Al Davis probably rolled over in his grave a few times when the Oakland Raiders announced in 2018 that they were hiring Jon Gruden to be their head coach on a 10-year, $100 million contract. After all, just a decade and a half prior, the team's larger-than-life owner had traded Gruden away.
And the results during Gruden 2.0 were the results. He resigned in disgrace partway through the 2021 NFL season after the infamous email scandal, finishing his second stint with a 22-31 record and no playoff appearances. Rich Bisaccia then led Gruden's team to the playoffs as the interim.
By all accounts, Gruden's reemergence in Oakland and Las Vegas was a disaster, headlined by several unsavory stories and developments. And it was only recently that fans learned just how much worse Gruden's second tenure was with the Silver and Black.
In his eyes, though, Gruden has one obvious regret about this time.
Former Raiders HC Jon Gruden regrets not getting to work with Antonio Brown
Gruden recently appeared on the Not Just Football podcast with Pittsburgh Steelers star Cam Heyward, who is the brother of current Raiders fullback Connor Heyward. There, Gruden revealed that the Antonio Brown trade not panning out was his biggest regret.
"It was a roll of the dice, let's not kid ourselves. There were some risks involved on both sides," Gruden admitted. "But again, I'll say this: it's one of my biggest regrets of never getting to coach him. ... We took a shot. Unfortunately, it didn't work out. There were some issues, I think, off the field that he wanted to deal with. He wasn't really as focused on football like he was in the past."
Now, in a lot of ways, the Raiders mitigated disaster in this deal. Sure, the optics of it were atrocious, and they had to mend the fences within the organization and rebuild the culture, but all they gave up was a third and a fifth-round pick. That's not too difficult a pill to swallow, all things considered.
Was it ideal? Absolutely not. And Las Vegas should have known that an all-time receiver being sold for that price was sure to come with some serious baggage. But it is quite clear that Gruden just fell in love with the talent that was Antonio Brown and thought success on the football field was a cure-all.
When asked about Brown's issues that offseason, namely the helmet problem, the frozen feet incident and the hot air balloon story, Gruden was pretty numb to all of it.
"I didn't even care. I'm okay with all of it. You know, I said, '[Expletive], you just get him to game day.' I kept telling my guys, 'We're just going to get him to Sunday. We're going to get this guy to Sunday,'" Gruden said. "There's certain players, and you know this, right or wrong, that have a little bit bigger yard to play in than others. I just wanted to get around this guy and try to build a relationship with him and bring him into our world a little bit, but he was, I think, distracted by other things. I can't speak for him, but none of that stuff really bothered me. Don't get me wrong, it concerned me quite a bit, but I saw what he did in these OTAs, and I just had to get him to Sunday for the Raider Nation. I just knew he could be spectacular in our offense. But what a disappointment for me."
He then recounted his favorite story about coming home from OTAs and believing that the Raiders' offense was going to be in rarified air that coming season.
"The two or three OTAs that we had him on the field, Cam, and he was running our routes, running my stuff, I went home one night, opened a bottle of Asti Spumante and drank it all. I thought we were going to complete every pass," Gruden recounted. "Holy [expletive], I mean, this guy's running my routes better than they've ever been run before. And it's one of my biggest regrets, honestly, in my career that that didn't work out."
Brown's numerous debacles in a short period with the Silver and Black, which ultimately led to him never playing a game in Oakland, are well-documented. We don't need to go back over them or re-live them. But it's painfully obvious that Gruden feels like this whole thing was his biggest regret.
It should be.
Add us as a preferred source on Google