia … How else to explain the since-eliminated Tuck Rule — a rule Gruden had never heard of before — that led to a Patriots playoff victory at the Raiders’ expense in 2002?

10
Sean Payton once phoned Gruden to call him a "dumb[expletive]" because he paid a $150,000 league fine

(Chuck Cook-USA TODAY Sports)

Gruden was docked a sixth round pick and fined $150,000 for violating league Covid-19 precautions in 2020. After he paid the bill, Payton — then still coach of the New Orleans Saints and who’d been put in a similar circumstance, called to bust him up about it. Per ESPN:

“I never paid the fine,” Payton told Gruden, adding that other coaches also refused to pay. “You’re the only dumb[expletive] that paid the fine.”

So, heads up new head coaches. You can just not pay those fines.

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