From Hall of Fame talent to Hall of Fame production to NFL legend: The evolution of Charles Woodson

The football story of Charles Woodson is, at its heart, a three-part yarn. In Oakland, he had Hall of Fame talent. In Green Bay, he became a Hall of Fame player. In his return to the Raiders, Woodson became a legend. To best encapsulate these distinct chapters, ESPN Raiders reporter Paul Gutierrez and ESPN Packers reporter Rob Demovsky combined to chronicle Woodson’s road to Canton.

HENDERSON, Nev. — Charles Woodson was a young player doing young player things when he first entered the NFL, a Heisman Trophy-winning No. 4 overall pick of the 1998 draft by the Raiders.

Some days after practice, he’d hop in a car with wide receiver Andre Rison. On others, Woodson would take off with running back Charlie Garner. Jon Gruden, then a young first-time head coach himself, would look on longingly as the cars pulled out of Raiders headquarters for parts unknown and mutter to himself, “Oh, no, there he goes.”

Two decades later, Gruden laughs at the memory.

“He was broken in by some wild guys, I’ll say that,” Gruden, whose first-ever draft pick as a head coach was Woodson, chuckled recently. “We were a team full of characters. Characters with football character. And Charles was in the middle of it all.

“We were elated when he was there for us [in the draft]. It went Peyton Manning, then Ryan Leaf, then Andre Wadsworth, then us. Charles could play dime linebacker. Nickel. Corner. Safety. And all in the same series. He was one of the most decorated defensive players in the history of the draft. Yeah, we were excited. And he was a magnet, just attracting everybody to him. He enjoyed it. There were times we had to reel him in.”

Woodson rewarded Gruden and the Raiders by being named the NFL’s Defensive Rookie of the year. But if it seemed like he was distracted, or allergic to practicing, it never showed up on game day.

“Out of college, high draft pick, you’re just kind of ready for life,” Woodson reminisced. “Yeah, you’re there to play football, but you also want to live as well, you know what I mean? I was that guy. I went hard in both areas — football and then off the field, as well.”

Enter the likes of Rison and Garner. Woodson is howling now.

“Those were my boys, man,” Woodson said. “We went hard. That was the old school in me. We went hard some nights, but when it was time to get up and do that thing on Sunday, man, we were ready to roll.”

Old school?

On the football side of things, Hall of Fame cornerback Willie Brown, the godfather of the Bump and Run, gave his blessing for Woodson to wear his old No. 24.

“Willie Brown was a guy who made sure you understood what it meant to be a Raider,” Woodson said. “The first thing he would tell us, ‘There are 31 teams in the NFL, and there’s the Raiders.’ That’s the kind of mentality you picked up when you got there. George Atkinson, Cliff Branch. Those guys made me know early on what I had to bring to the table — be a tough, physical, fast football player.”

Woodson went to four Pro Bowls and was twice named first-team All-Pro in his first four seasons with the Raiders.

Woodson’s final game with Gruden as his coach? The “Tuck Rule Game.” With Woodson coming on a corner blitz, he dislodged the ball from Michigan college teammate Tom Brady in the New England snow to send the Raiders to the AFC title game in January 2002.

Except …

History books show no sack by Woodson, the fumble overturned into an incomplete pass by Brady, who would lead the Patriots to an overtime victory and hasten Gruden’s departure and the Raiders’ descent.

Sure, the Raiders went to the Super Bowl the next year (where they faced Gruden and his new team in Tampa Bay) and Woodson, playing with a broken bone in his right leg, had an interception on the third play of the game. But Gruden’s Buccaneers thumped Oakland 48-21, and the Raiders have had only one winning season and one playoff appearance since.

Injuries and issues with Gruden’s replacement, Bill Callahan, portended a frosty end to Woodson’s tenure with the Raiders. In Game 6 of the 2005 season, Woodson broke his right leg. His season was done, as was his time with the Raiders, with his contract expiring after playing the previous two years on franchise tags. And as at peace as he was with moving on, he was more excited for the coming bidding war.

“My thought was, ‘I’m going to have people crawling over each other trying to get to me,'” he said. “I thought I was that type of player.”

