Stephen “Air Quote” on the Dallas Cowboys Jones has a serious issue with the salary cap.

The Dallas Cowboys, one of the most high-profile and successful franchises in NFL history, are no strangers to the bright lights of national attention. From the team’s storied history to the flamboyant personality of Jerry Jones, the Cowboys have been in the public eye for decades. However, behind the glitz and glamour of America’s Team, there are often financial hurdles that can have a significant impact on the team’s ability to build a championship-contending roster. One of those hurdles? The salary cap, and more specifically, the apparent “serious issue” with managing it that Stephen Jones, Jerry’s son and the Cowboys’ executive vice president of player personnel, has repeatedly faced.

A Complex Legacy of the Jones Family in Dallas

Jerry Jones has been at the helm of the Dallas Cowboys since 1989, taking the reins as both owner and general manager. His bold decision to purchase the franchise, which at the time was struggling, quickly turned the Cowboys into one of the most recognized and valuable sports franchises in the world. Under Jones, the Cowboys experienced significant success, winning three Super Bowls in the 1990s. However, since those glory years, the team has struggled to reclaim the ultimate prize, leading many to question Jones’ long-term approach to team building.

While Jerry Jones has always been in the public eye as the face of the Cowboys, his son Stephen Jones has quietly taken on an increasingly important role within the organization. As the executive vice president of player personnel, Stephen has become the point person for making personnel decisions, including managing the salary cap, which has grown into a thorn in the side of the franchise in recent seasons.

While Stephen’s leadership in Dallas is a key part of the franchise’s day-to-day operations, it’s the salary cap management that has emerged as one of the most contentious aspects of the Jones family’s legacy. Over the past several years, the Cowboys’ financial management, especially their dealings with the salary cap, has come under significant scrutiny.

The Salary Cap Issue: What Went Wrong?

The salary cap in the NFL is designed to ensure that no single team can monopolize talent by spending more than others. Each team is given a maximum amount they can spend on player salaries, which helps to create a level playing field and ensures that teams with strong financial backing don’t simply dominate the league.

For many NFL teams, managing the salary cap is a delicate balancing act. Teams must decide how to allocate resources between a variety of needs: retaining star players, signing key free agents, extending contracts for up-and-coming talent, and building depth across all positions. Stephen Jones and the Cowboys have often faced the dilemma of juggling these responsibilities while attempting to keep the team competitive.

Over the years, there have been several high-profile missteps related to the salary cap that have left Cowboys fans frustrated and wondering if the team’s financial strategy is ultimately hindering their chances of success.

High-Cost Contracts and Long-Term Implications

One of the most glaring issues with the Cowboys’ salary cap has been their tendency to hand out lucrative, long-term contracts to players who have shown flashes of greatness but also come with injury concerns or declining performance. These contracts have, at times, hampered the team’s ability to maintain a balanced roster.

For example, Ezekiel Elliott’s contract extension in 2019 caused significant strain on the Cowboys’ finances. While Elliott was an undeniable talent in his early seasons, his deal, worth a reported $90 million, was a heavy burden as the running back position’s value continued to decrease across the league. Elliott’s performance in subsequent seasons has not matched the expectations of his paycheck, and the Cowboys were eventually forced to part ways with the once-dominant back in 2023, marking a difficult chapter in the team’s financial decisions.

Similarly, the contract given to Dak Prescott, one of the league’s highest-paid quarterbacks, has placed a considerable strain on the Cowboys’ cap. Prescott’s deal, which was worth $160 million over four years, was designed to reward a quarterback who had proven to be a franchise leader. But with Prescott’s salary accounting for a significant portion of the cap, the team found it difficult to build a championship-caliber roster around him.

While Prescott’s talent is undeniable, the financial commitments tied to key positions like quarterback and running back left Dallas with fewer resources to allocate to other positions like the offensive line, secondary, and linebacker corps. This imbalance has prevented the Cowboys from truly competing at the highest level.

