Jon Gruden NFL lawsuit timeline: How the former Raiders coach has battled in court over leaked email scandal

The Nevada Supreme Court has sided with Jon Gruden nearly four years after the former Las Vegas Raiders coach sued the NFL and commissioner Roger Goodell over leaked emails. Monday's decision to block the case from going to arbitration means the NFL's constitution and bylaws arbitration clause "does not apply to Gruden as a former employee and is unconscionable."  

According to a report from The New York Times, the NFL found emails involving Gruden from 2010 through 2018 in which homophobic, transphobic and misogynistic language was used. Gruden ultimately resigned from his post in October 2021, not even four seasons into his 10-year deal with the franchise.

Gruden sued the NFL and Goodell the following month, indicating the league tried to smear his credibility and name through a "malicious and orchestrated campaign" that "sought to destroy the career and reputation" after leaking his confidential emails.

Timeline of disparaging emails

Gruden's email leak came to light during the NFL's investigation of the Washington Commanders' toxic workplace environment, which was flagged in 2021. After a one-year investigation, the U.S. House of Representatives' Oversight Committee has released a 79-page final report with its findings, which included testimony from former Commanders owner Dan Snyder and former Washington president Bruce Allen, who alleges the franchise was to blame for the leaked emails involving Gruden.

Gruden repeatedly used profane and misogynistic language in various email correspondence with Allen, who worked in Washington's front office for nearly a 10-year stretch beginning in 2010. In deposition with the committee, Allen testified that an NFL official told him the Commanders leaked the emails to reveal the franchise's hostile workplace environment.

Gruden, caught in the crossfire, eventually resigned. The Wall Street Journal published a report in 2021 revealing the first leaked email from Gruden to Allen, which was sent during the NFL's 2011 lockout. Gruden used racial tropes to describe former NFLPA executive director DeMaurice Smith within the email.

Gruden later said he "never had a racial thought" when describing Smith to Allen and "never meant for it to sound that bad" after the email was made public. Gruden's disparaging emails also featured insensitive remarks toward former Missouri edge rusher Michael Sam following the 2014 NFL Draft.

Sam was selected in the seventh round by the Los Angeles Rams and was the NFL's first openly gay player to be drafted.

CBS Sports reported at the time the league was "waiting on the Raiders to take action" and was prepared to "step in" if Las Vegas did not address the situation beyond public denouncement of Gruden's emails. Team owner Mark Davis said Gruden's words "were not what the Raiders stand for" and admonished the verbiage used.

Gruden later admitted he had sent other emails that did not paint Goodell and various NFL team owners in a positive light. He blamed much of his vulgar criticisms toward the league on the lockout and told ESPN he "was in a bad frame of mind at the time" of the emails.

The NFL collected more than 650,000 emails during its investigation into Washington's workplace and Gruden's lawsuit pointed to "no explanation or justification" on why his were the ones that were made public during the season.

Gruden's legal standing

The former Raiders coach waited until after his resignation to sue the NFL and commissioner. And that decision makes the NFL's "unambiguous language" of its constitution not stand in court, according to the Nevada Supreme Court's ruling this week.

Article VIII of the NFL constitution states that the commissioner has "full, complete and final authority to arbitrate any dispute involving a member or members in the League or any players or employees of the members of the League or any combination thereof that in the opinion of the Commissioner constitutes conduct detrimental to the best interests of the League or professional football."

The ruling, as obtained by Front Office Sports, noted the NFL's ability to amend its constitution at any time without any notice also renders the arbitration clause substantively unconscionable. The NFL has not commented on the Nevada Supreme Court's ruling.

Next career steps

Gruden has mostly stayed out of the public eye since his NFL resignation, but recently said he would love to return to coaching. Several anonymous college administrators acknowledged to CBS Sports last fall that while Gruden comes with baggage, there may be programs outside of the Power 5 willing to listen.

"The only reason I really came here is I want to coach again," Gruden said during a speaking engagement this month, hosted by the Georgia Bulldogs. "I'm being honest with you, I do not bullshit, either. I want to coach again. I'd die to coach in the SEC. I would love it. I would f---ing love it."

Gruden's last year in the college coaching ranks came at Pitt in 1991 as the Panthers' wide receivers coach. He later enjoyed assistant stints with the Packers and Eagles before accomplishing big-time success with Oakland and Tampa Bay. Gruden won his only career Super Bowl title with the Buccaneers to end the 2002 season and is a member of the franchise's Ring of Honor.