Except … the offers did not roll in. Not even from Gruden, who had taken Woodson to Fleming’s Prime Steakhouse in Tampa to get a feel for him.

“Probably the worst mistake of my career [not signing him],” Gruden said. “He was at a low point in his career. There were questions about fit.”

People crawling over each other to get to him? Teams were running the other way, with his recent injury history keeping him from playing in a full 16-game schedule since 2001.

“That stung a little bit,” Woodson said. “You hear players that have been through Green Bay, especially Black players, say, ‘Hey, man, that ain’t where you want to be.’

“That’s not the team I want calling me. … I couldn’t believe it. I thought there’d be multiple teams and a bidding war. It made me combative.”

‘It doesn’t happen without Green Bay’

Woodson needed the Green Bay Packers more than he cared to admit at the time.

By 2006, he had two options: the Buccaneers or Packers.

Tampa Bay wanted Woodson, but only as a safety. Woodson, then 29 years old, still believed he was a cornerback. The Packers were the only team to give him that chance.

It didn’t begin well.

It was 2006, Mike McCarthy’s first season as a head coach, and he wanted players who wanted to be there.

“Initially when I got there, things were kind of rocky at the start,” Woodson recalled recently. “I think that Coach McCarthy and everyone else around there was just trying to make my transition as easy as they could, but I was just very reluctant to allow myself to just be a Packer. We had kind of gone through some things there my first few weeks in the training camp. We had some issues that we had to iron out, but Coach Mike McCarthy assured me, ‘Hey man, we want you here. You’re going to be a big part of this team.’ He was just trying to basically comfort me as a coach and let me know I’m a big part of the plans there in Green Bay.

“Those conversations like that, we were able to have throughout my career, my seven years there in Green Bay, to the point there that Coach McCarthy and my relationship became very solid over the years I was there. I certainly appreciate him for making me feel welcome when I didn’t want to be welcome, actually.”

By Woodson’s second season, the Packers were back in the NFC Championship Game.

By his fourth season, he was the NFL’s Defensive Player of the Year.

But it was Year 5 when Woodson got what he really wanted: A Super Bowl ring.

In fact, he became a driving force behind their run to Super Bowl XLV as the NFC’s sixth seed.

In the moments after winning the NFC Championship Game over the rival Chicago Bears at Soldier Field, Woodson held court with the team huddled in the center of the locker room. He told them: “For two weeks, think about one. Let’s be one mind. Let’s be one heartbeat. One purpose. One goal. One more game. One. Let’s get it.”

The Super Bowl itself was bittersweet for Woodson; he left the game in the second quarter because of a broken collarbone. But his impact on the team was immortalized on its Super Bowl rings, which were inscribed with the No. “1” along with Woodson’s words of “mind,” “goal,” “purpose” and “heart.”

“You see that ‘1’ and the words, and it was like, ‘Wow,’ you’re floored,” Woodson told ESPN years later. “When you talk to the team in any capacity, you never know what’s going to stick. You try to say something that guys can kind of grab on to. For that to be inscribed on the ring told me that it meant something, not only to the players but to the coaches. Now, there’s something that we can actually hold on to forever.”

To say Woodson needed his time in Green Bay to solidify his Hall of Fame stats might be a stretch because, as Woodson said recently, “I would’ve been somewhere else, I would’ve made my mark somewhere else. It just so happened that during that transition from Oakland I was able to make my stop in Green Bay and go there and do some great things.”

Upon further reflection, however, Woodson conceded: “In that respect, it doesn’t happen without Green Bay, but my career was going to continue somewhere, I don’t know where it would’ve been, but I would’ve made that mark somewhere else.”

In all, Woodson spent seven years with the Packers. Aaron Rodgers has repeatedly called Woodson the best teammate he’s ever had. And when Woodson’s Hall of Fame election became official, Rodgers responded with a three-word Tweet: “The best ever.”

McCarthy, who coached Woodson during his entire tenure with the Packers, called him “a generational player,” upon his retirement.

Woodson had 38 of his 65 career interceptions in the green and gold — including a league-leading nine picks during his defensive MVP season of 2009 — and was selected to four straight Pro Bowls (2008 to 2011) while in Green Bay.

All in a place he struggled to warm up to at first.

