And it's easy to believe such a trade will happen. Not only because Bleacher Report's Master Tesfatsion reported on Saturday that the Raiders were "shopping" Carr at the NFL Scouting Combine in Indianapolis, but also because Gruden has been selling off parts since arriving in the Bay Area 14 months ago.
But it's one thing to part ways with an expensive, high-caliber pass-rusher entering a contract year or a blue-chip first-round wide receiver in the final guaranteed-money season of his rookie deal.
It's another thing to deal away a 27-year-old passer in his prime, especially when said passer is just a couple years removed from a Pro Bowl season in which he earned a half-dozen MVP votes.
I know, Carr has not been as effective the last two seasons as he was during that breakout 2016 campaign, and he's due to make $86 million over the course of the next four years from an organization that probably isn't on the brink of a Super Bowl run.
The Raiders are clearly rebuilding following a series of decisions from Gruden that sent key veterans Khalil Mack, Amari Cooper, Michael Crabtree and Bruce Irvin packing in 2018, but rebuilds done right in this era of NFL football are often short and relatively painless.
The Raiders can become the league's latest quick-turnaround rebuilder. All they have to do is avoid overdoing the tear-down portion of the process. Trading a three-time Pro Bowl quarterback with just five seasons under his belt would be over the top, and there's a high probability it would backfire. Here's why.
1. The draft has always been a crapshoot at the quarterback position
Maybe the Raiders are enamored by Kyler Murray, as odd as that would be for Gruden—a coach known for his appreciation of quarterbacks with prototypical measurables. Maybe they think Dwayne Haskins has a higher ceiling than Carr. It's possible they'd be willing to trade Carr to a quarterback-needy competitor and then use their initial first-round pick on Murray or Haskins.
But this is not a strong quarterback draft class to begin with, and there are legitimate reasons to be concerned about both of those prospects.
And even in good years, there are no guarantees at that position. The Raiders could wind up with a Matt Ryan or a Cam Newton, but they could just as easily end up with a Joey Harrington or a David Carr, a JaMarcus Russell or a Matt Leinart, a Jake Locker or a Vince Young, a Mark Sanchez or a Robert Griffin III, a Byron Leftwich or a Blake Bortles.
Among the 45 quarterbacks drafted in the first round between 2000 and 2016, only nine have made as many Pro Bowls as the 27-year-old Carr.
2. Free-agent quarterbacks are usually free agents for a reason
Don't you dare try to claim Nick Foles would be an upgrade over Carr and that Oakland would be better off trading Carr for a high draft pick and signing Foles. That wouldn't likely save the team a dollar and would probably handcuff it to an older, less broadly accomplished and frankly less skilled quarterback for a longer period of time.
If indeed the Raiders feel they'll be locked in a rebuild for several more years, cutting costs and gambling on a rookie makes at least some sense. Jumping from Carr to another highly paid veteran does not, and rolling the dice that Foles—who hasn't experienced sustained success in a half-decade—would bring his Super Bowl magic from the Philadelphia Eagles would be a tremendous mistake.
Another factor is it's entirely possible they'd miss out on Foles in free agency or Murray or Haskins in the draft, which makes a Carr trade that much more risky.
3. The Raiders could be trying to fix what ain't broke
It's not as though Carr is a one-hit wonder feeding off a fantastic 2016 season. He was also a Pro Bowler with 32 touchdown passes as a sophomore in 2015 and was again voted in despite struggling at times in 2017.
In his defense, there's a strong probability that Carr's numbers declined that year at least partly due to the fact that he was coming back from a broken fibula, and he later suffered a transverse process fracture in his back that likely affected him for the remainder of the year.
And while a healthier Carr failed to lead the Raiders to even a handful of victories in 2018, he had less support than ever as a result of Gruden's fire sale. I mean, the man was running a new offense with dudes like Doug Martin and Seth Roberts playing key roles, and his defense surrendered a league-high 29.2 points per game.
Despite that, Carr quietly posted the highest completion percentage (68.9) and yards-per-attempt average (7.3) of his career. His passer rating was 97.2 from mid-October on, and he threw just two interceptions in the final 11 games of the regular season.
How much better could he be with an improved supporting cast? Carr already proved in 2016 that he's an incredible clutch performer, but he hasn't had many opportunities to work in pivotal moments since then.
Carr got those six MVP votes despite breaking his leg in Week 16 that season, and he probably would have earned quite a lot more if not for that freak injury.
You can't give up on a player like that in such a short span.
Give it a year
The only reason to trade Carr now is if you've fallen in love with Murray, Haskins or Foles. But we've learned that falling in love is a foolish thing to do in this league. If they're tempted by a potential Carr trade, the Raiders have to shake themselves and keep in mind that the 2020 quarterback draft class is supposed to be stacked.
What's the rush to trade Carr right now? They'd save $15 million against the salary cap, but is that really a concern for a franchise that, according to Spotrac, is slated to enter the new league year with nearly $70 million in cap space?
Maybe you can get a first-round pick for the guy, but that could also be the case in a year or two. And the Raiders have five first-rounders in the next two drafts, so they have no reason to crave more of 'em.
Carr could lose value with a poor 2019 season, but it'd be a lot cheaper to cut or trade him next offseason, and the supply-and-demand dynamics at that position probably mean he'll be worth some draft capital regardless of what transpires in 2019.
From both a financial and a logical standpoint, it makes sense for the Raiders to wait this out. Quarterbacks are so well-protected now that their shelf lives are longer than players at any other skill position, so there's little reason to panic on Carr.
Wanna bet the Indianapolis Colts are happy they didn't do so with quarterback Andrew Luck? He wasn't quite right for several injury-plagued seasons before missing all of the 2017 campaign, but Indy didn't give up on him, and a 29-year-old Luck got back to the Pro Bowl with the highest-rated season of his career in 2018.
Let that be a lesson.
Another premium draft pick might be enticing, and another monumental change might be intriguing. With a move to Las Vegas on the horizon, a big splash at the most critical position on the roster is understandably tempting. But the Raiders have to realize that they're better off keeping Derek Carr for at least one more year.
Brad Gagnon has covered the NFL for Bleacher Report since 2012.