Bulldog Roundup: Will Cowboys regret Dak Prescott's contract extension?

Mississippi State fans will always have fond memories of Dak Prescott, the former Bulldog quarterback that helped put Mississippi State at No.

1 in the first-ever College Football Playoff rankings in 2014.

Dallas Cowboys fans may not end up having as such fond memories.

At least if Bleacher Reports' Brad Gagnon's prediction comes true.

Gagnon listed Prescott's four-year, $240 million signed in 2024 as one of eight NFL contracts teams will eventually regret.

Other players include Pittsburgh's TJ Watt, San Francisco's Brock Purdy, Cincinatti receiver Tee Higgins and Miami's Tua Tagovailoa.

Here's what Gagnon said specifically about Prescott's contract extension: "An ongoing dispute threatened to linger into the final year of Prescotts last deal, and the team probably figured itd be best to keep rolling long-term with a guy who was the MVP runner-up in 2023," he wrote.

"Prescott is now 32, and injuries have cost him large portions of three of the last five seasons.

Despite plenty of support, hes 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." The Cowboys may end up regretting Prescott's extension.

One could even argue, based on comments from owner Jerry Jones , the Cowboys already do regret it.

But if Jones realized he isn't as smart as he thinks he is and stops dragging his feet with giving his best players contract extensions, there'd be fewer chances to have regrets about contracts.

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