The Dark Era:
How the Raiders Legacy Changed When Gruden Left in 2002

As time marches forward, trampled we find the legacies of once great empires.
With time, the sheer brilliance, and greatness, of those that dominated in the past can be forgotten.
The Romans reigned for over 1,000 years. The Aztecs figured out all that they did despite being disconnected from most of the world. 
The Egyptians engineered an entire civilization in ways that, to this day, are hard to imagine.
But now, these feats are relegated to history books.
We know they were great, we read that they were. But we have long forgotten how strongly their greatness felt.
We forget how great they truly were.

Such has become the plight of the Raiders.
For decades, the team epitomized winning. A commitment to excellence. And then, suddenly, fortunes changed.
I once heard it stated that until Jon Gruden was traded from the Raiders in 2002, that the Raiders had the All-Time Highest Winning % in all of Football, and that not only that, it was in the Top 5 ever in ALL major sports (Football, Basketball, Baseball, and Hockey).
This sounded insane to me. Even if it were to be off by a little, that would be such a ridiculous feat to have accomplished over decades of sport.
And so, rather than just take it in as fact, I went out to investigate the veracity of this claim.
I wouldn’t want to repeat the statistic if it were egregiously false, after all.

And so, off I went.
Through the annals of history I scoured, pouring over the records of every single team.
684,075 Games. 7,878 Team Seasons. 123 Teams.
145 Years of Sport – going all the way back to 1876 – to get the answer.

So, just how good were the Raiders until Jon Gruden was traded back in 2002? And how did things change after he left?
He’s back now, but what damage was done in Al Davis’ now-infamous last years of team ownership?
Let’s find out.


Winning Percent (%) Until 2002

As I went back into history, immediately there was a dilemma. Out of the 123 teams that exist now across the 4 major sports, barely 38 (30.9% of all) of those teams operated in old leagues. Not only was there a lot of ambiguity raised by this, but the bigger issue was that when you go this far back in history, the competition level was nowhere near the same. There were years where there were some teams that didn’t even pay their players, going up against teams that did pay their players. What this meant was that there were, comparatively, much easier wins that franchises could amass, that modern teams didn’t have access to.

There were also, in the old era, years where teams would play teams from weak leagues that not only don’t exist anymore, but that didn’t even last long. This further presented issues with data quality. And to give another insight into just how different things were in these “really old-era” years, there were numerous seasons where there weren’t even playoffs. Teams just… kind of showed up for some games in the season, and called it a day. And in the NHL, until 1926, even if there were playoffs that season, teams from random leagues could just show up and suddenly be part of the mix, even though the skill level of these other, long-defunct leagues may not have even fully compared.

And so, there was a decision to make. Because of just how biased the oldest data could be by all of the above, really old seasons where it was much easier for teams to amass wins had to be accounted for so that, for example, there weren’t teams that’d amassed 100 extra “easy” wins that a newer team (like the Houston Texans) never had the opportunity with to pad their all-time stats. So, you don’t need to worry about the APFA Seasons that existed in football (before the NFL), the BAA Seasons that existed in Basketball (before the NBA), or any of those types of things weakening the data.

Nonetheless, whether these old seasons had been kept, or excluded to keep the data more accurate, the Raiders ranked exactly the same either way.  The Raiders and the Celtics were the only 2 teams where it actually didn’t matter if you included the “really old-era” or included them, because their ranking among all teams was exactly the same. Some other teams had notable changes to their rankings, and yet others didn’t change much at all (but had still changed). I only mention this background to the analysis for full transparency, and in case this data set proves useful for others in the future.


Raiders Winning Percentage BEFORE Jon Gruden Left in 2002 (compared to ALL Major Sports Leagues)

Out of ALL 120 Teams that existed before 2002 (in EVERY major sport), the Raiders had the 4th All-Time Highest Winning % until Jon Gruden left in 2002.
And that’s including the NBA, which is, uh… a bit broken, with just 2 teams (the Lakers & Celtics) accounting for nearly half  (45.3%) of all Championships, where at least 1 of those 2 teams has been in 54.7% of all NBA Finals ever, and where those 2 teams have somehow met in their league’s championship a ridiculous 12 times. So much for parity, I guess..

