The Dallas Cowboys’ decision to sign quarterback Dak Prescott to a 4-year, $240 million contract in September 2024 has been labeled one of the worst financial moves in the NFL, according to a recent Bleacher Report analysis by Kristopher Knox. In a list ranking the 10 worst contracts in the league, Prescott’s deal landed at No. 2, trailing only the infamous fully guaranteed 5-year, $230 million contract signed by Cleveland Browns quarterback Deshaun Watson in March 2023, widely regarded as one of the most disastrous contracts in professional sports history.
Knox didn’t hold back in his critique, pointing out that Prescott’s deal makes him the highest-paid player in NFL history at $60 million annually—$5 million more per year than other top-tier quarterbacks like Jordan Love, Joe Burrow, and Josh Allen. “Prescott is an above-average quarterback, but he has never been elite,” Knox wrote on June 12. “There is no scenario, at this stage in his career, that he’s worth $5 million per year more than any other player.”
A Career Crossroads for Prescott
The scrutiny surrounding Prescott’s contract comes at a pivotal moment in his career. In 2023, he enjoyed his best season, earning an NFL All-Pro nod and finishing as runner-up in MVP voting. However, 2024 was a stark contrast, with Prescott playing only eight games due to a hamstring injury and delivering what many consider his most disappointing season yet. This regression has reignited questions about whether the 10-year veteran can lead Dallas to a Super Bowl—a milestone that remains elusive for the Cowboys.
Adding to the pressure, the NFC East has become increasingly competitive. While the Philadelphia Eagles, fresh off a Super Bowl victory, have been a dominant force in the division for years, the emergence of the Washington Commanders poses a new threat. Washington’s quarterback, Jayden Daniels, selected No. 2 overall in the 2024 NFL Draft, had a historic rookie season, potentially the greatest by a quarterback in league history. As a result, Prescott now finds himself arguably the third-best quarterback in his own division, behind Daniels and Philadelphia’s Jalen Hurts.
A Grim Outlook for the Cowboys
The Cowboys’ challenges don’t end with their quarterback’s performance. On the May 29 episode of The Bill Simmons Podcast, The Ringer’s Bill Simmons painted a bleak picture for Dallas, suggesting they could finish dead last in the NFC East in 2025. This scenario isn’t as far-fetched as it might seem. The New York Giants, coming off a 4-13 season in 2024, are poised for improvement with two first-round picks in the 2025 draft: edge rusher Abdul Carter at No. 3 overall and quarterback Jaxson Dart at No. 25 overall.
“So [the Cowboys] are just going into a season knowing you’re number three, and maybe even worse if the Giants are a little bit better right away than people think,” Simmons said during a conversation with Sports Illustrated’s Albert Breer. “So I do not feel good if I’m in Dallas.”
Winning as the Only Solution
For Prescott, the path to silencing critics remains unchanged: win. Despite his lucrative contract, the pressure to deliver on the field has never been higher. The Cowboys’ struggles in 2024, combined with the rise of divisional rivals like the Commanders and the potential resurgence of the Giants, have placed Dallas in a precarious position. If Prescott and the Cowboys can’t turn things around in 2025, the narrative surrounding his historic contract will only grow louder, further cementing its place among the NFL’s most regrettable deals.