Cowboys' Dak Prescott named among blockbuster contracts teams will regret signing

With all the drama surrounding Micah Parsons, it's easy to forget that Dak Prescott is only heading into the first year of his four-year, $240 million extension signed last offseason with the Dallas Cowboys.

Prescott is under contract through the 2028 season after adding the four years to his deal, which means he will be making an average of $60 million per season into his mid-30s.

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His age is one of the main reasons Bleacher Report's Brad Gagnon says the Cowboys will eventually regret this contract. He also says Prescott's playoff struggles will factor into the team's eventual regret.

"Prescott is now 32, and injuries have cost him large portions of three of the last five seasons. Despite plenty of support, he’s been a part of just two playoff wins in his nine-year NFL career. And yet in 2026 and 2027, his combined salary-cap hit exceeds a ridiculous $142 million." — Gagnon, Bleacher Report

Dallas Cowboys QB Dak Prescott throws the ball at training camp at the River Ridge Fields. | Kirby Lee-Imagn Images

Gagnon says Prescott was able to leverage the deal thanks to his monstrous 2023 campaign, but there could be issues over the next couple of years based on the enormous cap hit in 2026 and 2027. Dallas will either have to do some fancy accounting to keep from blowing up the roster, or force Prescott to play without any help around him — which would contribute to the postseason struggles.

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Of course, moving the money around means Dallas will be taking a cap hit well after Prescott's deal expires, which could also be viewed as a long-term downside of the contract.

That said, if Prescott is able to get past his playoff woes and win a title, there will be no regrets regardless of the financial ramifications.

Dallas Cowboys quarterback Dak Prescott celebrates after a touchdown against the Cleveland Browns at Huntington Bank Field. | Ken Blaze-Imagn Images

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