With the 2025 league year approaching, the Dallas Cowboys are facing a financial conundrum regarding quarterback Dak Prescott’s contract. While his deal was structured to provide short-term flexibility, the looming $89.896 million cap hit for 2025 is simply unsustainable. The Cowboys are expected to restructure Prescott’s deal to free up cap space, a move that has become common practice for the organization.

Dallas has long used contract restructures to manipulate the salary cap, and Prescott’s deal is no exception. The Cowboys can convert a large portion of his 2025 salary into a signing bonus, reducing his cap hit to approximately $50-54 million while freeing up roughly $36-40 million in cap space. This strategy allows them to maintain roster flexibility while postponing the financial burden to future years.

NFL insider Mike Fisher of CowboysCountry.com believes this adjustment will happen soon, particularly with free agency set to begin on March 12. “At whatever point the Cowboys wish to do so, they can ‘flip the switch’ on Dak’s existing deal… and gain about $36 to $40 million in cap room,” Fisher reported. Given their offseason needs, it’s unlikely the Cowboys will wait long to execute this move.

The Cowboys have a big decision to make about Dak Prescott

Prescott’s contract isn’t the only one that could be adjusted. The Cowboys could also restructure wide receiver CeeDee Lamb’s deal, potentially freeing up an additional $20 million in cap space. Additionally, if the Cowboys finalize a long-term extension with star defender Micah Parsons, they could create even more financial flexibility, potentially reaching nearly $100 million in available cap room.

However, while restructuring deals provides immediate relief, it comes at a cost. By pushing cap hits into future years, the Cowboys will eventually face a financial reckoning, particularly when Prescott’s time in Dallas comes to an end. If they continue to delay addressing his long-term future, they risk a massive dead cap hit when he eventually departs.

The Cowboys’ front office, led by owner Jerry Jones and COO Stephen Jones, has historically been conservative when it comes to major financial moves. However, with a cap hit nearing $90 million, standing pat simply isn’t an option. If Dallas wants to retain key players and make meaningful additions in free agency, restructuring Prescott’s deal is a necessity.

With free agency just days away, the Cowboys will need to act fast. Whether they restructure Prescott’s deal or negotiate a long-term extension, the decision they make in the coming weeks will shape the team’s financial landscape—and its championship aspirations—for years to come.