Jon Gruden was serving as the Oakland/Las Vegas Raiders’ head coach when the NFL told him to pack his bags and leave. The abrupt decision didn’t come overnight and stemmed from the coach’s problematic actions. But Gruden didn’t yield. Thinking he’s been dealt wrongfully, the former NFL leader hit the league with a lawsuit. And now, he’s due to stand his much-awaited trial, dating back to 2021.
Despite being out of the NFL scene since the same year, Jon Gruden hasn’t been able to move on properly, courtesy of his upcoming trial with the NFL. Last week, Clark County District Court Judge Hardy announced that the former head coach will be tried in the court in May 2027, and that the hearing could last for weeks. According to his latest announcement on Friday, many notable people from the NFL, including commissioner Roger Goodell, will be testifying. But the court document hasn’t assigned a date for the legal proceeding.
To rehash your memory, here’s what happened…
Former Las Vegas Raiders head coach Jon Gruden’s long-awaited trial against the NFL will begin next year. The case stems from leaked emails that led to his resignation. Read what happens next: https://t.co/eT6YaRxYkV pic.twitter.com/sXSaWT88Yd
— 8 News Now (@8NewsNow) March 30, 2026
The NFL reportedly forced Gruden to put his papers down on October 11, 2021. It stemmed from several emails (during a seven-year period ending in early 2018) to the Washington Football Team’s former president, Bruce Allen, and others dated 2011. Gruden, who was working for ESPN as a color analyst during “Monday Night Football” at the time, reportedly made racist comments against DeMaurice Smith, the former executive director of the NFL Players Association. The email was said to be discovered during a separate review of workplace misconduct at the Washington team after Goodell asked league executives to scan through over 650,000 emails.
Additionally, reports revealed Gruden used homophobic slurs several times to insult Goodell, while also calling him “clueless” and “anti-football.” In another instance, Gruden criticized the existence of women referees and the drafting of Michael Sam in 2014, the first openly gay player to be drafted by an NFL team.
When Gruden attempted to unmask the whistleblower, the NFL gave him the boot when the Raiders were 3-1. Soon after his “forced resignation,” Gruden filed a lawsuit against the NFL in a Nevada courtroom.
“I’m looking forward to having the truth come out, and I want to make sure what happened to me doesn’t happen to anyone else,” he said via ESPN. “What happened wasn’t right, and I’m glad the court didn’t let the NFL cover it up. The league’s actions disrupted the whole season. We were leading the division at the time, and they completely blindsided me and the team.”
In 2018, Oakland (now Las Vegas) signed him to a $100 million contract that would have run through 2027. However, the franchise didn’t pay him the remaining amount. Moreover, his lawyers claimed that the whole controversy slandered his image, resulting in the loss of brand deals, including one with footwear brand Skechers.
Meanwhile, the NFL has attempted to settle the case through arbitration and not a normal trial, fearing it would leak the whistleblower’s details and other business-related information. They even tried to discard the case under Nevada’s anti-SLAPP statute, a provision that protects whistleblowers under the First Amendment.
In December 2025, Judge Hardy shrugged off the NFL’s efforts and scheduled it for this year. After stepping away from the NFL, Jon Gruden returned to the spotlight in November 2024 through a multi-year deal with Barstool Sports to cover football content. As part of the partnership, he produces digital shows, including YouTube videos, his “Gruden’s QB Class.” Meanwhile, this wasn’t the only problematic report that came during his time with the Raiders.
Ex-NFL coach Jon Gruden reportedly painted pictures in bad light
Jon Gruden first joined the Raiders in 1998 and served as head coach for three years. He returned to take on the same role in 2018, but his second stint with the team wasn’t smooth. Known for being too meticulous in his draft approach, he relied heavily on the scouting department and pre-draft events to evaluate players up close. His roster decision often stemmed from his own vision for the team.
Even if a player has positive scouting reports, he would still lean on his own assessments. He would override suggestions and stick with his own decision even when his scouts invested significant time researching and endorsing a player. Basically, his influence within the organization made it difficult for alternative opinions to gain traction.
In addition to his uptight behavior, he reportedly opted for controversial tactics that involved creating so-called “kill tapes.” They were editing players’ clips to deliberately jeopardize a player’s prospects by only featuring his mistakes or weak moments. By focusing solely on flaws, these tapes could sway perception and undermine the more balanced evaluations provided by scouts.
“It wasn’t reflective of all the work you did,” an insider told Zak Keefer of The Athletic on condition of anonymity. “You can make a player look any way you want. You can make Tom Brady look like a bum.”
While some experienced scouts continued to stand by their assessments, many were reluctant to challenge Gruden’s stance. These especially included younger members of the staff. Ultimately, his authority and conviction often dictated the outcome. It showcased how much control he held over the Raiders’ draft decisions during that period.
