Jerry Jones faces one of the biggest crossroads in his journey as owner of the Dallas Cowboys. Dak Prescott is entering the final year of his contract and, if the team’s front office doesn’t make a move, the quarterback might say goodbye.

What should have been a smooth negotiation for the franchise quarterback, suddenly became a controversial story in the NFL. It all was triggered by that unexpected playoff loss against the Green Bay Packers.

Now, with almost no leverage left, the Dallas Cowboys have to decide if Prescott is the franchise quarterback who will lead them to the Super Bowl. If they hesitate, it could be too late to keep him.

Will Dak Prescott become a free agent?

Yes. Dak Prescott is set to become a free agent in 2025 and, believe or not, there’s nothing Jerry Jones can do to stop that. Although many fans wondered if the Dallas Cowboys could use a franchise tag on the quarterback, the current quarterback’s contract has a clause to prevent that.

Furthermore, to make things more complicated for Jones, Prescott has a no trade clause in that deal which means the quarterback is in total control of his next destination.

Will Dak Prescott sign a contract extension with the Dallas Cowboys?

If the Dallas Cowboys want to keep Dak Prescott, they’ll have to offer the highest contract in NFL history. A few weeks ago, when Trevor Lawrence signed a five-year, $275 million deal, the landscape totally changed.

Prescott is 30-years old trying to get the biggest payday of his career. Right now, $60 million per year would be the minimum. He put MVP numbers in 2023 and many teams will be ready to make him an offer in 2025.

Will Dak Prescott accept a contract extension from Cowboys?

This is the key part of the equation. The Dallas Cowboys are against the ropes because they have to pay three stars in the next months: Dak Prescott, CeeDee Lamb and Micah Parsons.

It’s seems inevitable that Jerry Jones would lose at least one of them in the near future due to the salary cap. If the Cowboys don’t offer Prescott anything close to his expectations, he could patiently wait until the end of the 2024 season.

Then, he will become the most coveted free agent in the NFL. Considering the current quarterback’s market, and Dak’s possible performance, $60 million annually might be a short number by then. However, anything is possible and Prescott’s biggest enemy could be an injury without guaranteed money in his pocket.