Charlotte Jones is the mastermind who made the Dallas Cowboys the most valuable team in the world—yes, the entire world—with a Forbes valuation of almost $9 billion. She did more than simply put logos on billboards as the team’s chief brand officer and created a sponsorship machine that attracted massive relationships like Bank of America, Ford, AT&T, and PepsiCo. Led the design and marketing strategy behind The Star in Frisco, the team’s futuristic $1.5 billion HQ and practice facility that doubles as a commercial hotspot. And created a lifestyle empire out of a football brand.

She just stepped into the ring, and Serena Williams is her opponent—not a rival NFL executive. It’s NFL royalty vs tennis royalty for a slice of the league’s next golden goose. Flag football isn’t just the NFL’s growth hack—it’s a branding war.

As reported by Front Office Sports, Charlotte Jones is involved in a Dallas-based investment group aiming to buy into the NFL’s planned professional flag football leagues. The NFL has stayed tight-lipped about specific bidders, but the interest is heating up fast.

And this is not a random move. The NFL’s pro flag football initiative is calculated as Charlotte Jones’ is not just dipping a toe in. She’s going full throttle into the NFL’s next billion-dollar battlefield. With 20 million players in more than 100 countries and the sport expected to make its Olympic debut in 2028, flag football is the NFL’s ticket to international growth and new audiences.

“We do believe as it grows in popularity, that there is room for more leagues, including a professional league, and that would clearly have a media package as well,” said Brian Rolapp, the NFL’s chief media and business officer. “We’re very early in this. The commissioner talked about it. … So I think we’re pretty bullish on it.”

Once the flag football leagues are up and running. The NFL intends to sell media rights, and the value of such rights packages could skyrocket. We’re talking ESPN, Amazon Prime, YouTube TV and Netflix. When you add up media rights, sponsorships, franchise sales, and international licensing, the long-term value of these endeavours may well approach $111 billion, according to media experts.

Enter Charlotte Jones. She’s familiar with branding and football. She’s been the Cowboys’ voice in the NFL’s most powerful boardrooms, serving as chair of the NFL Foundation, where she’s overseen the league’s community outreach, player health initiatives, and charitable partnerships. From halftime performances to sophisticated fan interaction tactics, Charlotte also contributed to the transformation of the Cowboys’ game-day experience into a full-fledged entertainment extravaganza. When Jerry Jones flexes his power in NFL circles, make no mistake—Charlotte’s fingerprints are all over the playbook.

But there are other high-profile bidders in the ring. Serena Williams has indicated an interest in owning one of the first flag franchises, and Alexis Ohanian’s Seven Seven Six venture group has already put in an application. Serena is not just tennis royalty,  she’s a business entrepreneur with investments in more than 60 businesses through Serena Ventures. And the face of international advertising campaigns for brands like Nike, Gatorade, JPMorgan Chase, and others. She has appeared on the cover of Vogue. Co-chaired the Met Gala. And started a $111 million venture fund that supports minority and women-led companies.

So now, we’ve got two Titans—one from inside the NFL bloodline, and one from outside it—chasing the league’s next gold rush. And while Charlotte Jones carving out a future for the sport, her father—Jerry Jones—is catching heat for clinging to the past.

Inside Jerry Jones’ $240M gamble

Jerry Jones is a proud father. But he also gave Dak Prescott a $240 million contract that is already deteriorating. The contract, which Dak signed shortly before the start of the previous season, pays him an average of $60 million a year, making him the highest-paid player in NFL history. Not Mahomes. Not Allen. Prescott. A quarterback who is 31 years old, has two playoff victories in nine seasons and has a lengthy injury history.

Now, that investment is under the microscope. Bleacher Report just ranked Prescott the second-most overpaid player in NFL history. “He has missed large chunks of three of five seasons in his prime,” the report says, “and he’s continually come up short when it matters.” In 2023, Prescott had his best statistical year, finishing second in MVP voting. But in true Cowboys fashion, it ended in a humiliating playoff upset. Again.

Now, Cowboys fans are furious. The contract hasn’t just hurt the team’s flexibility. It’s become symbolic of Jerry Jones’ blind loyalty to a player who hasn’t delivered. With a quarterback who has been eliminated in the Divisional Round. Every playoff loss adds fuel to the fire. Every passing year without a deep run makes the $240M look less like an investment and more like a vanity deal.

Here’s the irony: While Jerry Jones is being flamed for betting on the wrong star, Charlotte is quietly positioning herself to ride the next wave of football innovation. As the Cowboys limp into another “prove-it” year, the most powerful person in the organization might not be the one signing contracts. It might be the one signing investments.