How is Jon Gruden going to fix this mess he’s created in Oakland?

Jon Gruden is 1-6 in his return to Oakland, with a 42-28 blowout loss to the Colts punctuating a horrible first half of the season.

We all joked that Jon Gruden was going to lean into his comments about taking the Raiders back to 1998, but that would probably be an improvement on where things stand now. Back then, Oakland was 5-2 at this point in the season and in the middle of what would end up being a five-game winning streak.

Two decades later things are not as rosy as they were. The only link between the two seasons is the disappointment of missing the playoffs (the Raiders lost six of their last eight and finished 8-8). Oh, and Jon Gruden — he was present for disappointments past and present, and has rocked the boat in the bay so hard that the future is now something fans are actively worrying about.

After a 42-28 loss to the Indianapolis Colts, the Raiders are sitting at 1-6 through the first half of the season with little hope to cling to. Amari Cooper was traded in the middle of the week and there were reports that Derek Carr would be next. Things are dicey at best for Gruden and the Raiders, but this isn’t a one-year experiment. As hard as it is to stomach what is happening in Oakland, time will march on and decisions will have to be made that will impact the long-term future of the franchise.

What’s up with those three first-round picks?

It’s very easy to troll Gruden for all the losing he’s experiencing now, the real story of his return begins to get written in ink during the draft. Oakland owns three first-round picks, all of which right now look to land within the Top 20, and each are expected to bring in players that will be foundations for a future.

We can fully expect the Raiders pick to be in the Top 5 and be spent on a pass rusher, likely either Ed Oliver or Nick Bosa. Replacing Khalil Mack is a tall order but this is the year to be looking for help on the defensive front. The other two picks are total wild cards considering the number of needs Oakland has and depending on variables that haven’t become factors yet. If Derek Carr is gone at the end of the year, one of them will be used on a quarterback; it’s a pretty safe bet that one will be used to plug another hole on the defensive side of the ball.

No matter what Gruden does, he needs to nail at least two of the draft picks with All-Pro players that will serve as pillars of his roster. The problem with that is he’s demonstrated nothing in his past to suggest such a thing will happen. Gruden drafted 61 players while with the Buccaneers and only two ended up being Pro Bowlers (Davin Joseph and Aqib Talib). His legacy of drafting in Tampa was defined by taking Chris Simms to be his quarterback of the future, and passing on Aaron Rodgers for Cadillac Wiliams and Adrian Peterson for Gaines Adams.

Is Derek Carr part of the solution?

Aside from the massive question marks about what will happen with the bevy of draft picks, Carr’s future has been the subject of speculation this week. Throw the stupid CryingGate thing aside because it doesn’t mean anything. Carr’s future in Oakland hinges entirely on whether Gruden thinks A) he’s a guy he can win with and B) his money won’t hurt the books long term.

An underrated stat in all Raiders trading Mack and Cooper is the fact that it helped clear $74 million in cap space. Moving on from Carr would push that total to nearly $100 million and give the Raiders a lot of room to play with.

This is the small window in which Gruden might actually be a genius. Trading Mack makes sense from the standpoint that he was about to become very expensive to have on the roster. No, Ed Oliver or Nick Bosa won’t replace Mack’s productivity right away but it will give the Raiders a cheap deal on potential All-Pro talent. Similarly, moving Carr and drafting his replacement would put the quarterback on the same trajectory as the young defensive pieces and everyone’s contract fits into the same window. Gruden probably figured the team wouldn’t win in the next handful of years and instead of spending big money on contracts that would ultimately prove useless to the timeline of the roster, Gruden is approaching the Raiders roster not unlike a baseball executive. The Miami Marlins (then Florida Marlins) were roasted over the coals for winning a World Series in 1997 and instantly unloading its roster. Six years later the team won another World Series with many of the pieces it acquired in moves set up by dismantling the first championship roster.

It’s not a sustainable long-term plan as far as setting up a dynasty, but Gruden’s moves creates space to win with a very specific team on a very specific timeline. How fitting that the crazy-eyed man with a plan is taking his $100 million gamble to Vegas?

Free Agents are going to look at Gruden and think…

“Show Me The Money”, of which Gruden will show them none. If his plan is to create the foundation of a team on the cheapest dime possible, he’ll spend his money wisely on filling in the gaps. Again, this is assuming Gruden knows what he’s doing and all of this is no different than coming up with a fan theory for how Game of Thrones will end.

To his credit, Gruden has created a culture in Oakland. It’s a culture, and we don’t know if it’s a good or bad one yet but it’s very distinctly his vision. He will not stand for veterans who want to get paid and will trade someone he feels isn’t valuable to his direction. By trading Mack and Cooper, Gruden is sending a message that he is God and if you don’t want to buy into his gospel (or have what he deems is enough valuable talent) you will be turned away at the gates.

Think of Gruden as being an Al Davis cover band, a guy who knows how to play the hits but is going to do so with his own twist on things. It might not end up sounding as good as the original but if it works it’ll be hard to tell the difference.

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