You won’t see another resume as impressive as Charles Woodson’s. That’s not opinion, it’s a fact. No other man on earth has checked all these boxes:
Heisman Trophy
That means he’s won at every level, both on a team level as well as every personal award possible.
But even with all that, there was one thing that eluded Woodson in his career.
“Winning a Super Bowl with the Raiders,” Woodson said without hesitation. “I feel like that’s the one thing that got away from me, man. To be able to win a Super Bowl in the Silver & Black, man, if I could’ve accomplished that, on top of all the other things – and don’t get me wrong I’m not complaining – but, man, to have won it with the team that drafted me…Getting there was great, but, man, if we could’ve closed that deal, I would’ve definitely said ‘You know what, I did it all.”
Woodson got close to helping the Raiders to a Super Bowl win a few times. First in 2000 when the Raiders made it to the AFC Championship game, but lost to the Ravens.
Then the following year when Woodson forced the would-be game-ending fumble on Tom Brady only to have it overturned by the improper implementation of the now defunct Tuck Rule.
Then finally in 2002 when the Raiders made it to the Super Bowl only to face their old coach Jon Gruden.
The Raiders fell off after that and a few years later, Woodson would be allowed to leave in free agency to sign with the Packers. That’s where he would eventually get his ring in 2010.
Getting his ring came a year after Woodson won Defensive Player of the Year. And a year later, at the age of 36, Woodson was asked to switch to safety, which for many defensive backs, signaled the end of his career.
But not for Woodson. He had unfinished business.
Woodson returned to the Raiders at the age of 37 and played three more seasons before finally stepping away from the game.
Right to the end, even with nothing left to prove, Woodson was not going to go out with a whimper.
“Making it through that season was a feat in its own self,” Woodson said of his final NFL season. “In that first game I dislocated my shoulder, and then the third game of the season, playing against the Browns, I suffered a grade two MCL sprain and, man, every day from that game forward… And then even against the Bears, I suffered a left shoulder sprain, and, aw man, it was hard each and every game to get myself in position to practice, just the little bit that I could practice to go into the game and still have to play at a high level and to go through all that and to actually in my 18th year, make a Pro Bowl, having gone through all that, I feel like that was a career all wrapped up into that 16-game schedule.”
“I just kept telling myself… I’m not going to spend my last season on the sideline.”
Though all that, Woodson would make his ninth Pro Bowl at the age 39 and at a second position before riding off into the sunset.
He obviously never got to hoist the Lombardi Trophy in Silver & Black. But he gave everything he had to the team that drafted him. From the moment he set foot on an NFL to the day he left it for the last time.
He may have took a trip to Green Bay for a time to get his ring, but he has never really left the Raiders.
