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The Jon Gruden saga over derogatory emails he allegedly sent while he was an ESPN broadcaster took an interesting twist this week with the NFL suggesting the former head coach also sent similar messages while he was with the Las Vegas Raiders.

The NFL said in court filings last week that Gruden sent similar emails while he was with the Raiders, and the messages weren't limited to the time he was a broadcaster and not on an NFL sideline, according to multiple reports.

"Gruden even claims in his Proposed Order that it is 'undisputed that all of Gruden's conduct referenced by the NFL Parties occurred prior to the signing of the Agreement and while Gruden was not an employee of the Raiders or the NFL,’" the league’s lawyers wrote.

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Roger Goodell at a news conference

NFL Commissioner Roger Goodell speaks at a news conference Feb. 9, 2022, in Inglewood, Calif.  (AP Photo/Morry Gash)

"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. 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."

Gruden's lawyer, Adam Hosmer-Henner, responded to the latest filings.

"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," Hosmer-Henner said 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?"

Jon Gruden coaching Raiders

Jon Gruden  (AP Photo/John Hefti, File)

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Gruden and the Raiders parted ways in October after misogynistic and racist emails were leaked to The New York Times and Wall Street Journal. The leaked messages showed Gruden exchanged racist and misogynistic emails with then-Washington team president Bruce Allen while working for ESPN.

The NFL and the Washington Commanders have denied leaking emails.

Gruden subsequently filed a lawsuit against the NFL and Roger Goodell, seeking damages on seven different claims as well as punitive damages and lawyer fees.

Jon Gruden vs Steelers

Las Vegas Raiders head coach Jon Gruden on the sidelines against the Pittsburgh Steelers during the second quarter at Heinz Field in Pittsburgh Sept. 19, 2021. (Charles LeClaire/USA Today Sports)

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In January, the NFL asked a Nevada court to dismiss the lawsuit and called accusations the league leaked the emails "baseless" and "should be dismissed for failure to state a single viable cause of action."