‘Little Awkward’ — NFL Insider Makes Feelings Clear on Jon Gruden’s Broadcasting Return Amid Lawsuit Against League

A return to the NFL seems to be in the near future for Jon Gruden. With more than a decade of coaching experience under his belt, he put together a strong resume with the Oakland / Las Vegas Raiders and the Tampa Bay Buccaneers.

However, after a scandal exposing his derogatory emails, he was forced to resign from the role in Las Vegas. Now that he’s returning as a broadcaster, one insider isn’t sure the entire scenario will come together smoothly without a hitch.

The Jon Gruden Broadcasting Return Isn’t Without Controversy

A spectacular career as head coach saw Gruden reach the AFC Championship Game in 2000 with the Raiders, though a shift to the Buccaneers ultimately led to him capturing the elusive Super Bowl.

Unfortunately, beyond that triumph, his tenure with the Buccaneers was underwhelming, at best, as the team returned to the postseason just twice. Then, going nine years without a head coaching role, he took over the role for the Raiders once again in 2018.”

His next tenure lasted just three full years with the franchise before he resigned early in the 2021 season. At the time, many racist, misogynistic, and homophobic emails allegedly sent by Gruden were exposed to the public.

Since then, he’s served as a consultant for the New Orleans Saints and an Advisor to Milano Seamen, but his primary role has turned to a career in sports media. Taking on a role at Barstool Sports in 2024, he remains involved with the company.

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But now, almost five years after his exit, Gruden is gearing up for a return to the league, this time in a broadcasting role for a preseason game as the play-by-play announcer. However, the idea might not go off as smoothly as it appears on paper.

Mike Florio of NBC Sports went into detail about the potential problems this partnership presents. Speaking on “Pro Football Talk,” he immediately jumped to the lawsuit the former Super Bowl champion has filed against the league.

“It does get a little awkward because Gruden’s got the lawsuit against the NFL and the commissioner for deliberately leaking supposedly secret documents from the Washington investigation that seemed to be leaked in a way that was aimed at taking him out during the 2021 season,” Florio said.

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It wasn’t a shot in the dark for Gruden, as he’s already become a beneficiary of a key ruling in his case against the NFL in August when the Nevada Supreme Court determined his case could proceed in court instead of arbitration. Florio, too, has problems with the way the league handled the situation.

“The biggest problem I continue to have with all of this is that taking him out five weeks into the season undermined the integrity of the season. They knew what they knew before the season started. They could have done it in June,” he claimed, when the reports first came out. “They didn’t do it then. They could have done it then, or they could have waited until after the 2021 season.”

Mentioning the Nevada case ruling, the veteran insider also explained how this could be the final step before Gruden returns to his coaching roots in the NFL.

“Through it all, Gruden’s getting hired by somebody,” Florio continued. “Either by a team, by a broadcast operation the team owns, or by a radio or TV affiliate that has a contractual relationship that could be terminated with an NFL team. So the fact that this is even happening, it’s just a stone’s throw from somebody hiring Jon Gruden to be a coach or an offensive coordinator.”

It remains to be seen if the next steps for Gruden will land him back in the NFL in a coaching capacity. But as he continues to build out of his career, while also finding success in the court case, it is becoming a situation that might be harder for the league to ignore.