Jon Gruden wants to come back to the big leagues.  

Even though the former Oakland Raiders head coach has built a strong following online as a Barstool Sports host, Gruden expressed a desire to return to broadcasting. Looks like that wish has been granted.

“In about a month, Jon Gruden will be doing play-by-play on a [preseason] NFL game,” Ira Kaufman told 95.7 WDAE. “He’s not fooling around about this. He’s worked with Mike [Tirico], who’s about the best in the business. … I was talking to [Rich] Gannon, ‘Hey Rich, you think he’s going to get back into this? Does he want to be a head coach or something? 

“Gruden was working for Monday Night Football at the time. And, he told me that a big reason why Gruden was ready to leave Monday Night Football was he loved working with Tirico.”

Per FOX Sports’ Greg Aumann, Gruden is “expected to” be the play-by-play commentator for the Tampa Bay Buccaneers vs. Kansas City Chiefs preseason game on August 22 for WFLA.

Appearing on Ira Kaufman’s podcast right before this, Gruden said that he wants “to be play-by-play.” He cited the example of Frank Gifford, who had transitioned from a regular analyst into a play-by-play announcer. 

“I had nine years of watching these guys — [Mike] Tirico. And I’d like to give that a shot, man.”

Gruden worked with ESPN from 2008 to 2019 and has been working with Barstool since 2024. After nine years with ESPN as a broadcaster, he returned to a short-lived stint with the Raiders in 2018. He was reportedly ESPN’s highest-paid on-air employee, per Awful Announcing.

However, it won’t be all that easy for Gruden.

Play-by-play is a much different job than being an analyst on Monday Night Football. Gruden would be the first point of contact for games, instead of simply talking about everything related to them from the comfort of a TV studio. 

“Honestly, I have no idea of Gruden would be a good play-by-play announcer, but if he’s really interested in doing it, I would imagine he’d put in the requisite work to learn how to properly call games,” hockey commentator Phil Giubileo shared on X.

Gruden was still known for his energetic vibe on the MNF panel and was particularly renowned for the ‘Gruden Grinder’ segment. This was a special something he liked to felicitate players with each week – only those who had impressed him.

However, Gruden won’t exactly be coming back with a clean slate.

Jon Gruden set to face the NFL in court

Jon Gruden’s messy exit from the Raiders in 2021 often pops up in public memory. The former coach unceremoniously stepped down from his position after he was named in a league investigation into the Washington Commanders’ workplace culture. It found that Gruden had sent many incriminating emails to Bruce Allen, the team’s former general manager, making insensitive comments about some figures. He resigned after the contents of those emails were published by the New York Times.

Gruden sued the NFL in 2023, alleging that the controversy was a “malicious and orchestrated campaign” against him. He is seeking $150 million in compensation from the league. The latter was also denied a bid to settle this case in arbitration, since Goodell, the very person the former head coach was suing, would be the arbitrator.

The NFL tried to dismiss the lawsuit in 2025 after it was sent back to the District Court from the Nevada Supreme Court. However, a trial date has been set for May 2027, FOX 5 reported.