Here is a look back at what led to Gruden's resignation in 2021 and the court cases that have followed.
Jon Gruden leaked emails timeline: Everything to know about head coach's controversial firing from Raiders originally appeared on The Sporting News
A major development has come in Jon Gruden's appeal against the NFL, as the Nevada Supreme Court has ruled in favor of the former head coach.
The news comes nearly four years after the NFL uncovered emails involving Gruden from 2010 through 2018 in which he used homophobic, transphobic and transphobic language, according to a report from The New York Times.
At the time, Gruden was the head coach of the Raiders, and in the wake of the news, he informed his team that he would resign from his position.
The new development means that Gruden will now have his day in court to prove allegations that his emails were improperly leaked by the NFL and its commissioner, Roger Goodell.
Here is a look back at what led to Gruden's resignation in 2021 and the court cases that have followed.
MORE: Why Jon Gruden resigned from Raiders job in 2021
Jon Gruden leaked emails timeline
Gruden's emails were uncovered as part of a workplace misconduct investigation into former Washington president Bruce Allen. In 2011, Gruden, who ESPN employed at the time, appeared to use a racist trope to describe former NFLPA executive director DeMaurice Smith.
After Gruden came under fire for his description of Smith, more disparaging emails from the probe were released to the public. Gruden's suits stemmed from the fact that his emails were leaked, out of over 650,000 emails found in an investigation into Allen.
MORE: What to know about Jon Gruden's new foray into sports media
First emails referencing former NFLPA chief DeMaurice Smith are leaked
On Oct. 8, 2021, the Wall Street Journal published a report outlining the first leaked email from Gruden that was sent to Allen.
During the NFL lockout in 2011, Gruden said Smith had "Dumboriss Smith has lips the size of michellin (sic) tires." Gruden apologized for the email, saying he routinely uses the term "rubber lips" to "refer to a guy I catch as lying ... he can't spit it out."
He added, "I'm ashamed I insulted De Smith. I never had a racial thought when I used it. ... I'm embarrassed by what's out there. I certainly never meant for it to sound that bad."
In response, an NFL spokesperson said, "The email from Jon Gruden denigrating DeMaurice Smith is appalling, abhorrent and wholly contrary to the NFL's values. We condemn the statement and regret any harm that its publication may inflict on Mr. Smith or anyone else."
Raiders owner Mark Davis said the contents of the email were "not what the Raiders stand for."
In response to being mentioned, Smith told the Wall Street Journal that, "This is not the first racist comment that I've heard and it probably will not be the last. This is a thick-skin job for someone with dark skin, just like it always has been for many people who look like me and work in corporate America."
Gruden admits 2011 emails also include language that disparages Roger Goodell
Two days after the initial leak, Gruden confirmed that he had sent emails disparaging the NFL commissioner and team owners with obscene language.
"I was in a bad frame of mind at the time [during the NFL lockout], and I called Roger Goodell a [expletive] in one of these emails too," Gruden told ESPN.
Gruden resigns as Raiders head coach after the contents of other emails are leaked
After the initial leaks, the New York Times detailed Gruden's emails that contained homophobic and misogynistic language on Monday, Oct. 11. Gruden resigned as Las Vegas' head coach hours after the detailed report.
"I have resigned as Head Coach of the Las Vegas Raiders. I love the Raiders and do not want to be a distraction. Thank you to all the players, coaches, staff, and fans of Raider Nation. I’m sorry, I never meant to hurt anyone."
— Las Vegas Raiders (@Raiders) October 12, 2021
Jon Gruden
In the final round of emails leaked by the New York Times, Gruden used a homophobic slur about Goodell, also calling the commissioner a "clueless anti-football p—."
The emails were found to span from 2011 to 2018, and also included insensitive language about the Rams' 2014 draft selection of Michael Sam, the first openly gay player in NFL history.
Within 15 minutes of Gruden's announcement, Davis shared a statement accepting the head coach's resignation.
— Las Vegas Raiders (@Raiders) October 12, 2021
MORE: Inside the Buccaneers' decision to reinstate Jon Gruden into franchise's Ring of Honor
Gruden sues NFL, Goodell for their roles in releasing emails
A month after his resignation, Gruden filed a lawsuit against the NFL.
"Through a malicious and orchestrated campaign, the NFL and Commissioner Roger Goodell sought to destroy the career and reputation of Jon Gruden," the lawsuit read in part. "When their initial salvo did not result in Gruden's firing or resignation, Defendants ratcheted up the pressure by intimating that further documents would become public if Gruden was not fired."
The suit also questions why Gruden's emails were made public and the timing of their release.
"There was no explanation or justification for why Gruden's emails were made public out of the 650,000 emails collected in the NFL's investigation of the Washington Football Team or why the emails were held for months before being released in the middle of the Raiders' season."
The NFL and Gruden trade wins in court
The lawsuit has had multiple stages, with Gruden first getting a win as a lower-level state judge rejected the NFL's attempt to dismiss the lawsuit or force it into private arbitration overseen by Goodell.
In May 2024, the Nevada Supreme Court ruled in the NFL's favor with a 2-1 vote to dismiss the case. Gruden's lawyer, Adam Hosmer-Henner, called the decision "outrageous and unconscionable," and shared that he would look for the case to be heard by the full court.
Five months later, however, the Nevada Supreme Court granted Gruden's motion for the case to be heard by the full court.
Full Nevada Supreme Court rules in Gruden's favor
On Aug. 11, 2025, the Nevada Supreme Court reached a 5-2 ruling that sided with Gruden in his lawsuit.
The justices did not determine whether or not the NFL had leaked the emails, but they did find the league's decision to force the complaint into arbitration proceedings overseen by Goodell was "unconscionable," as reported by ESPN's Don Van Natta Jr.
Because Gruden was no longer an NFL employee, he should not have been subject to mandates outlined in the league's constitution.
"By its own unambiguous language, the NFL Constitution no longer applies to Gruden," the justices wrote. "If the NFL Constitution were to bind former employees, the Commissioner could essentially pick and choose which disputes to arbitrate."
"We're very pleased with the Nevada Supreme Court's decision, not just for Coach Gruden but for all employees facing an employer's unfair arbitration process," Hosmer-Henner said on Aug. 11. "This victory further vindicates Coach Gruden's reputation, and it clears the way to swiftly bringing him full justice and holding the NFL accountable."
The NFL declined to comment.
Category: Football
