Who leaked Jon Gruden's emails? Report claims Roger Goodell, Dan Snyder, other NFL execs played role

Dan Snyder's fall as the owner of Washington Commanders cannot be attributed to just one moment. 

But one of the most pivotal points of his demise was when the Wall Street Journal published an article on Oct. 8, 2021, with emails between former Las Vegas Raiders head coach Jon Gruden and former Washington executive Bruce Allen that contained racist remarks toward then-NFLPA executive director DeMaurice Smith. Those emails, which were from Gruden's time as an analyst for ESPN in 2011, kickstarted a chain of events that began with Gruden's resignation/firing and sped up the process that eventually ended with Snyder selling the team.

If not for those emails being leaked, some believe Snyder might still own the Commanders, according to a report from ESPN's Don Van Natta Jr. and Seth Wickersham. Snyder had already been suspended by the NFL after multiple allegations of workplace misconduct and sexual harassment, but the emergence of the emails led to a congressional investigation into Snyder, the NFL and the Commanders.

"He was free and clear that October — he just had to wait out his suspension and let everything blow over," a source close to Snyder told ESPN. "A major miscalculation. Without the leaks, he might just have survived."

Snyder and Goodell are biggest suspects in email leak

There are a lot of prevailing theories around who leaked the emails, and why.

The most widespread is — ironically — Snyder himself. This has been speculated for a while, and another source told ESPN that Snyder believed Gruden's racist remarks would shift the spotlight off of the Commanders owner and onto the ex-coach and simultaneously deflect the workplace misconduct allegations onto Allen, the former team executive.

If this is true, it's just another attempt by Snyder to control his own punishment over the past three years. It also wouldn't have been the first time Snyder used personal correspondence by others to try to influence the league. His legal team reportedly prepared a "Blackmail PowerPoint" to undermine Beth Wilkinson's investigation into the Commanders and persuade NFL commissioner Roger Goodell to give Snyder a lesser suspension after the workplace misconduct allegations came to light.

From ESPN:

"What was presented was not a defense against any of Wilkinson's findings made against Snyder; it was a series of screenshots of potentially embarrassing emails and texts from several top league executives, including Goodell's top lieutenant, [NFL general counsel Jeff] 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."

Later, more emails emerged — this time between Allen and Pash — in a New York Times article which were reportedly the same as the ones in Snyder's "Blackmail Powerpoint." This appeared to be, once again, an attempt to push blame from Snyder onto Allen. Lawyers close to the league and to Gruden also told ESPN that the decision to leak the emails to the Journal and the Times instead of the Washington Post was a major indication that Snyder was behind it.

Gruden and Raiders team owner Mark Davis, meanwhile, believed that Goodell and top league executives were the main culprits. Gruden still has pending litigation against the league, while Davis reportedly said the timing of the leak “felt like a setup” after he met with Goodell, per ESPN. Davis was also reportedly angry that he was seemingly the last person to know about the existence of the emails after Goodell, Pash and Snyder and that he felt like a scapegoat for the underlying Snyder issue. 

"It's ridiculous the league thought they could cherry-pick emails from years ago, when I wasn't even a coach and try to end my career." Gruden told ESPN in a statement added. "At a minimum, I deserved the opportunity to respond and receive some due process."

Four owners also told ESPN — it's unclear if Davis was one of them — they believed Goodell personally contributed to the release of the emails. Other sources told ESPN that NFL executives at least approved of the leak. 

The investigation conducted by the United States House Committee for Oversight and Reform also included testimony from Allen and Lisa Friel, the NFL's senior vice president and special counsel for investigations, that the Commanders had leaked the emails.

Another possible suspect is Smith, who was the target of Gruden's racist remarks. A source told ESPN that Smith "bragged" about his role in the leak, which coincidentally came on the same day he was voted to keep his job. Lloyd Howell replaced Smith as the director of the NFLPA after 14 years on June 28.

Naturally, all parties either denied or declined to comment on these allegations.

We may never know exactly who leaked the emails. But the result of it had and likely will still have major ramifications around the league. For one, the Commanders have new ownership — a group led by hedge fund manager Josh Harris. Whatever comes of the Gruden lawsuit could also affect the league. The story isn't over yet, but one of the biggest players is certainly off the board now.

(Disclosure: Josh Harris is a co-founder of Apollo Global Management, which owns Yahoo, Inc. He left the private equity firm in 2022.)