When coach Jon Gruden joined the Las Vegas Raiders in his second stint, he made it very clear that the last word, particularly in the draft room, was his. He relied heavily on his own assessments and tended to ignore the scouting department’s comprehensive research when a player failed to conform to his image. Even strongly backed reports would become as light as air when they did not align with his instincts. As pointed out by The Athletic, that strategy occasionally had more of a calculated twist to it, with so-called “kill tapes” being made to focus on a potential’s plight-edited footage that casts doubt and alters internal perception. Through the exposure of errors and the narrowing of context, such clips could often have a transformative impact on the perception of a player in the organization.

Nevertheless, Gruden has never lacked in results in his career. He has performed in tough situations, on primetime stages, as well as postseason journeys, and on the pinnacle with a Super Bowl victory. But the difficulty before him now stands way out of the game. Almost five years after he resigned, he is still engaged in a legal tussle with the NFL, claiming that the league was directly involved in compelling him to resign in a concerted effort. Although the NFL has made numerous efforts to have the case dismissed or transferred to arbitration, the courts have not done this and have proceeded with the case.

“Judge schedules trial between Jon Gruden, NFL, for mid-2027,” Awful Announcing posted on X, highlighting that a Las Vegas judge has finally set a trial date in the long-running lawsuit between Jon Gruden and the NFL.

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Jon Gruden, who has been in the NFL for almost four decades, sued the league just days after he resigned from his position as Raiders head coach in 2021. He held the NFL responsible for what he called a “malicious and orchestrated campaign” that led to him losing his job.

It all started with his resignation in 2021 after a league investigation. The investigation into the Washington Football Team for workplace misconduct uncovered emails Gruden sent from 2011 to 2018 to former general manager Bruce Allen.

According to The New York Times, those emails showed Gruden using misogynistic and homophobic language. After the details became public, he stepped down from his role in 2021. Within a month, he filed a lawsuit against the league.

As the case has moved through the courts, a trial is now officially set for May 2027 in Las Vegas, according to a KLAS 8 report. Clark County District Court Judge Hardy scheduled the trial this past week. It is expected to last several weeks and could include testimony from major NFL figures, including commissioner Roger Goodell, although the exact timeline is still unclear.

The NFL has tried to dismiss the case or move it to arbitration instead of a civil trial, but Gruden has continued to win key rulings that keep the case moving forward. In December 2025, Judge Hardy denied several NFL motions to delay or dismiss the case, including one tied to Nevada’s anti-SLAPP law, according to a KLAS 8 report.

According to Pro Football Talk, he is seeking up to $150 million in damages.

In a Case Conference Report filed on February 4, Gruden’s lawyers said his losses go well beyond $150 million. They said the damages include loss of his job, lost future opportunities, lost contract value, lost sponsorships, reputational harm, and legal costs tied to the case. The Case Conference Report came after an early case conference that the NFL chose not to attend.

With the trial date now set and so much money involved, attention turns to what happens next. The NFL could try to appeal to the U.S. Supreme Court or look to settle the case privately with Gruden.

Jon Gruden vs. the NFL Case

Looking back at the email scandal, Jon Gruden faced major backlash after details came to light. In emails reported by The New York Times, the Raiders coach used misogynistic and homophobic language to talk about different people.

Because of the backlash, Gruden was removed from the Tampa Bay Buccaneers Ring of Honor, where he had been inducted in 2017, and he stepped down from his position.

Gruden built a notable coaching career highlighted by a Super Bowl XXXVII win and his place in the Tampa Bay Buccaneers Ring of Honor. Over his time as a head coach, he posted a record of 122–116.

Within a month of resigning, he sued the NFL, claiming the emails were leaked on purpose to get him fired. While the lawsuit is still going on, Gruden has slowly made his way back into the spotlight. He returned in late 2024 as an analyst with Barstool Sports.

Since then, he has been easing back into the football world. Tampa Bay has put him back in its Ring of Honor, he showed up at Baltimore Ravens training camp, and his name has come up in coaching rumors. Well-known voices like Stephen A. Smith and Josh Pate have also supported the idea of him returning to coaching.