The Oakland Raiders were in a tough spot during the mid-to-late 1990s. Art Shell was fired following a 9-7 finish in the 1994 season in a move that Al Davis later called a mistake. His replacement, Mike White, lasted just two years, leading the team to a 15-17 record before getting the axe himself.
Things spiraled more in 1997, as they finished 4-12 under Joe Bugel, who lasted just one season in the role. It was clear that the Raiders, whose 313-192-11 record from their inception in 1960 through 1994 was the best in football, now lacked an identity and needed a coach who could mesh with Davis.
The legendary owner was very involved in how the team played and easily earned a label of being too quick to fire head coaches. John Madden's ten-year tenure at the helm of the Silver and Black was the longest in franchise history.
As the story now has it, Davis's ownership style may have cost the franchise one of the greatest coaches of all time, setting off a chain of events that altered both the team and league history.
Jon Gruden reveals interesting connection between Bill Belichick and the Raiders
The Raiders were in a similarly bad position as they are today entering the 1998 offseason. The team was among the league's worst and in need of a complete cultural reset. Of course, Jon Gruden was ultimately named the head coach, and they picked Charles Woodson with the No. 4 pick that year.
Both of those moves, of course, were overwhelming successes for the Raiders, and they had similar career paths with the Silver and Black. Gruden recently appeared on Julian Edelman's Games with Names podcast, where he revealed that Bill Belichick was actually the franchise's initial target.
"Bill Belichick had the job. He was going to get the head coaching job. He called me, says, 'Hey, do you want this job?' Like, what are you talking about? 'Do you want the Raiders job?' I go, 'Yeah, I do.' He goes, 'You can have it, I'm pulling my name out.' There were a lot of people that said, 'You want to ruin your career? You go work for [Al Davis].' Because people have been fired and fired and fired and fired."
Now, some have argued that Davis always wanted Gruden and that while Amy Trask wanted Belichick, Davis always won out, and he would have with Gruden. But it's hard not to imagine how much of the NFL's history would be rewritten if the Raiders had hired Belichick.
Belichick, who was the New York Jets' assistant head coach and defensive coordinator at the time, remained in that role before returning to a head coaching role in 2000. Of course, that was originally supposed to be with the Jets; however, he resigned after one day to join the New England Patriots.
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His decision to spurn the Raiders, ultimately, hurt the franchise in more ways than one. Losing Belichick as a coach was a tough enough blow. The bigger blow, however, came in the 2001 AFC playoffs, as his Patriots beat Oakland 16-13 in what is now known as "The Tuck Rule Game."
The loss was one of the most crushing defeats in Raiders history, as the game should have been over on a Tom Brady fumble that was inadvertently overturned to an incomplete pass. Making matters worse, New England went on to win the Super Bowl, kickstarting a dynasty that resulted in six titles.
Meanwhile, it also turned out to be Gruden's final game coaching the Raiders until he was re-hired in 2018. The young, up-and-coming head coach was traded to the Tampa Bay Buccaneers for two first-round picks, two second-round picks, and $8 million in cash.
While that may sound like a haul, it was another move that hurt the Raiders. The next season, Gruden's first in Tampa Bay, Oakland finally got over the hump and won the AFC, reaching the Super Bowl for the first time in nearly two decades, only to be met by their former coach, who knew the playbook.
The result? A blowout 48-21 loss for the Raiders. The franchise has yet to recover from that loss, either, as they have not won a single postseason game since that 2002 season, reaching the playoffs just twice.
While the hope is that Klint Kubiak and Fernando Mendoza can finally right the ship, one can't help but wonder what the league would have looked like if Belichick accepted Davis's reported coaching offer.