LAS VEGAS (KLAS) — Lawyers for the National Football League claim former Las Vegas Raiders head coach Jon Gruden “consistently” sent “derogatory emails” while he led the team, court filings the 8 News Now I-Team reviewed Monday indicate.

Gruden filed the lawsuit against the NFL and its commissioner, Roger Goodell, in November 2021, over what he called his “forced” resignation the month before. Recent court filings debate whether the issue should be settled in court or through arbitration.

Gruden resigned from the Raiders on Oct. 11, 2021, after emails surfaced showing he used racist, misogynistic and homophobic comments. A New York Times investigation revealed Gruden had not only used racist comments in an email in 2011, but had regularly used derogatory language in emails during his employment with ESPN.

The report specifically noted that for several years, Gruden “casually and frequently unleashed misogynist and homophobic language… to denigrate people around the game and to mock some of the league’s momentous changes.”

Jon Gruden, center, appears in court Wednesday, May 25, 2022, in Las Vegas. A Nevada judge heard a bid Wednesday by the National Football League to dismiss former Las Vegas Raiders coach Jon Gruden’s lawsuit accusing the league of a “malicious and orchestrated campaign” including the leaking of offensive emails ahead of his resignation last October. (AP Photo/John Locher)

Lawyers for the NFL and Goodell write in court documents filed last week that Gruden was a league employee during the time when some emails were reportedly sent, indicating their push to settle the lawsuit through arbitration.

“In several places, Gruden’s proposed order states that the emails were ‘sent between 2011 and 2018, during which time Gruden was not working as a coach in the NFL but as an employee of ESPN,” lawyers for the NFL and Goodell said in a filing last week.

“Gruden’s claim (and purported finding of fact) on the timing of his emails is, in reality, very much disputed by the NFL parties and in fact false,” lawyers for the NFL write. “Discovery — necessary to make any finding of fact on this issue — will show that Gruden continued to send the same kinds of derogatory emails consistently following his start date with the Raiders.”

The filing does not contain any documentation for the claim.

FILE – In this Jan. 29, 2020, file photo, NFL Commissioner Roger Goodell smiles before answering a question during a news conference for the NFL Super Bowl 54 football game in Miami. Goodell has sent a letter to fans outlining the league’s plans to play during the coronavirus pandemic. As veterans begin reporting to training camps this week, Goodell noted Monday, July 27, 2020, how COVID-19 has “turned the world upside down.” (AP Photo/David J. Phillip, File)

“The NFL did not make these unsubstantiated arguments in the motions they already lost and will not be able to make them if they appeal,” Gruden’s attorney, Adam Hosmer-Henner, said in a statement Monday. “In fact, their own attorney conceded during the hearing that the emails were sent before Jon Gruden signed with the Raiders. The NFL has tried to avoid discovery from the start, not Jon Gruden. This is just another attempt by the NFL and Commissioner Goodell to save face by attacking Jon Gruden while still not owning up the truth of their actions. Jon isn’t going to try to hide from his deposition, is the commissioner?”

Gruden’s comments came under fire last fall after the first email was made public and revealed Gruden wrote emails complaining about then-head of the NFL’s Players Association, DeMaurice Smith, who is Black, to Bruce Allen, then with the Washington Football Team, that “Dumboriss Smith has lips the size of Michelin tires.”

“The complaint alleges that the defendants selectively leaked Gruden’s private correspondence to the Wall Street Journal and New York Times in order to harm Gruden’s reputation and force him out of his job,” Hosmer-Henner said in a statement to the I-Team last year. “There is no explanation or justification for why Gruden’s emails were the only ones made public out of the 650,000 emails collected in the NFL’s investigation of the Washington Football Team or for why the emails were held for months before being released in the middle of the Raiders’ season.”

Recent court filings indicate the NFL completed its investigation into alleged harassment in the Washington organization in July 2021.

Gruden and the NFL agreed to a confidential settlement when he resigned, court documents indicate.

Gruden signed a $100 million contract with the then-Oakland Raiders in 2018. According to the lawsuit, he is not being paid the remaining balance on the contract, which runs through 2027. His lawyers also write Gruden is losing out on endorsement deals, including one with footwear company Skechers.

Gruden’s lawsuit seeks a jury to award Gruden damages for his resignation.

In May, a judge declined the NFL’s request to throw out the lawsuit. Gruden left court that day saying, “Go Raiders.”

The 8 News Now I-Team first reported the news Monday.