But anyway, the Raiders 4th All-Time Ranking until Gruden left in 2002 had them behind only the Dolphins, the Lakers, and the Celtics. Period.
By the way, a hard bow of respect to the Dolphins, who had the #1 all-time winning % in ALL major sports until 2002. And it was a decisive gap.

So, the claim that the Raiders were in the Top 5 of all teams in major sports until Gruden left in 2002.. turned out to be TRUE.

But now, the moment we knew was coming.
The Dark Era. The years AFTER Jon Gruden left, in 2002.
How has the team fared since then?

Winning Percent (%) Since 2002

The team had a sudden, historically bad run from 2002 to 2015. That’s 14 Seasons.
Technically there were two back-to-back 8-8 Seasons in there, but when going 0.500 was a highlight of a span that long, that’s no good.
The team averaged just 5 Wins/Season from 2002 to 2015. That was the lowest Win % in the NFL over that span (followed by the Browns, then Lions).
The 2002 Season itself is a bit of an odd one because even though it was the first year “without” Gruden, the team was still using his exact same playbook (even down to the audibles), and it was with this that the team rode its way to the Super Bowl that year to face… Jon Gruden & the Bucs. In a way, 2002 was like a year Gruden took two teams to the Super Bowl.

But now, how did the Raiders fare after 2002, when Gruden was traded? Chucky has recently returned, but what damage was done after he left?
Let us not only see, but lets contextualize it to the entire sports landscape since 2002 (so, 2002 through 2020).

Raiders Winning Percentage AFTER Jon Gruden Left in 2002 (compared to ALL Major Sports Leagues)

Wow, again. But now, for opposite reason!
Since 2002 (when Gruden left), the Raiders have just a 36.51% Winning Percentage.
Out of all 123 teams that have existed since 2002, the Raiders have ranked 121st out of 123 in Winning % over that span (2002 through 2020).

That means the Raiders dropped a whopping 117 spots compared to where we ranked in the sports landscape before Gruden left in 2002.
If we were to rank who’s experienced the biggest changes to their rank since then, we rank dead last, at 120th out of 120 Teams that existed pre-2002.

The change in rank (“ΔRank”) was done to see and highlight which franchises experienced the biggest changes to their winning nature. Teams that have remained very steady (either staying good, or staying bad) will end up in the middle. But teams that completely turned themselves around and went from losers to winners since then will get properly highlighted by very high [Green] Rank values.
— This, for example, highlights a team like the Lightning in the NHL, who have won 3 Stanley Cups since 2002 (including the most recent one);
— Or the Saints in the NFL who went from ranking 104th out of 120 teams before 2002, but have jumped a whopping +88 spots since then to have the 16th best Winning Percentage out of all 123 Teams to have existed in major sports since 2002.

Conversely, doing this highlights which teams have done the opposite. That is, which teams have had the biggest drops in winning percentage. In other words, which teams have had the biggest falls from grace?

Unfortunately, we see that since 2002, the Raiders have had the most massive fall from grace, ranking dead last over that span (120th out of 120 teams that existed pre-2002). The Raiders went from having the 4th Highest Winning % in ALL major sports before 2002, to the 121st Ranked Winning % in all major sports since 2002, meaning the team dropped a massive 117 spots to hold the unwanted title of the team to have had the biggest, negative change to where a team ranks in the entire sports landscape since 2002.

And so, we can now see just how much the legacy of the Raiders was changed when Gruden left in ’02.
Al Davis trading away Jon Gruden to the Bucs was, in a way, symbolic for the many, many other foolish moves that the historically great franchise did towards the end of Al Davis’ ownership. It also serves as a warning sign for just how much damage unmitigated and unchecked management can do. It may forever remain unclear if it was the game simply having suddenly slipped away from him, or if it was desperation toward the end of the great owner’s life, but the decisions nonetheless were inexplicably detrimental to the winning legacy of the team.

