How Jon Gruden has been a hilarious, expensive disaster for the Raiders

The Raiders brought back Gruden for a mere 10 years, $100 million, and things are not going well.

NFL teams have been trying for years to lure Jon Gruden out of the Monday Night Football booth and back to the sidelines. The Oakland Raiders finally pulled it off, and all it took was an unprecedented 10-year, $100 million contract.

Be careful what you wish for.

Gruden’s tenure so far has been a bumpy ride for Raiders fans. But one thing that’s become clear, is that he’s tearing down the existing team and rebuilding the one he wants. With FIVE first-round draft picks over the next two years, Gruden figures to have his young nucleus in place by the time the team permanently sets up shop in Las Vegas in 2020.

Offseason moves

His tenure started with hahaha lots of jokes about bringing back a very 1990s brand of football. He backed that up in free agency. Productive players like receiver Michael Crabtree and cornerback Travis Carries were sent packing. Aging players like Jordy Nelson and Derrick Johnson were brought in to beef up the roster.

The Khalil Mack trade

Gruden’s coup de grâce of roster rebuilding came right before the season started, when he traded all-world pass rusher Khalil Mack to the Chicago Bears for a pair of a first-round picks. That left Bruce Irvin as the lone pass rushing threat, and even Gruden himself has remarked just how badly the Raiders need to sack quarterbacks AND how hard it is to find good pass rushers.

Of all the moves, this one might be the hardest to swallow. Versatile pass rushers in the prime of their careers don’t come around very often. Even with the kind of contract extension Mack was looking for, it probably would have ended up being a bargain in a year’s time.

More trades

Just over a week from the NFL’s Oct. 30 trade deadline, the Raiders made another move. This time they sent fourth-year wide receiver Amari Cooper to the Dallas Cowboys for ANOTHER first round pick.

Cooper’s had his struggles in the last two year’s with the Raiders. Sometimes it felt like he dropped more passes than he caught. And while it’s a short-term hit for the Raiders skill positions, getting a first-round pick for Cooper was better than most experts expected.

And he might not be done.

It’s Gruden’s team

It’s clear Gruden has cemented a commanding role on personnel matters, setting up a potential fracture with incumbent general manager Reggie McKenzie over previous years. Worse, Gruden’s got a personnel Svengali who’s famous for making bad takes on Twitter.

None of it matters, not the bad roster moves, questionable coaching decisions, or any of it ... not yet, anyway. The Raiders are building a team for 2020, one that, ideally, can hit the ground running when they get to Las Vegas soon. And Gruden is Gruden, a brand name like that with a contract the size of a small state’s GDP gets a grace period.