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 pulled it off, and all it took was an unprecedented 10-year, $100 million contract. Now, following a humiliating 34-3 loss to the 49ers and their third-string QB in Week 9, Gruden’s Raiders are 1-7, spiraling into oblivion.
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. To the surprise of nobody, the team fired general manager Reggie McKenzie on December 10. Helping Gruden fill in on personnel matters is 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.
Jon Gruden should give the Raiders their money back like he promised

Photo by Thearon W. Henderson/Getty ImagesI suppose Mark Davis, the good for nothing son that’s a staple of privileged families everywhere, believed he was pulling off a real coup when he was the one to finally lure Jon Gruden out of the broadcast booth and back on the sidelines. There must have been some oedipal shit going on there too — rehiring the brand name coach that Al Davis, his father, got rid of and doing it with a 10-year, $100 million set of shackles.
Making costly, franchise-altering decisions is baked into the Raiders’ DNA.
Read Article >NFL head coaches said some really dumb s**t this week

Photo by Jonathan Bachman/Getty ImagesIf you look at the totality of the NFL coaching ranks, it’s getting better. The league’s started to weed out dinosaurs who depress the product. However, this is not an institution that enthusiastically embraces change. Two steps forward, one step back. And this week has has been a banner week for head coach hubris, including two of the NFL’s most ossified skippers.
First up is the $100 million man himself. Gruden’s dumb quotes are endless and well-documented, so this one is fairly innocuous by those standards. But it’s still pretty dumb!
Read Article >Ranking Jon Gruden’s best quotes in his Raiders return, from Khalil Mack to Tom Cruise

Photo by Matthew Stockman/Getty ImagesWhen the Oakland Raiders hired Jon Gruden in January, they weren’t just getting a coach — they were getting a character and the show that comes with it.
After nine years as an ESPN personality, Gruden’s return to coaching has brought with it hilarious quotes on a weekly basis. And that’d be a lot more fun for Oakland if it was paired with some wins, but so far the Gruden era has mostly been losses and a skunked up locker room.
Read Article >The Raiders have 99 problems but Derek Carr crying isn’t one

Photo by Warren Little/Getty ImagesThe Oakland Raiders are 1-5 and, in the last two months, they’ve traded the only two Pro Bowlers they’ve drafted in the first round since 2004.
With three first-round picks in the 2019 NFL Draft and two in 2020, it’s clear Jon Gruden is playing the long game for the Raiders with a relocation to Las Vegas on the horizon. But that doesn’t give players on the roster much reasons for optimism.
Read Article >Raiders trade Amari Cooper to Cowboys for a 1st-round pick. Congratulations, Jon Gruden

Kyle Terada-USA TODAY SportsThe Raiders’ fire sale is back on. On Monday, Oakland’s roster makeover continued when the team shipped former No. 4 overall pick and two-time Pro Bowl wide receiver Amari Cooper to the Dallas Cowboys in exchange for a 2019 first-round draft pick.
It’s another major move for head coach Jon Gruden, who has taken a machete to the Raiders’ roster since arriving as the team’s $100 million coach this offseason. After releasing players like Michael Crabtree and Marquette King, he engineered possibly his boldest move by trading 2016 defensive player of the year Khalil Mack (and a second-round pick) to the Bears for two first-rounders and additional draft considerations.
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