How and why the Jon Gruden emails leaked: A timeline and theories

Jon Gruden resigned on Monday night from his position as head football coach of the Las Vegas Raiders following a meeting with team owner Mark Davis. The 58-year-old coach resigned after numerous offensive emails he sent from a personal email account from 2011-2018 were made public.

Gruden had six more years left on his $100 million contract at the time of his resignation. He has already been removed from the Tampa Bay Buccaneers’ Ring of Honor.

We will examine the timeline of how this took place and possible theories explaining the leaks that made his private emails public.

What made Jon Gruden so famous and well known?

Gruden was a very young coach in the NFL at a time when many coaches were older. He developed a reputation for being a prodigy. He was only 35 during his first season as an NFL head coach. Gruden helped turn longtime backup quarterback Rich Gannon into a Pro Bowler and league MVP. He coached the Raiders from 1998-2001, was traded to the Tampa Bay Buccaneers, led them to a Super Bowl win over the Raiders in his first year at Tampa Bay, and then was fired by the Bucs in 2009.

At the time Gruden was fired by Tampa Bay, he had a well-known reputation for being an offensive-minded coach. He had a strong and quirky personality, and was full of energy. He went into broadcasting and became a major NFL presence on ESPN, commentating on “Monday Night Football” from 2009-2017, hosting a QB camp draft program, and participating in draft coverage. He was enough of a personality where comedian Frank Caliendo made part of his living by doing an impression of Gruden.

$100 million man

All the while he was with ESPN, Gruden was the subject of constant rumors about whether he would return to coaching. He denied those rumors and remained at ESPN through the years, despite being much younger than a typical retirement age. He rebuffed several efforts by the Raiders to bring him back. However, he finally relented and was lured away by Mark Davis to become the Raiders’ head coach ahead of their move to Las Vegas, thanks to a high-profile 10-year, $100 million deal.

A swift ending following leaked emails

Gruden was only in his fourth season on the job when he resigned Monday. Numerous emails he sent from 2011-2018 were leaked and reported about by two media outlets: The Wall Street Journal and The New York Times.

The contents of the emails led to his resignation, stained his reputation, and likely cost him a chance of ever coaching/working in the NFL ever again.

The First Leak: Email About DeMaurice Smith’s lips

The contents of the first leaked email were published in a story by The Wall Street Journal’s Andrew Beaton on Friday, Oct. 8, 2021. Gruden originally sent the email in 2011, amid an NFL labor lockout, to Allen, a close friend and former coworker of Gruden. The email contained an insult from Gruden regarding the size of NFL Players Association Executive Director DeMaurice Smith’s lips.

“Dumboriss Smith has lips the size of michellin (sic) tires,” Gruden wrote in a 2011 email to Allen, as reported by the Wall Street Journal.

Gruden intentionally misspelled Smith’s name as an insult.

Smith said in comments to the Journal that Gruden was making a racial remark about him and that this was an example of the racism and challenges he faces as a black executive.

In the same article, Gruden denied that the comment had anything to do with race. Instead, he said the comment was his way of calling Smith a liar, since he uses the term “rubber lips” to describe someone he thinks is double-talking or lying. One of Gruden’s former players, Tim Brown, even backed up that account.

The NFL and the Raiders admonished Gruden in a statement. The NFL made clear that it would be the Raiders’ responsibility to handle the situation. Gruden was allowed to coach his team for their next game, which turned out to be a 20-9 home loss to the Chicago Bears. The loss was a disappointing performance from the Raiders, who were possibly distracted by the Gruden matter, and played much worse than they had all season.

The Second Leak: A gay slur and much more

The second batch of leaked Gruden emails were published on Monday evening, Oct. 11, 2011, by The New York Times’ Ken Belson and Katherine Rosman.

In these emails, Gruden ran the gamut of offending people. According to the Times, Gruden used a gay slur, called out the NFL for “forcing” the Rams to draft a gay player (Michael Sam in 2014), and criticized NFL Commissioner Roger Goodell, Smith, and many others.

“In several instances, Gruden used a homophobic slur to refer to Goodell and offensive language to describe some N.F.L. owners, coaches and journalists who cover the league,” the Times reported.

How did the NFL got a hold of Jon Gruden’s emails?

