With the Cowboys a season away from seeing quarterback Dak Prescott hit the open market, they blinked. As the 2025 league year approaches, they might be dry heaving.

Prescott’s latest contract comes with a cap number of $89.896 million in 2025.

And, yes, that amount can be reduced by (for example) turning most of his 2025 salary into a signing bonus and spreading it over five years. But even if the Cowboys lower his pay to the minimum of $1.255 million and convert the remaining $46.495 into a guaranteed payment, they’re still looking at a $51.445 million cap charge for the coming year.

The move would also jack up each of the next four cap numbers by $9.299 million. Which will set the stage for more restructurings and more can kicking. Whenever the team’s inevitable first year post-Dak arrives, they’ll have to carry a crippling cap charge.

Already, for example, a trade before June 1 would result in a dead-money charge of more than $103 million. One of these years, sooner or later, they’ll end up paying the salary-cap fiddler by having far less money to spend now.

Dak Prescott’s massive 2025 cap hit of nearly $90 million puts the Dallas Cowboys in a tough financial situation. This staggering number is one of the highest cap hits in NFL history, meaning the team will have significantly less flexibility to sign or retain key players. With a salary cap limit that forces teams to carefully manage their finances, committing such a large portion to one player can severely impact roster depth and overall team balance. If left unaddressed, the Cowboys may struggle to build a competitive squad around Prescott.

One of the biggest risks for the Cowboys is the inability to sign or extend crucial playmakers due to cap constraints. With other stars like CeeDee Lamb, Micah Parsons, and Trevon Diggs needing extensions soon, the team must find ways to maneuver around Prescott’s contract. If no adjustments are made, Dallas could be forced to part ways with key talent or make difficult roster cuts. This situation creates tension, as the front office must balance keeping their franchise quarterback while ensuring they can still field a competitive team.

To address this issue, the Cowboys will likely explore options to restructure Prescott’s contract. A contract restructure could help spread out the financial burden over multiple years, reducing the immediate cap hit and creating more spending flexibility. Another option is negotiating a contract extension that lowers the 2025 cap number while securing Prescott for more seasons. However, if an agreement isn’t reached, Dallas might be forced to let him play out his contract and hit free agency, a move that could drastically alter the team’s future.

The biggest question is whether the Cowboys truly view Prescott as their long-term solution. If they do, they’ll likely work hard to secure an extension and restructure the contract. If not, the team could start exploring potential replacements, either through the NFL Draft or free agency. This cap situation makes the 2024 season a defining moment for both Prescott and the Cowboys, as their decisions could reshape the franchise’s trajectory for years to come.