If the Cowboys fail to sign Dak Prescott to a long-term extension, the QB will enter free agency in 2025.

The Dallas Cowboys had one of the more underwhelming playoff runs in the NFL this season. The team ended its regular season on a high note, winning the NFC East, but collapsed in the Wild Card Round. Dak Prescott, the team’s quarterback, had an MVP-caliber season as he finished among the top-five candidates in the MVP voting. This off-season is significantly important to him because it marks the last year of his contract with the Cowboys.

Speculations pointed out the fact that Jerry Jones would rush to get a deal done with Dak Prescott this season thereby securing his future as a Cowboy. However, that may not be the case.

His 73-41 regular season record and 2-5 playoff record is the reason for the complication. Jones further stated to the Fort-Worth Telegram that,

Dak has done nothing to change my mind about any promise for the future.

If both sides fail to negotiate an extension, Dak Prescott will earn $34 million as per the terms of his existing contract, but it will result in a $59.5 million cap hit to the team. Jerry Jones has faith in his quarterback, but he did not mention anything about having extension talks with him anytime soon.

Dak Prescott is expecting a huge contract that pays him close to $50-60 million annually

Prescott is the key piece upon whom the team’s success is dependent on. Continually laying emphasis on the point that unless Prescott has a solid performance in the playoffs, the Cowboys will continue to fall short of the playoffs, Jones stated,

I think I've said in the deal that we will go as far as Dak takes us in the playoffs. Remember that. We will go as far as Dak takes us, and that is how far we went. So my point is, that doesn't change a thing. We'll go as far as Dak Takes us.

Dak Prescott (via Imago)
During the regular season, Stephen Jones had revealed that the team’s top priority was to keep Dak Prescott with the team for a long term in the off-season. But even after a blowout loss to the Packers, Jerry Jones does not have any second thoughts about doing so. The owner described himself as being “unequivocal about all of the contracts,” that the team has pending in the off-season.

His faith in Dak Prescott was further solidified when he stated:

I said we see a picture of him (Prescott) going forward for many years, that's alive and well. Yes, we sure do, but we've got a lot of contracts to address.

The team wants to hold on to Prescott but at the same time needs to consider the contracts of their other stars. Jones will have to balance signing Micah Parsons and CeeDee Lamb to big contracts in the off-season as well. If the team fails to offer Prescott an extension, then the QB will enter free agency in 2025.