Gruden traded numerous emails with his buddy, Allen. Allen was with the Raiders when Gruden was their head coach, and he was the GM of the Buccaneers when Gruden was Tampa Bay’s head coach. From 2010-2019, Allen served in high-level positions with Washington, beginning with an executive VP/GM title, to team president.

Though Gruden was sending emails from a personal email account, he was corresponding with Allen on Allen’s work email. That made the emails work/business emails for Allen, even if Allen treated his work email carelessly like he was on his personal email.

The emails Gruden exchanged with Allen came up during a legal investigation into Washington’s workplace.

Why was Washington being investigated, and by whom?

The Washington Football Team hired lawyer Beth Wilkinson in 2020 to investigate the team’s workplace and culture following several allegations of sexual harassment and verbal abuse.

In July 2020, The Washington Post published a story containing allegations from 15 women who were current or former Washington employees. The women shared accusations of sexual harassment they experienced while working for the team. Five former Washington employees, who as of the report’s publishing in 2020 were no longer with the team, were accused of sexual harassment and verbal abuse.

Also, in August 2020, The Post reported that Washington executives would watch a specially-created video of outtakes involving Washington cheerleader photoshoots.

Following these reports, Washington was pressured to act. Team owner Daniel Snyder then hired lawyer Wilkinson to conduct an investigation. The NFL later took over the investigation.

No written report of the investigation’s findings were ever made public.

Via WUSA9:

“The league said Wilkinson interviewed more than 150 people, including current and former employees. (NFL special counsel for investigations Lisa) Friel said individual allegations were not made part of Wilkinson’s findings because of confidentiality agreements requested by many people and that there was no written report, only an oral presentation.”

The franchise was fined $10 million, they hired and/or promoted several minorities, and Daniel Snyder stepped aside from running day-to-day activities to allow his wife to take over. But the Snyders were allowed to maintain ownership of the team.

The NFL did not make findings of the Washington investigation public and no written report was produced. That left many to wonder how and why only the emails sent by Gruden leaked out.

Timing of the Leaks

There are two theories/explanations at play regarding the timing of the leaks.

Theory 1: Keep Smith in office

It just so happens that Smith was facing a vote for reelection to his position as Executive Director of the NFLPA on the same day the first story was published regarding the email leak. A story published by ESPN on Oct. 6 reported that the NFLPA’s executive committee was split 7-7 on keeping Smith. The article said that Smith’s job was in jeopardy.

Some have theorized that the email was leaked and the publishing of the story was strategically timed to aid Smith’s reelection efforts. The theories suggest that such an email leak could paint Smith as a victim and appeal to the players on the basis of race.

Whether or not the leak had anything to do with it, Smith was ultimately reelected by the NFLPA. Maybe someone with the NFL, who wanted Smith to remain in his position because Smith works well with the NFL, leaked the news, and Gruden was collateral damage. We don’t know.

Theory 2: When Goodell saw the emails

If you don’t subscribe to theory 1, then you might believe that the timing of the leaks had to do with when the emails were reportedly presented to Goodell. Both the Wall Street Journal and New York Times articles said that the NFL reviewed more than 650,000 emails at Goodell’s direction and presented a summary to the commissioner early last week.

From the Journal:

Over the past few months, the NFL said, senior NFL executives have reviewed more than 650,000 emails, including this one, at commissioner Roger Goodell ‘s direction. Earlier this week, the executives presented a summary of that review to Goodell. The league added that it is sharing emails pertaining to Gruden with the Raiders.

Given that timeline, one could argue that the email leaked to the Journal because it was fresh material Goodell had just received, and the Journal published a story on it a few days later.

Maybe the timing was coincidental regarding Smith, and the person who leaked the emails thought that the lips comment about Smith was the most problematic of the Gruden emails. Perhaps the leaker thought leaking that comment would be enough to get Gruden fired, while sparing Gruden from having more problematic emails leak.

When no discipline was taken against Gruden, perhaps the leaker leaked more to force the Raiders to act.

“Clearly there were people affiliated with the National Football League and in the National Football League offices who wanted action taken, and they felt it should have been taken long before Monday night,” Adam Schefter reported on ESPN Monday night.

Pro Football Talk’s Mike Florio suggested the NFL leaked the first Gruden email.