Jon Gruden Admits Antonio Brown's Raiders Collapse is His Biggest Regret

In 2019, the Pittsburgh Steelers made the difficult decision to trade away their star wide receiver. After dealing Martavis Bryant to the Oakland Raiders in 2018, they struck another trade with the franchise involving a Pittsburgh receiver. This time, it was All-Pro Antonio Brown.

Brown had demanded a trade out of Pittsburgh following a bizarre falling out with the organization. The Raiders sent the first pick of the third round to the Steelers, who used it to select Diontae Johnson. However, Brown never played a game for the Raiders. In another bizarre twist that marked the beginning of the end of his NFL career, the Raiders eventually released him. It's a move that then-head coach Jon Gruden recently admitted he regrets.

During an appearance on Cam Heyward's Not Just Football podcast, the topic came up. Gruden called it the biggest regret of his coaching career. Not because he made the trade, but because he couldn't make things work between Brown and the Raiders' front office. Brown got into a verbal confrontation with general manager Mike Mayock after repeatedly failing to report to practice. The Raiders then voided Brown's guaranteed money, prompting him to demand his release.

In the grand scheme of things, though, Gruden has little reason to regret anything other than making the trade in the first place. Brown's unraveling was not something he reasonably could have predicted.

Antonio Brown was a ticking time bomb

After the Steelers defeated the Kansas City Chiefs in the 2016 AFC Divisional Round, Brown went live on Facebook. The team had barely left the field and was still celebrating the victory when head coach Mike Tomlin addressed the locker room. Unaware he was being recorded, Tomlin had some choice words about the Steelers' next opponent, the New England Patriots. The video sparked widespread backlash, and Brown received a $10,000 fine. He then signed a record-setting contract for a wide receiver during the 2017 offseason.

Some believe that incident marked the beginning of Brown's dramatic downfall. However, the warning signs didn't become more apparent until the 2018 season, when Brown reportedly argued with quarterback Ben Roethlisberger during practice. Brown later skipped practice before Week 17, was benched for the regular-season finale, and left the stadium before the game. Even then, the saga still seemed manageable, and the Raiders decided to take a chance on him.

Gruden and the Raiders had no way of knowing Brown's 2019 offseason would include multiple lawsuits, the helmet dispute, the foot frostbite fiasco, and the confrontation with Mayock. Even more remarkable, those incidents still weren't the wildest moments of Brown's time in the NFL.

Gruden shouldn't regret not making the trade work

Ultimately, most of Antonio Brown's problems were self-inflicted. Gruden even tried to reach him, only for Brown to later leak the conversation publicly. As the old saying goes, you can lead a horse to water, but you can't make it drink. The Raiders gave Brown every opportunity to get back on track, but he simply didn't want to be there, even after the team rewarded him with a lucrative reworked contract.

Gruden praised Brown's work ethic, recalling what he observed when the Steelers practiced against his teams before he became the Raiders' head coach. He even called Brown the hardest worker he had seen since Jerry Rice. That's lofty praise. At one point, Brown appeared well on his way to building the kind of historic career that Rice enjoyed.

Instead, Brown is now remembered as one of the greatest "what ifs" in NFL history.

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This story was originally published July 16, 2026 at 1:00 PM.