Charles Woodson Faces Tom Brady Again, Now as Browns Owner

Yahoo

11-06-2025

The Super Bowl isn't just a game—it's a giant convention, a who's who of football money, where the members of the sport's ownership class rub shoulders and make deals. During the run-up to last year's event in Las Vegas, Cipriani, the upscale Italian eatery at the Wynn Plaza, served as the backdrop for one such meeting, featuring one of the game's most accomplished players and an NFL power couple. Hall of Famer Charles Woodson dined with Cleveland Browns owners Jimmy and Dee Haslam, along with their daughter-heir Whitney and her husband JW Johnson.
For nearly two hours, the Haslams and the Fox broadcaster discussed an array of topics, from football and team operations to Woodson's humble upbringing in Fremont, Ohio. Woodson, named Ohio's Mr. Football in 1994 after a stellar career at Ross High School, told the Haslams that even in his wildest dreams, he could never imagine being an owner of his hometown NFL team—the same storied franchise that drove him to become a pro football player.
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Woodson left Las Vegas optimistic about the conversation. However, he still had no real indication that the Haslams would offer to sell him a stake in the Browns and let him become the franchise's first outside minority partner in their family ownership group.
'It could've gone either way from there,' Woodson said in a phone interview. 'It was a great meeting, at least I felt like it, but you never know how someone is feeling on the other side. From there, I didn't know anything.'
The interest was, in fact, mutual. Woodson and the Haslams sat down again for another meeting near Woodson's home in Orlando, Fla., during NFL owners' meetings a month later. The family eventually invited him out to Browns headquarters in Berea to tour the team's facilities and training grounds and meet with team executives and staffers. Woodson soon received a formal offer to join the ownership group, a minority deal approved by NFL owners last month. He reportedly paid $5 million for his .01% stake.
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'I'm from a working-class community, so ownership was never part of my [previous football] conversations,' Woodson, a nine-time NFL Pro Bowler who retired in 2015, said. 'But I feel like I deserve the opportunity for what I was able to give to the game. In some ways, I feel like this is the game repaying me back, and I'm thankful for that.'
Woodson isn't the only Fox employee to be an NFL limited partner; Tom Brady, Woodson's friend and former Michigan teammate, officially bought into the Raiders last year. Woodson and Brady are tied together in NFL history through the infamous 'Tuck Rule' game in 2001, but the two remain close more than 20 years later. He says the former New England Patriots quarterback reached out to him to send a note of congratulations last month. The two will fight for bragging rights when the Raiders host the Browns on Nov. 23.
'Here's two guys who came into the University of Michigan together in 1995, and here we are [30] years later and now we're both NFL owners,' said Woodson, who won a national championship and Heisman Trophy with the Wolverines. 'How about that? We're co-workers and opponents again.'
Woodson, 48, is the latest former pro athlete to join an NFL ownership group. His purchase highlights the league's push to diversify ownership. The last few years have featured a swath of diverse leaders joining the league as limited partners, from former Olympic gymnast Dominique Dawes (Atlanta Falcons) to a trio of former Toronto sports stars in Vince Carter, Tracy McGrady and Jozy Altidore (Buffalo Bills).
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Both of those deals were orchestrated by Shepherd Park Sports CEO Derrick Heggans. The former NFL attorney with close ties to league owners also played an integral role in Woodson connecting with the Haslam family.
The former All-Pro defensive back's entree into the Browns ownership started with a phone call a couple years ago from former Arizona Cardinals star Larry Fitzgerald, who plays golf alongside Woodson every year at the American Century Championship celebrity tournament in Lake Tahoe, Nev. Fitzgerald, a savvy investor who once owned a stake in the NBA's Phoenix Suns, asked Woodson if he'd ever considered team ownership. If so, he said he should meet with Heggans. Soon after, Heggans and Woodson were discussing possible cap table openings, including with the Las Vegas Raiders, the franchise for which he played 11 of his 18 NFL seasons.
Heggans ultimately convinced Jimmy and Dee Haslam to consider Woodson, given his football championship pedigree and deep roots in the Buckeye state. 'He's a favorite son of Ohio,' Heggans remembers telling Jimmy Haslam. 'Once you're that, you're always that. … Ohio is proud of Charles Woodson and would love to welcome him back home. He becomes your secret weapon.'
As a part team owner, Woodson, like Brady, will be subjected to the league's broadcast restrictions—he will be barred from production meetings with owners and players, and he will not be able to enter other teams' facilities. He says it's not a problem due to his studio analyst pregame role on FOX NFL Kickoff.
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'[Brady's] job is much different than mine,' Woodson said. '[Brady] has to have much more of a touchpoint with each team that's playing each week where he's the analyst. He's more intimate with that process, so he's got a lot of restrictions on him and what knowledge he's privy to.'
Woodson says his job 'is a different animal.'
Being a limited partner in an NFL team may also impact Woodson's other ventures. He owns a liquor company (Woodson Whiskey) and wine company (Intercept Wines), and reports have stated he will have drop the 'Woodson' name from his whiskey venture, since the NFL's alcohol policy states no team owner can use their name, image and likeness for promotional purposes.
Woodson says he hopes his new ownership position will be beneficial for his brands from an awareness standpoint even if that means potentially changing the way he promotes his businesses. The Super Bowl champion has ambitions of marrying his former and current ventures, hoping to make his wine company a leaguewide NFL partner, like California-based Barefoot Wine.
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Woodson, nonetheless, is pumped to be part of the Browns' organization. He looks to contribute in a variety of ways, including with on-field matters, he says, if head coach Kevin Stefanski and the front office are interested in his perspective.
When he's not handling his Fox analyst duties or elevating his businesses, he's spending time as a defensive coach for his son's high school football team (Lake Nona) in Orlando, Fla. But now he can also add owner to his lengthy football resume. It's a dream come true for the kid from Fremont.
'It's incredible news,' he said. 'Incredible.'
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