BREAKING : Dak Prescott singled out as one of the Dallas Cowboys’ worst decisions ever made

Dak Prescott singled out as one of the Dallas Cowboys' worst decisions ever made

As attention around the Dallas Cowboys centers on linebacker Micah Parsons, the organization also faces potential long-term consequences from quarterback Dak Prescott‘s contract extension.

Prescott is set to begin the first season of a four-year, $240 million extension signed in 2024, keeping him under contract through 2028.

The agreement carries an average annual value of $60 million and will significantly impact the team’s salary cap in future seasons.

Prescott‘s age and playoff track record are central concerns. He will be 32 entering the 2025 NFL season and has missed substantial time due to injuries in three of the last five seasons.

Despite playing on a roster with considerable talent, Prescott has led the Cowboys to just two playoff victories over his nine-year career.

There are doubts over the deal

Bleacher Report’s Brad Gagnon recently outlined why Dallas may ultimately regret the deal. “Prescott is now 32, and injuries have cost him large portions of three of the last five seasons,” Gagnon wrote.

“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.”

While the extension was largely influenced by Prescott‘s strong 2023 campaign, Gagnon notes that the contract’s structure could limit roster-building flexibility in the near future.

The Cowboys will likely need to restructure current deals or reallocate cap space, which could result in reduced on-field support for Prescott or delayed financial penalties beyond the life of the contract.

This scenario presents two unfavorable outcomes: weakening the supporting cast around the quarterback or incurring significant dead cap charges after Prescott‘s departure. Both could undermine the franchise’s competitiveness.

However, should Prescott lead the team to a championship, the contract’s cost may be viewed as justified.

Without that success, the financial burden associated with his extension could impede the Cowboys‘ long-term development.

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