Jon Gruden isn’t coaching in the NFL anymore. Or, at least, not right now. He’s part of what he playfully refers to as the “Fired Football Coaches Association,” which isn’t a real institution at all.
Nevertheless, Gruden’s always grinding his gears about something, usually about football. He just can’t quit the game, even if he hasn’t been involved in the NFL since being a consultant with the New Orleans Saints in 2023.
Every now and then, Gruden pops back up in the NFL news cycle for one reason or another. This time, it’s for reflection purposes.
Super Bowl Ring in Hand, Jon Gruden’s Biggest Regret Is AB
While Gruden may or may not constantly be looking for a path back to being an NFL head coach again, he did have an excellent career. He didn’t have his first losing season until Year 6, just after he won Super Bowl XXXVII with the Tampa Bay Buccaneers.
Gruden even disappeared from the coaching picture for nine seasons, turning to broadcasting as a brief distraction. Once he re-emerged with the Raiders in 2018, Gruden returned with invigoration. It was time to do what no other head coach had ever done: win a Super Bowl with two different teams.
Except things didn’t go according to plan. One of the big swing and misses of Gruden’s tenure was trading for Antonio Brown. While the Raiders only parted with a third- and fifth-round pick for “AB,” it was a colossal failure. He never even played a game with them before being released from the roster.
Now, some seven years later, Gruden says Brown is still a player that sticks out in his coaching career. Once he saw how he trained, Brown was a player he just had to have.
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“I’ve kind of been trained my whole life to go get players you cherish, you covet, you really want,” Gruden said on Cam Heyward’s “Not Just Football” podcast. “Every time I watched the Steelers practice in training camp, every time I saw him practice during the regular season, I was convinced that (if) they didn’t have a fence around the stadium or practice facility, Antonio would get killed by a car.
“He finished everything. I have not seen a guy practice that hard since Jerry Rice. I had to have him.”
“It’s one of my biggest regrets of my career that that didn’t work out”@BarstoolGruden on acquiring Antonio Brown for the Raiders pic.twitter.com/k0Qe83Zaj6
— Not Just Football (@NotJustFootball) July 15, 2026
Gruden had a chance to watch Brown closely over the years while working with ESPN, traveling for Monday Night Football games. Eventually, Gruden got a chance to coach him, but again, things didn’t go according to plan.
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Now, the former coach says that not finding a way to make things work with Brown is one of the biggest regrets of his NFL career.
“We took a shot; unfortunately, it didn’t work out,” Gruden said. “The two or three OTAs that we had him on the field, and he was running our routes, running my stuff, I went home one night and opened a bottle of Asti Spumante and drank it all.
“I thought we were gonna complete every pass. I mean this guy’s running my routes better than they’ve ever been run before. It’s one of my biggest regrets honestly in my career that that didn’t work out.”
Brown’s NFL career didn’t last much longer after his failed stint with Gruden’s Raiders. He did, however, manage to win a Super Bowl alongside Tom Brady and the Tampa Bay Buccaneers at the end of the 2020 season. But after playing in seven more games in 2021, Brown’s football career was over, but not before he left a lasting impression on many of his former coaches and teammates.