Cap Space Manipulation and Dead Money

In addition to handing out oversized contracts, the Cowboys have often resorted to manipulating the salary cap by restructuring contracts. This technique allows teams to convert a portion of a player’s salary into a signing bonus, which lowers their cap hit in the short term but pushes the financial burden further down the line.

While this strategy can provide short-term cap relief, it creates a significant problem known as dead money. Dead money refers to the cap hit that remains on a team’s books after they cut or trade a player. In recent years, the Cowboys have accumulated substantial dead money due to contract restructurings and cuts, further restricting their ability to sign new players or extend key talent.

For example, the Dez Bryant release in 2018 led to significant dead money for the Cowboys, as did the subsequent cut of Tyron Smith (although his injury concerns were largely to blame). These moves left the Cowboys with less financial flexibility, and the team has had to continuously navigate the fallout from such decisions.

While Jerry Jones has often claimed that the Cowboys’ financial situation is manageable, the reality is that the accumulation of dead money and restructuring deals has only compounded their cap issues, making it more difficult to sign impact players to help the team improve.

Stephen Jones’ Role in the Salary Cap Dilemma

As the Cowboys’ executive vice president, Stephen Jones has become the central figure responsible for overseeing the team’s salary cap management. Stephen has largely taken on the role of the team’s financial architect, but he has faced increasing pressure to navigate a situation that many believe is holding the Cowboys back from building a true contender.

In interviews and public statements, Stephen has attempted to remain optimistic about the team’s financial health, but there are growing concerns that his approach to managing the cap has been shortsighted. Some analysts argue that Stephen’s tendency to prioritize short-term success over long-term sustainability has left the Cowboys in a precarious position.

Despite the challenges, Stephen has made some key moves that have helped the Cowboys remain competitive. The team’s decision to draft well, particularly in areas like the defensive line and wide receiver, has paid dividends. The development of players like CeeDee Lamb and Micah Parsons has allowed the Cowboys to remain relevant in the NFC playoff race, despite salary cap challenges.

However, the question remains: can the Cowboys continue to compete with the financial structure they currently have in place? Or will the team be forced into a painful rebuilding phase, as their salary cap issues catch up with them?

Jerry Jones’ Influence: A Complicated Dynamic

While Stephen Jones has taken on a more prominent role in the front office, Jerry Jones’ influence over the team’s finances cannot be understated. As the owner of the Cowboys, Jerry Jones is intimately involved in all major decisions, including those related to the salary cap. It’s widely believed that Jerry’s tendency to prioritize star players and marquee names has led to some of the Cowboys’ financial woes.

For example, Jerry’s desire to keep top players like Elliott and Prescott has sometimes meant making compromises in other areas of the roster. The team has often been forced to “make it work” with the available cap space, leaving little room for other important acquisitions.

The dynamic between father and son has been a subject of much speculation in recent years. While Stephen Jones is often portrayed as a more methodical and financially cautious figure, Jerry Jones is known for his aggressive approach to acquiring top-tier talent and creating a roster that generates fan excitement. This conflict between short-term star power and long-term financial sustainability has created tension within the Cowboys’ organization.

Looking Forward: What Does the Future Hold for the Cowboys?

As the Dallas Cowboys continue to grapple with their salary cap challenges, the path forward seems murky. Will Stephen Jones adjust his approach to roster building, focusing more on maintaining financial flexibility? Or will the Cowboys continue to push the limits of the salary cap in pursuit of short-term success?

The decision to move forward with Dak Prescott as the franchise quarterback will likely be one of the most significant factors in determining the Cowboys’ future financial trajectory. Prescott’s deal continues to be a major factor in the team’s ability to sign additional talent, and his performance will be crucial in determining whether the Cowboys’ investment will ultimately pay off.

Moreover, the Cowboys will need to find ways to balance their roster with rising young stars like Micah Parsons while also navigating aging veterans with large contracts. The upcoming offseason will be critical in shaping the team’s direction.