Stephen A. Smith Slams Dak Prescott’s $82M Contract Restructuring: “It’s Overpaying” Amid Playoff Struggles

Stephen A. Smith has once again made waves with his sharp criticism of Dallas Cowboys quarterback Dak Prescott, this time focusing on his substantial contract restructurings. After the quarterback’s recent conversation with Los Angeles Rams owner Stan Kroenke went viral, Smith didn’t hold back in pointing out Prescott’s playoff shortcomings. Now, the ESPN analyst is taking aim at Prescott’s financial situation, calling it an example of the Cowboys overpaying their star quarterback.

A Pattern of Underachievement

In a segment on First Take, Stephen A. Smith delved deep into Prescott’s playoff performance, or lack thereof, over his ten-year career. The Cowboys’ franchise QB has managed just two playoff victories during that time, a stat that Smith argues highlights his inability to deliver when it matters most.

“Two playoff wins in 10 years,” Smith said. “He can ball, but the highest-paid quarterback in the NFL? Hell no.”

Smith’s criticism centers on the fact that while Prescott is one of the highest-paid players in the league, his postseason accomplishments fall short of expectations. Given the Cowboys’ reliance on Prescott for their playoff hopes, the analyst questions whether the franchise is getting its money’s worth.

The $82 Million Question

But Smith’s criticism doesn’t stop at Prescott’s on-field performance. The ESPN commentator also pointed out the Cowboys’ repeated contract restructures, which he believes are signs of financial mismanagement. Over the past five years, Prescott’s contract has been restructured five times, creating $82 million in salary cap space for the team, a move that Smith argues has become a glaring indicator of an overpaid quarterback.

Smith walked through the various restructurings in detail, each move designed to free up cap space but also highlighting the financial burden Prescott places on the team. Here’s a breakdown of the restructurings that Smith pointed out:

• Sept. 7, 2021: $6.25 million of salary converted to bonus, freeing up $5 million in cap room.

• March 8, 2022: $18.4 million converted to a signing bonus, creating $14.4 million in cap space.

• March 10, 2023: $29.2 million converted to a signing bonus, freeing up $22 million.

• March 18, 2024: A $5 million roster bonus turned into a signing bonus, adding two void years and freeing up $4 million.

• March 5, 2025: $45.75 million converted to a signing bonus, creating $36.6 million in cap space.

  

These five moves, totaling $82 million, have allowed the Cowboys to free up significant cap space. However, Smith believes that the frequency of these restructurings reflects poor financial planning. The constant restructuring of Prescott’s deal, Smith argues, reveals that the Cowboys are more focused on creating temporary cap space than on properly structuring long-term contracts that could lead to success on the field.

Overpaying for Underperformance?

For Smith, these contract moves are an obvious indication that the Cowboys are overpaying Prescott. While the franchise has placed a heavy bet on Prescott’s ability to lead them to a Super Bowl, Smith believes that their repeated attempts to restructure his deal suggest that they are trying to make up for the shortcomings in his performance.

“That’s how you know you’re overpaying your quarterback,” Smith argued. “That’s how you know you’re not structuring deals right. That’s how you know you’re too busy with pomp and circumstance and the headlines… more focused on the red carpet than competing for a championship.”

According to Smith, this financial strategy has hampered the Cowboys’ ability to build a team capable of winning a Super Bowl. While other teams are focusing on balancing their roster and maximizing their salary cap, the Cowboys seem to be prioritizing maintaining a big-name quarterback at the cost of long-term team-building.

Impact on Super Bowl Hopes

Smith’s larger point is that the Cowboys’ financial focus on Prescott’s contract makes it harder for the team to surround him with the talent needed to win a championship. As one of the highest-paid quarterbacks in the league, Prescott should be carrying the team to victories in the playoffs. However, with only two postseason wins in his career, many argue that he hasn’t lived up to the contract or the expectations placed on him.

Smith’s perspective resonates with many fans and analysts who question the Cowboys’ decision to make Prescott one of the highest-paid quarterbacks despite his inability to produce in the postseason. While the regular season has seen flashes of brilliance from Prescott, his failure to perform when it counts most has led to increasing frustration from fans and media alike.

A Financial Gamble

In essence, the Cowboys’ ongoing financial commitment to Prescott comes across as a gamble. While the contract restructurings allow the team to create cap space and keep their franchise quarterback under contract, Smith believes that these moves don’t address the fundamental issues facing the team: postseason success and a Super Bowl title. For the Cowboys, maintaining Prescott as one of the highest-paid players in the league without tangible playoff success could ultimately cost them in the long run.

As the Cowboys continue to build their team and attempt to chase a championship, Smith’s commentary on Prescott’s contract will likely resonate with those who believe that the team needs to reassess its financial strategy. The constant restructuring might free up immediate cap space, but as Smith pointed out, it doesn’t guarantee postseason victories or, ultimately, a Super Bowl.

Conclusion: A Call for Change

Stephen A. Smith’s critiques of Dak Prescott’s contract and playoff performances are not just a commentary on the quarterback’s abilities; they are a call for the Cowboys to reconsider how they are structuring their team financially. By focusing so much on maintaining Prescott as one of the highest-paid players in the league, they may be overlooking the bigger picture—building a roster that can actually win the big games.

While Prescott is undoubtedly a talented quarterback, the truth remains that his performance in the postseason has not matched the expectations set by his salary and status. With the Cowboys’ continued restructuring of Prescott’s deal, the question remains whether they can find a way to balance their financial commitment to him with the need to improve the overall team, or if the franchise will continue to gamble on the hope that Prescott can finally deliver a Super Bowl.