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Jon Gruden leads Raiders vs. 49ers on Yahoo Sports app, but can he lead a rebuilding job?

Frank Schwab
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The easiest thing in the NFL right now, other than praising Patrick Mahomes, is cracking jokes about Jon Gruden.

Every wisecrack has been earned. The Khalil Mack trade alone will be incredibly tough for Gruden to live down. The Oakland Raiders are perhaps the NFL’s worst team at 1-6, and finish the first half of their season against the San Francisco 49ers on Thursday night, a game that can be livestreamed on the Yahoo Sports mobile app (IOS and Android).

The 49ers are 1-7 and in bad shape this season too, but that turns around right away when quarterback Jimmy Garoppolo returns next year from ACL surgery. There’s no similar hope for the Raiders, who started the season with the oldest roster in football (h/t to Philly Voice) and have been abysmal.

Or is there hope? Before we crack more easy jokes about Gruden, let’s at least allow the possibility that there’s some kind of method to all of his madness.

Raiders have stocked up on quality draft picks

You’re going to hear this a lot after this season is over, but the Raiders have stockpiled five first-round picks over the next two years including three next year. Given that their own picks, especially in 2019, might be very high in the draft, that could help build a nice foundation.

We’ll get to Gruden’s draft history in a moment — spoiler alert, it’s not pretty — but this year’s draft class doesn’t look that bad. Left tackle Kolton Miller, the first-round pick, hasn’t played great but he was put in a tough position and is learning on the job. Defensive linemen Arden Key and Maurice Hurst, third- and fifth-round picks, respectively, have shown promise. Offensive tackle Brandon Parker, a third-round pick, is starting. Punter Johnny Townsend is contributing. Cornerback Nick Nelson has made it back from a pre-draft injury and could be a good player down the road. There’s not historic potential in this Raiders draft class, but it’s a start.

After the last few drafts have been mostly washed out with almost nothing left on the roster, the Raiders needed at least a couple young players to hit, and it appears that is happening. And there’s a surplus of picks coming the next couple years. The Mack trade was bad, but getting a first-round pick for chronically unproductive Amari Cooper seems to be a win. Not all of Gruden’s moves have been awful.

Jon Gruden’s draft history isn’t good

The problem might be that Gruden will be the one making those extra picks. Josh Dubow of the Associated Press pointed out that it’s not like Gruden was hitting draft pick home runs during his time with the Buccaneers.

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That’s scary. But, it was a long time ago he was flubbing those drafts. Maybe he has learned.

Also, the Raiders are in good shape cap-wise. That’s a little bit of a poisoned chalice, because the reason the Raiders have a ton of cap space is that they barely have any good players to pay. Still, they’re fifth in projected cap space next year by Spotrac and aside from Derek Carr and the good young guard tandem of Kelechi Osemele and Gabe Jackson, there’s no significant long-term commitment to anyone beyond 2019.

The Carr question is concerning, because he plays the most important position in the NFL. He’s seemingly regressing, though he’s only 27 years old, in his first year in a new system and his 2016 was very good. If he can make progress in the second half of the season and convince Gruden he’s the quarterback of the future, that allows for the Raiders to use all draft capital and cap room to build a good cast around Carr.

In 2016, the Raiders looked like one of the best young teams in the NFL. That is long gone in just two years, but it shows that fortunes change fast in the NFL. It’s fair to have every question about whether Gruden is capable of pulling off a resurrection, but he has more than enough resources for it.

Gruden has time to turn it around

Gruden isn’t exactly a rube, or unsophisticated in the ways of the NFL. He has been around the game for decades. It’s possible he saw the decay of the Raiders roster, especially after so many bad drafts, and understood it needed to bottom out before it got better. Someone with a 10-year, $100 million contract can execute a long-term plan.

Other than trading Mack, which was just a bad mistake, which other player that Gruden dumped has gone on to big things? Michael Crabtree and his 440 yards and two touchdowns in Baltimore? Marquette King, who wore out his welcome almost instantly in Denver? Exactly. The roster was going to be bad pretty much no matter what Gruden did.

That’s not to say Gruden is a secret evil genius. Maybe he’s just a guy who was overrated in Tampa Bay (he was 45-51 his last six seasons there with no playoff wins) and leveraged his reputation and television celebrity into a big contract, even though the game has severely passed him by. That’s what most people would say, and they might be right.

But Gruden will have a chance to prove everyone wrong the next few years, with his war chest of picks and cap space. There’s still time for Gruden to get the last laugh.

Oakland Raiders coach Jon Gruden has at least stockpiled picks and cap space to rebuild his team the next few years. (AP)
Oakland Raiders coach Jon Gruden has at least stockpiled picks and cap space to rebuild his team the next few years. (AP)

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Frank Schwab is a writer for Yahoo Sports. Have a tip? Email him at shutdown.corner@yahoo.com or follow him on Twitter!

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