When Jon Gruden joined the Las Vegas Raiders for his second stint, there was a lot of hype. Things got off to a rough start with the surprise Khalil Mack trade and the team only winning four games in his first season, but it was looking a lot more exciting heading into Year 2.
The team swung a trade with the Pittsburgh Steelers for Antonio Brown, who was widely considered the best wide receiver in football at the time. Unfortunately, he never ended up playing a game.
That was a massive disappointment for Gruden, who recently said that Brown not working out with the team was one of the great regrets of his career.
“I didn’t even care. I’m OK with all of it,” Gruden said on Cam Heyward’s “Not Just Football” podcast. “I said, ‘(Expletive), just get him to game day.’ I kept telling my guys, ‘We’re just gonna get him to Sunday. We’re gonna get this guy to Sunday.’ There are 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.
“None of that stuff really bothered me. Don’t get me wrong, it concerned me quite a bit. 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.”
Gruden Thought Raiders Would Complete Every Pass
Brown was meant to be the centerpiece of the Raiders’ offense that season. The team also added Tyrell Williams to give him a solid No. 2, and had an emerging Darren Waller at tight end.
The Raiders went 7-9 that season, but Brown’s presence could’ve changed things. Gruden was so excited before they cut the wide receiver that he even celebrated prematurely.
“The two or three OTAs that we had him on the field, and he was running our routes, running my stuff,” Gruden said. “I went home one night, opened a bottle of Asti Spumante and drank it all. I thought we were going to complete every pass.”
Among Gruden’s Biggest Regrets
The 2019 Raiders are one of the great “what-ifs” in franchise history. Now, they likely didn’t have enough to compete for a Super Bowl that year, but they could’ve been in the mix for the playoffs.
Plus, he was on a three-year contract, so who knows how good the team could’ve been. It still haunts Gruden that he didn’t get to coach Brown.
“It’s one of my biggest regrets, honestly, in my career that that didn’t work out. … It’s one of my biggest regrets, of never getting to coach him,” Gruden said.
For his part, Brown didn’t last much longer in the NFL. He played 16 more games across three seasons until teams decided he was too toxic to work with. He hasn’t played since 2021.
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