“It was kind of rough at the beginning, because I really didn’t quite want to be there, and I just couldn’t wrap my mind around the fact that I didn’t have anybody who wanted me on their team,” Woodson said. “I was really sour about that, so it kind of dictated the way I interacted with a lot of people around there, really standoffish, got into some verbal arguments and things like that. When I look back on it I kind of feel like it was my way of trying to get out of the situation. But I’m really glad I didn’t get out of it because it turned out the way it turned out.”

‘A beautiful transition’

Looking for a new team after his contract with Green Bay expired, Woodson visited the San Francisco 49ers and Denver Broncos. Then he took a flier on the Raiders.

On May 21, 2013, Woodson visited his old stomping grounds at Raiders’ headquarters. With more than 200 fans having mobilized on social media, they, too, showed up in force to sway Woodson, some in their game-day attire of makeup, costumes and, yes, Woodson jerseys.

“I tell you, man, it was overwhelming,” Woodson said at the time. “I think that if, at any time, I had ever forgotten what the love was like in Oakland, I was definitely reminded…I think [the fan turnout] played a big part [in my return].

“I was actually afraid of leaving the facility and not having a deal done. I don’t know if I would have made it out of there. But that was a big deal and seeing that kind of welcome, it definitely put me in the mindset [where] it would be a good decision to make it happen.”

Woodson, at 37, returned to the Raiders a changed, more mature man. Beat writers who had covered C-Wood 1.0 could not believe the scene — old man Woodson, who had gone just as hard off the field as he had on, showing up for training camp toting baby car seats and strollers.

Gruden thinks the slower-paced lifestyle of Green Bay helped Woodson slow down and get centered.

“And he met and married the right woman and had kids,” Gruden said.

“It was,” Woodson said, “a beautiful transition, if you will.”

He also transitioned into a full-time free safety and did not miss a game in his three seasons back with the Raiders (he suffered a dislocated shoulder in the season opener of his 18th and final season and played through the pain), going to the Pro Bowl following his final season of 2015. It was his eighth career selection.

And yes, those were flecks of gray in his beard, epitomizing the reversed roll. Now he was playing the part of Brown, Atkinson and Branch for the younglings, which included quarterback Derek Carr, who was in the first grade when Woodson won the Heisman.

“He gets mad when I say this [but] when I was 6 years old, I was pretending to be him,” Carr said.

“C-Wood, I can’t limit his leadership to just when I played with him. He still is a leader to me. He still texts me. He still calls me. He’ll call me out and say, ‘Hey, do this.’ … He knew on his way out that Khalil [Mack] and I were coming up as the leaders of the organization … I’ll always be thankful to him.”

The Raiders struggled on the field in Woodson’s final three seasons, going 4-12 in 2013 (he recently admitted he thought he would be returning to Green Bay after that season), 3-13 in 2014 and 7-9 in 2015.

“No matter the circumstance — whether we started 0-9, which we did one year, it didn’t matter — you’ve got to go out there and work and show your teammates and coaches and fans that you care,” Woodson said. “Coming back, the second time around, everything is totally different. I’ve got two kids now. I’m married. It’s like going from driving in a 75-mph zone to driving in a 35, you know what I mean?”

Woodson, who has become an entrepreneur with his wine and bourbon labels, was such an integral part of Raiders culture team owner Mark Davis chose him to light the Al Davis Torch for the final game in Oakland.

And Sunday night, he will close out the latest chapter of his football story with the final speech of the Pro Football Hall of Fame induction ceremonies, becoming just the 10th player in history (and third Raider) to have won a Heisman and to receive a Gold Jacket.

#PFHOF21 Enshrinee @CharlesWoodson got the first look at his @HaggarCo Gold Jacket in advance of his enshrinement next week.@Raiders | @packers pic.twitter.com/jMBoi6vVlX

— Pro Football Hall of Fame (@ProFootballHOF) July 29, 2021

“It’s not one night,” Woodson said. “It’s not like I go in on the 8th and then it’s over, I’m no longer saying I’m a Hall of Famer. I’m going to say I’m a Hall of Famer on that Monday, that Tuesday, that next week, the following year.

“I’m a Hall of Famer man, so I get to celebrate that for eternity.”