According to Schefter and Mortensen, the Raiders would be prepared to offer Gruden an ownership stake in the team to lure him out of his analyst role on Monday Night Football for ESPN. The Raiders would also empower Gruden to "reshape the front office, coaching staff and entire organization."
Pro Football Talk's Mike Florio reported it's a "coin flip" as to whether the Raiders will fire head coach Jack Del Rio at the end of the 2017 season.
Schefter and Mortensen noted Del Rio and Gruden share an agent, which creates a headache for Oakland if it's serious about targeting Gruden.
The Athletic's Tim Kawakami tweeted the Raiders might be tempted to make a major coaching splash, which is why they're going after Gruden:
The sentimental pull of hiring Gruden is obvious. The 54-year-old coached for four years in Oakland—compiling a 38-26 record—and he helped lead the Raiders to the AFC Championship Game in 2000. A large number of Raiders fans would likely welcome him back with open arms.
Gruden has also become something of a quarterback guru through his QB Camp series on ESPN ahead of the NFL draft every year. In that sense, he'd be a good fit with Derek Carr, who has regressed in 2017. After throwing for 3,937 yards, 28 touchdowns and six interceptions last year, Carr has 3,253 yards, 21 touchdowns and 12 interceptions through 14 games this season.
However, there would be a few potential pitfalls to hiring Gruden.
For one, he hasn't coached since 2008. The NFL has changed significantly since then, and while Gruden has remained close to the game, working as an analyst isn't the same as working as a head coach.
Gruden didn't exactly have a ton of success beyond his Super Bowl win with the Tampa Bay Buccaneers in 2002, either. Between 2003 and 2008, the Buccaneers made two playoff appearances and exited in the Wild Card Round on both occasions.
The Raiders would be adding even more risk by giving Gruden so much internal power. The Philadelphia Eagles made a similar move with Chip Kelly in January 2015, and it was such a disaster they fired Kelly before the year was over.
Rehiring Gruden nearly 16 years after trading him to the Buccaneers would energize a fanbase that has grown upset over the franchise's impending move to Las Vegas and lack of success (one playoff appearance since Gruden's exit), but it would be a massive risk all the same.