Gruden also dealt one of the best pass-rushers in the league, Khalil Mack, in one of the worst trades in NFL history.
The league was laughing at Gruden. The Raiders were a joke, and Gruden was the reason why.
Well, not any longer.
Gruden pulled a good, old-fashioned heist in dealing for star receiver Antonio Brown. It was such a robbery that the FBI put Gruden on its most-wanted list.
To get the best receiver in football for third- and fifth-round picks in this year's draft is astounding. This type of deal is unicorn-y. You don't see players of Brown's caliber traded essentially for a turkey sandwich, a BlackBerry and an Atari.
There's no other way to look at this other than the Steelers got absolutely smoked.
You'll find differing opinions on this trade from people inside the sport, but I think this text from an NFC West team executive speaks for a number of teams: "Everyone is stunned the Raiders were able to pull this off."
Part of how you feel about this trade depends on how you feel about Brown. To most people in the NFL, Brown is a devastating weapon. He led the NFL in receiving touchdowns last year with 15.
His dominance also isn't recent. From 2013 through 2016, Brown averaged 120 catches, 1,579 yards and 11 touchdowns a season.
The trade was a no-brainer for the Raiders, but that doesn't mean it's without risk.
Brown is a volatile figure, to be sure. He basically forced his way out of Pittsburgh by publicly trashing Ben Roethlisberger for having "an owner mentality" and questioning the Steelers' overall culture.
Some of the things said about Brown being a selfish jerk are overstated, but some of that criticism is warranted. The thorny issue for the Raiders will be what happens once Brown has footballs thrown to him from train-wreck Derek Carr instead of future Hall of Famer Ben Roethlisberger.
How will Brown react when a series of passes sail over his head or end up in the dirt?
Or, how will Brown react to the likely probability of doing more losing than winning? The Raiders have won more than eight games just once since 2011.
Those are all legitimate questions.
One thing that isn't is Brown's age. He's 30 years old, and maybe 20 years ago that would have been an issue. But not now. Brown has not only failed to slow down, but his speed and game have gotten better as he's gotten older. For many players in the NFL, because of the their diets and 21st-century workout and physical-therapy routines, 30 is the new 25.
I understand why Steelers fans are so full of salt that 16th-century ships want to set sail for them. The Steelers lost one of their own, a really good player; no matter how the Steelers, or fans, want to spin this, the fact that Brown is gone makes the Steelers a worse team. That's an undeniable fact.
Brown going to Oakland doesn't guarantee a playoff spot or Super Bowl, but it gives the Raiders something they've lacked on offense for years, and that's a true superstar.
Cooper is talented, but he's not in the same universe as Brown. If you look at the top teams in the league, each one has some sort of offensive star beyond the quarterback. The Patriots have Julian Edelman and Rob Gronkowski. The Cowboys have Zeke Elliott. The Rams have Todd Gurley. The Bears have Tarik Cohen. The Chiefs have Tyreek Hill and Travis Kelce.
A team without a great playmaker has no chance of winning a title.
Not only that, but with offenses basically allowed to do whatever the hell they want—and the rules allowing it—it's coaching malpractice not to have an Antonio Brown.
Gruden seems to be finally understanding this. Which is why it wouldn't be a shock if Gruden landed Le'Veon Bell, too. Gruden seems to be on a mission to brighten the star power of the team.
So, yes, Gruden has screwed up a lot.
Boy, did he get this one right.
Mike Freeman covers the NFL for Bleacher Report. Follow him on Twitter: @mikefreemanNFL.