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NFL now claims Jon Gruden sent derogatory emails while serving as Raiders coach

As the Jon Gruden lawsuit continues to play out, NFL attorneys have revealed that he "consistently" sent "derogatory emails" while serving as the Raiders' head coach.

When it comes to keeping all legal claims in its secret, rigged kangaroo court, the NFL will go to great lengths. Usually, that means appealing to the highest courts in the land any and all rulings defeating the league’s effort to push cases to arbitration.

In the lawsuit filed against the NFL and Commissioner Roger Goodell by former Raiders coach Jon Gruden, the appeal process has yet to begin. The clock for filing an appeal won’t even start to run until a final, written order is entered regarding the ruling that the case should stay in court. And as the two sides haggle over what the formal document denying the NFL’s effort to compel arbitration should and shouldn’t say, the NFL has said something very significant.

Via David Charns of CBS 8 in Las Vegas, the league has suggested that Gruden’s potential habit of sending “derogatory” emails wasn’t confined to the over-the-top messages sent to former Washington executive Bruce Allen in 2011, when Gruden wasn’t employed by any NFL team.

In a court filing submitted last week, the NFL’s lawyers questioned the accuracy of the proposed order submitted by Gruden’s representatives. “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,” the league’s lawyers wrote. “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.”

This means that the league believes (or already knows) that Gruden sent problematic emails not only while he worked for no NFL team but also after he returned to the Raiders in 2018. Gruden’s lawyers argue that the league has blown its window to bolster a failed argument that the case should be resolved in arbitration by arguing that Gruden also sent “derogatory” emails after joining the Raiders.

“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 issued on Monday. “In fact, their own attorney conceded during the hearing that the emails were sent before Jon Gruden signed with the Raiders.”

In other words, it’s too late for the NFL to support the argument that the case should be sent to arbitration by pointing out that Gruden sent “derogatory” emails after returning to coach the Raiders. It’s possible that the NFL didn’t find the emails until after the court issued a verbal ruling in May that the case should not be sent to arbitration. It’s also possible, if not likely, that the league hopes to utilize this specific process to further smear Gruden in a semi-legitimate way.

Gruden lawsuit arises from the fact that someone leaked the emails he sent to Allen when Gruden was working for ESPN. If someone were to leak emails Gruden sent while working for the Raiders, a new lawsuit would be filed. (Or, at a minimum, the current lawsuit would be expanded.)

But this is part of the defense-lawyer playbook in civil cases. Even though Gruden’s ouster had nothing to do with any emails he sent while working for the Raiders, the scorched-earth effort to win the case (and to make him regret even bringing it) includes looking for anything that can be used to make him look bad. And if it can be shown that Gruden sent similarly problematic emails while working for the Raiders, that definitely would make him look bad.

If the case ends up in arbitration, chances are those emails will never see the light of day. If the case remains in court, those emails likely will become a cornerstone of the league’s defense, under the clunky title of “after-acquired evidence.”

The argument goes like this: After the plaintiff sued us, we started looking for any and all dirt that we could find. And here it is, our after-acquired evidence. More commonly known as “f--k around and find out.”