What was supposed to be one of the NFL’s most exciting acquisitions quickly unraveled into one of its most infamous disasters. Antonio Brown, who started his NFL career with the Pittsburgh Steelers, grew disappointed with the franchise after nine seasons and requested a trade. That is when the Oakland Raiders’ then-coach Jon Gruden came into the picture, who roped in Brown. But what unfolded next left a detrimental impact on Gruden.

“I’ve kind of been trained my whole life to go get players that you covet, you cherish, you really want,” said Gruden on Not Just Football with Cam Heyward. “And every time I watched the Steelers practice in training camp, every time I saw him practice during the regular season, I was convinced if they didn’t have a fence around the stadium or the practice facility, Antonio would get killed by a car. He finished everything, man. I have not seen a guy practice that hard since Jerry Rice. I swear to God, I had to have 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, possibly on football, like he was in the past. But the two or three OTAs that we had him on the field, Cam, and he were running our routes, running my stuff… Holy sh*t, 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.”

Antonio Brown was likely to start for the Oakland Raiders in the 2019 season. He had HC Jon Gruden head over heels with his prowess. However, due to a series of controversies, the wide receiver never made his Raiders debut. It began with a frostbite incident. After using a cryotherapy machine in France without wearing proper protective footwear, Brown suffered frostbite and blisters on his feet that sidelined him from 10 out of 11 training camps.

Following that, Brown found himself in a banned-helmet controversy when the league didn’t allow him to wear a certain type of helmet. Eventually, he started missing practice sessions with Oakland, fueling the WR’s feud with the franchise.

Frustrated by his repeated absence, GM Mike Mayock fined Antonio Brown nearly $54,000. But Brown didn’t stay silent. He retaliated by posting the official fine letter on Instagram, publicly blasting the organization. Even though Brown offered a team apology, the Raiders fined him an additional $215,000 for conduct detrimental to the team.

Notably, this fine allowed the Raiders to legally void around $30 million in guaranteed money remaining on his contract. This attached clause seemingly disappointed Brown. As a result, he demanded his release on social media, and the Raiders officially cut ties with him hours later.