Have Cowboys learned lessons from previous Dak Prescott contract mistakes?

For years, Dak Prescott has been one of the most polarizing figures in the National Football League.

He's alternated great seasons with not-so-good ones, but he's been the best option for the Dallas Cowboys more often than not.

That's why, with a $76 million cap hit in 2027, it's only fair to wonder whether the Cowboys will explore signing him to an extension soon.

According to Sports Illustrated insider Albert Breer, that's pretty much on the table after this season.

The Dallas Cowboys might sign Dak Prescott to an extension soon

"I think it’s fair to believe that the Cowboys should explore that after this season," Breer wrote. "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."

The Cowboys had one of the most explosive offenses in the game in the first year under Brian Schottenheimer's tutelage.

Prescott has a strong chemistry with CeeDee Lamb, and while he lost his mobility after all the injuries, another strong campaign like last season's might be just enough for the Cowboys to give him another long-term deal, even though he'll be 33 when the 2026 season gets underway. 

The Cowboys were uber-aggressive to fix their defense in the offseason. As long as Prescott isn't the reason why they miss the playoffs again, he should be looking at another lucrative deal.