And this is unfortunate.
Unfortunate because the decisions made toward the end of Al Davis’ life are, to newer fans of football, the only ones they can associate with the team. It’s the outcomes of these decisions that have firmly implanted in people’s minds. Many fans are simply too new to watching football to realize or truly understand for just how long Al Davis & the Raiders ran a winning brand of football. Too new to understand how great the team was, and how it felt.
Before we wrap up though, I wanted to do one last thing.


Winning Percent (%) Compared to All 32 NFL Teams

(both BEFORE 2002 and AFTER 2002, when Gruden left)

Raiders All-Time Winning Percentage (compared to ALL NFL Teams)

One last thing I wanted to do was to take a step back, detach myself from the whole landscape of sports, and see just how the Raiders (and other teams) ranked against just NFL teams. After all, these should be teams we’re all familiar with. Not everyone watches every sport deeply – who’s got time for that? So, what would these rankings have looked like if we’d only compared NFL teams against each other? For that, I re-did each analysis to rank everyone accordingly. That is, I determined the ranks of every NFL team vs the NFL specifically (rather than every major sports league).

And the results were… interesting!

Out of EVERY single team in the NFL that existed before 2002, Until 2002 the Raiders had the 2nd BEST ALL-TIME Winning %.
► The only team that had a better winning %, were the Dolphins – the team that, at one point or another, had Dan Marino for 17 Seasons (who, mind you, went All-Pro his Rookie season), had the legendary coach Don Shula for 26 Seasons (still the all-time winningest coach by total wins), and oh, yeah, were the only team to this day to have a perfect season (having gone undefeated all the way through & including the Super Bowl).

On the flipside however, we also see that out of ALL 32 NFL Teams, After 2002 the Raiders had the 3rd WORST Winning % and the BIGGEST Drop in where a team ranked compared to the rest of the NFL (going from 2nd Best, to way down to 30th.. a massive 28 ranking drop!).
► By the way, holy smokes at the Patriots absolutely insane 75.0% Winning Percentage since 2002. We’ve known the Belichick era has been incredible, but seeing the rest of these numbers makes you realize just how absolutely unprecedented their run has been not just in football, but in all of the history of all major sports.

And so, we can see now that the claim about the Raiders greatness were actually true, for the most part. The team did actually have a Winning % to rank in the Top 5 of all major sports. The other claim – about the Raiders having the #1 Winning % in football specifically – turned out to be off, but only by 1 position (the Raiders we now know had the #2 Winning % in all of football until Gruden left in 2002).

BUT, the very man whose departure preceded the biggest collapse in the NFL, has come back now to the team he left, and he’s come back pissed off.

Gruden is back now. Back to rebuild the silver & black ship that for so long roamed the seas, pillaging just for fun.
And so far, the rebuild has started to come along nicely. He’s already engineered a Top 10 Offense despite a litany of issues to overcome (including an entire offseason of offensive planning wrecked as a certain wide receiver had an utterly unprecedented meltdown) and finding ways to maximize the talent he’s had. Had it not been for a historically bad defense, the Raiders would likely have been in the playoffs in 2020 (and, arguably, in 2019 as well, which just goes to show how well Gruden has maximized talent & adapted to changing conditions). Fans have been frustrated by how much fantastic work by the offense the defense has completely undone, but with a new Defensive Coordinator (and one with a history of actually using players to their strengths, unlike the previous coordinator), there is a lot of hope flowing through Raider Nation. Hope that as the Autumn Winds blow this season, we’ll once again be riding them into the playoffs. And with that, the Raiders’ return to greatness will, hopefully, be back underway! 

The Raiders long held a shining legacy. One that unfortunately spent a streak of seasons being tarnished. But as Al Davis once said, the light that has always burned brightest in the Raiders organization, is the will to win. Through it all, and with a restored commitment to excellence, with Gruden back at the helm the Raiders are back to do one thing, and one thing only. And that’s to Just Win, Baby!