The last time the Dallas Cowboys won a Super Bowl was in 1996. Back then, Dak Prescott was just a two-year-old boy. Cut to 2025, their wait for another Super Bowl is nearing three decades. In 2024, Jerry Jones entrusted Prescott to be the face of the franchise, awarding him a four-year, $240 million extension. This made him the highest-paid QB in terms of AAV (Average Annual Value). And Cowboys fans are starting to take issue with this.
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With that contract came a setback in the name of cap space. Indeed, the Cowboys restructured Dak’s deal to reduce the impact, bringing the cap hit down to $53 million post-restructure instead of the original $89.9 million. Still, not everyone believes Prescott’s high-paying contract was a smart move, especially when you consider how other top QBs have their deals structured.
Their very own NFC rivals, the Philadelphia Eagles, structured Jalen Hurts’ 2023 contract (five years, $255 million) in a way that leaves their cap hit at just $21.3 million in 2025, a much more manageable figure for a team with a franchise QB.
Additionally, this financial strain has also limited the Cowboys’ ability to sign key players in free agency, and fans haven’t held back. Many took to X to share their honest reactions, questioning whether Prescott was overpaid and venting their frustration with the team’s financial decisions.
This fan openly admitted that Dak Prescott had one of the worst contracts in NFL history.
Daks contract is one of the worst in NFL history
— 🦅Coop〽️ (@QuinyonClamps) March 21, 2025
Another fan complained that the Cowboys are grossly mismanaged by their owner, Jerry Jones.
This is why the Cowboys can’t win, their franchise is grossly mismanaged. pic.twitter.com/QytGbQqF4u
— just1n (@just1nvest) March 21, 2025
Meanwhile, this user felt that Dak wouldn’t care, perhaps because of the huge income offered by the contract.
Dak don't care
— Harry Berries (@MrHarryBerries) March 21, 2025
Another NFL fan applauded Jalen Hurts for allowing the Eagles to acquire new players by compromising on his contract.
Jalen hurts deserves alot of credit for this bc he prioritizes team and winning over payouts
— BlitzkriegCW04 (@cwhistorynerd) March 21, 2025
Several users also pointed out that Hurts has reached the Super Bowl twice in the last three years and even won once. In comparison, Dak Prescott has a 2-5 playoff record in his career, and he has never been to a Super Bowl.
But beyond the Dak vs. Hurts comparison, another key difference between the Eagles and the Cowboys lies in how each team is managed. For instance, Eagles GM Howie Roseman has received praise for his bold moves, including bringing in Saquon Barkley for one year and building a Super Bowl-winning roster. Meanwhile, Cowboys GM Jerry Jones has faced criticism for his reluctance to sign new players.
However, the billionaire owner reiterated that the Cowboys will approach the 2025 free agency and Draft with “quiet aggression” to acquire some new talent. As it stands, beyond Prescott’s hefty cap hit, the Cowboys’ other major cap burdens are Micah Parsons ($24M), Terence Steele ($18M), and CeeDee Lamb ($15M).
In comparison, the Eagles’ core players like A.J. Brown and Lane Johnson each have cap hits of around $18M, while Jordan Mailata sits at $16M. However, the difference is that the Eagles have already built a solid core, giving them the flexibility to manage their cap space more effectively.
As Prescott gears up for the 2025 season after undergoing surgery, he knows the pressure is huge this year. Another subpar performance won’t be tolerated by Cowboys fans anymore. Especially with the Super Bowl drought nearing three decades.