Dak Prescott’s four-year, $240 million contract with the Dallas Cowboys has been named one of the NFL’s worst deals ahead of the 2025 season.

Analysts have criticized the record-breaking extension for its massive financial commitment, with $231 million guaranteed, and the pressure it places on both Prescott and the Cowboys.

The contract, signed just before the 2024 season, made Prescott the highest-paid player in NFL history by annual salary.

While intended to secure stability at quarterback, the deal has drawn scrutiny for its timing and structure. Critics argue that Dallas overpaid compared to more team-friendly deals signed by quarterbacks like Jared Goff and Jordan Love during the same period.

Prescott’s performance has been solid, but his inability to lead Dallas past the divisional round since 1995 has amplified concerns.

Injuries have also limited his availability, with 25 missed games over the past five seasons disrupting the team’s rhythm.

While his leadership and locker-room presence are praised, the lack of postseason success has raised questions about whether the investment can be justified.

The financial implications of the deal are steep, with a projected $74 million cap hit in 2026, potentially hampering Dallas’ ability to build a competitive roster.

With younger, more affordable quarterbacks emerging across the league, Dallas’ reliance on an experienced but injury-prone Prescott has sparked debate about the long-term viability of their strategy.

NFL Expert Names Dallas Cowboys Star Dak Prescott’s Contract As One of the Worst in the League

As it stands, Prescott’s current contract doesn’t really offer Dallas the value for their money. This is detailed more in an analysis by Kristopher Knox for Bleacher Report.

Contract Terms: four years, $240 million with $231 million guaranteed.

The Dallas Cowboys made a few mistakes when it came to Dak Prescott’s 2024 contract extension. For one, they waited until just before the start of the regular season to get it done, which meant waiting until after QBs like Jared Goff and Jordan Love signed their own deals.

Then, Dallas made Prescott the highest-paid player in NFL history by a fairly considerable margin. With a deal worth $60 million annually, Prescott makes at least $5 million more per year than any other player—including quarterbacks like Love, Joe Burrow and Josh Allen.

Despite the criticism, Prescott remains committed to leading Dallas to a long-awaited Super Bowl appearance. The pressure to deliver is immense, as the team’s playoff drought weighs heavily on the franchise’s legacy. For Prescott, the 2025 season represents a pivotal opportunity to prove his worth.

Ultimately, whether the contract is viewed as a costly mistake or a strategic gamble hinges on Prescott’s ability to elevate his game.

The Cowboys’ championship aspirations rest on his shoulders, making the stakes higher than ever.