The team hasn't had a winning season since 2002, and recently deceased former owner Al Davis never had a tolerance for losers. Since Art Shell left the franchise in 1994, the Raiders have only had one head with a winning record: Jon Gruden, who compiled a 36-28 record in Oakland and led the team to one AFC championship and nearly another (the Snow Bowl and the tuck rule be darned) during his four-season tenure.
Gruden, like many other Raider coaches who came before him, had a falling out with Davis and, in an unusual move, was traded to the Buccaneers for cash and draft picks. The next season, the Raiders, under Bill Callahan, made it all the way to the Super Bowl, where they were thoroughly trounced by the Buccaneers, led by Gruden, of course.
Callahan was let go the next season, and, over the ensuing 10 years, Davis went through a who's who of NFL and college coaches only to unceremoniously dismiss them all.
Despite the loss of Davis Sr. (the team is now run by his son Mark), the Raiders appear to be reigniting their coaching carousel. This season, they're 3-9, and ever-so-soft rumblings about head coach Dennis Allen's job security can be heard.
On Monday, Yahoo Sports reported that the team has reached out to Gruden about a return to Oakland. Gruden hasn't coached in the league since 2008, when he was let go by the Bucs. Since then, he has provided color commentary for Monday Night Football.
Take the Gruden/Raiders rumors with a grain of salt, though. Last week, it was also reported that he was in talks to become the University of Tennessee's new head coach.
Publicly, Gruden has said he remains committed to ESPN, but sources close to the former coach say he's entertaining offers to return to the sidelines.