Everyone has a favorite moment, a jumping-off point, an exact date, where things soured for the Raiders and sent the franchise into a spiral that continues unabated.
Some point to the Tuck Rule Game, in which the New England Patriots benefited from a little-known rule that turned a Raiders game-clinching fumble recovery into an incomplete pass in a game the Patriots won and launched their dynasty.
Others cite a career-ending injury to quarterback Rich Gannon three games into the 2003 season as the flashpoint. After all, the Raiders were 2-1 at the time, on the heels of a Super Bowl appearance, and they are 18-63 since.
Yet, everyone would agree that the common denominator in the team's alarming and precipitous decline came with managing general partner Al Davis' calculated decision to part ways with coach Jon Gruden after the 2001 season.
"Letting Gruden go was our biggest mistake," a source in the front office said. "We still haven't recovered from that decision. We should have paid him whatever it took to keep him around. Look how much it has cost us in terms of wins and losses."
Davis took a chance on Gruden when no one else dared or, at least, was ready.
Gruden was 33 at the time Davis hired him in 1998. Wise beyond his years, sure, but ready to be a head coach in the NFL? No one was quite certain.
In his third season, Gruden had the Raiders in the AFC Championship game against the Baltimore Ravens. Yet, the accomplishment was anything but a momentous occasion for the once-proud franchise.
The Raiders were on their way up, Gruden was on his way out, and perennial turmoil was just around the corner.
Davis had the option of rewarding Gruden with a new contract that paid him a salary commensurate with the league's more successful coaches or signing into effect a one-year club option for the 2001 season. Davis chose the latter. Gruden responded by making it known that his days coaching the Raiders were done once he had fulfilled his contract -- the Raiders held another one-year option for the 2002 season.
Naturally, Davis sees things in ways others can't comprehend and acts in unconventional fashion.
Instead of picking up the second one-year option and be left with nothing when the contract ran out, Davis traded Gruden to the Tampa Bay Buccaneers for two first-round and two second-round draft picks, in addition to $8 million cash, after the 2001 season -- making the infamous Tuck Rule Game the Raider finale for Gruden.
Davis promoted offensive coordinator Bill Callahan to replace Gruden and never looked back. Four games into Callahan's first season, the Raiders averaged more than 40 points, boasted a 4-0 record and asked, "Gruden who?" They then rebounded from a four-game losing streak and advanced to their first Super Bowl in 19 seasons, against Gruden's Buccaneers.
Little went the Raiders way in a 48-21 Super Bowl XXXVII loss in San Diego. Not much has gone in their favor in the five-plus seasons since, either.
Long-time senior assistant Bruce Allen bolted for the Buccaneers, taking with him the knowledge of the salary cap, the buffer zone between Davis and the players and coaches, and much-needed stability in the personnel department. The players revolted against Callahan in 2003, and he was fired two days after the Raiders finished 4-12, going from the Super Bowl to last place in the AFC West.
Callahan's replacement Norv Turner lost 23 games, control of his players and Davis' confidence in his two-year stint. Davis then attempted to right an admitted wrong by rehiring Art Shell, the man he fired after the 1994 season. Shell's old-school ways, along with his decision to bring back long-retired offensive coordinator Tom Walsh - who had been running a bed and breakfast - didn't sit well with the players. The resulting 2-14 record was the nadir in Davis' 44-year reign. Shell was fired five days after the dust settled.
So it was against that backdrop Davis set about in search of a young, dynamic coach to restore the Raiders to their glory days. The search stretched from coast to coast, from successful, proven coaches to up-and-coming ones to the inexperienced. Few, if any, had any idea what Davis intended to do with his latest move.
In the end, he settled upon USC's co-offensive coordinator Lane Kiffin, a coach who had one year's NFL experience -- he was an assistant defensive backs coach with the Jacksonville Jaguars -- and, at 31, was younger than a handful of players on Oakland's 53-man roster.
"It was a tough year," Davis said of the 2006 season at Kiffin's introductory news conference. "It was week by week and it hurt. As time went on, I realized, or at least I felt that we have to go in a different direction. We have to move the clock back. We have to get youth in the organization. We have to go ahead and attack, with someone who really means that he will attack."
Kiffin went on the attack, all right, just not in the manner Davis envisioned.
In 2007, Kiffin's offense failed to impress or shake the Raiders from their doldrums. That was how he was going to make a name for himself with the Raiders and in the NFL because he inherited a team that featured every defensive starter back from the previous season with defensive coordinator Rob Ryan and most of his assistants in place.
By the end of his first year, Kiffin launched a full-scale attack that reverberated throughout the league, lasted for nine months and precipitated another head-scratching chapter in Davis' storied career.