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Dak Prescott #4 of the Dallas Cowboys

Such is the way of the NFL that it’s never long after a player signs on to a big new contract, that they’re eligible to have that contract reworked or extended, and and all the rumors, speculation and nonsense that came with the last version of the deal is repeated again. So if it seems like it has not been a long time since Cowboys star Dak Prescott signed his previous new big deal, you are right–it was just ahead of Week 1 in 2024 that Prescott agreed to the four-year, $240 million contract on which he is currently playing.

One problem for the Cowboys is that they have restructured Prescott’s deal twice already, pushing significant chunks of money into the future–according to Spotrac, Prescott is owed $76 million next year and $86 million the following year. Eventually, the Cowboys will need to press that into another new deal for Prescott, and has they have found, the longer they wait, the closer they get to actually needing to pay Prescott $86 million (or more) for one season.

That saps the team’s leverage. So, in what would be an unusual move for the Cowboys, the team is being advised to–gasp!–actually get ahead of a star-contract negotiation before it reaches the end of the line.

Cowboys ‘Should Explore’ New Contract

That was the notion from NFL insider Albert Breer when asked, by Brandon Loree of the Cowboys site Blogging the Boys, what should be done with Prescott’s contract.

Wrote Breer: “I think it’s fair to believe that the Cowboys should explore that after this season. They’re still paying a price for waiting as long as they did on Prescott in the first place, all the way back in 2020 and ’21, in the residual leverage the quarterback can constantly wield.

“Waiting cost them then, and waiting until they were into Week 1 of a contract year again in ’24 cost them, so it would make sense to try to get ahead of this one in ’27, with two years left on the deal he signed two years ago.”

Dak Prescott Still a Top-of-the-Market QB

There is no doubt that Prescott is still at the top of his game. In 2025, he was coming off a year in which he suffered a nasty hamstring injury and missed nine games, but responded with 4,552 yards passing–second-most of his career–and a league-high 404 completions. Pro Football Focus rated him the No. 5 overall quarterback in the NFL last season.

He is getting older, but he will be 33 when this season begins and still will be worthy of a top-of-the market new contract. If the Cowboys can get the timing right and get a new deal done without the kind of brinksmanship used in the past, they can fold some of Prescott’s old money into the new deal, kicking a bit more of it farther out.

There will be health concerns, because Prescott has missed at least five games with injuries in three of the past six years. But assuming Prescott does not get hurt in the near future, a new deal should be in the works sooner rather than later.