Jon Gruden didn’t dance around it: his biggest Raiders regret is the one that never made it to kickoff. On the Not Just Football podcast with Pittsburgh Steelers star Cam Heyward, Gruden said the Antonio Brown trade saga is the one that still sticks with him.
“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.”
That deal, of course, never got close to the finish line. Brown never played a game in Oakland, and the Raiders wound up giving up only a third- and fifth-round pick in the process. The optics were ugly, and the organization had to deal with the fallout, but the price tag was still manageable compared with the kind of mess it could have become.
Gruden made it clear he was willing to live with the baggage because of what he thought Brown could do on the field. Asked about the helmet issue, the frozen feet incident and the hot air balloon story, he said none of it really changed how he viewed the receiver.
“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.”
Then came the part that sounded like the peak of Gruden’s optimism. He said the brief stretch of OTAs with Brown had him convinced the offense was about to hum.
“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.”
Gruden’s second Raiders run ended with a 22-31 record and no playoff appearances before he resigned in disgrace during the 2021 NFL season after the email scandal. Rich Bisaccia then took over as interim coach and led the team to the playoffs. But when Gruden looks back, the Brown deal is the one he can’t shake.
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