The Dallas Cowboys’ Championship Drought and the Philadelphia Eagles’ Winning Formula

A Painful Contrast for Cowboys Fans For Dallas Cowboys fans hoping their team would finally reach the NFC Championship Game as their Super Bowl drought extends to 30 years, watching the Philadelphia Eagles cruise to their second Lombardi Trophy since 2018 was anything but easy. The stark difference between these two franchises has never been more apparent. While both teams are fierce rivals on the field, their approaches to team-building and long-term success are vastly different.

The Eagles’ Winning Mentality Since 2018, the Eagles have made three Super Bowl appearances, winning twice. This success is a testament to general manager Howie Roseman’s aggressive and strategic roster management. Unlike the Cowboys, who have largely remained stagnant in their team-building philosophy, the Eagles have proven that taking calculated risks can yield championship results.

Following the Eagles’ latest Super Bowl victory, team owner Jeffrey Lurie made it clear what sets them apart. Speaking to Jori Epstein of Yahoo! Sports, he said of Roseman, “He’s not risk-averse. He’s aggressive. That’s what I want.” That statement alone encapsulates the difference in mentality between the Eagles and the Cowboys.

Smart Risk-Taking in Philadelphia Roseman’s success stems from his willingness to make bold moves. He let Pro Bowl running back Miles Sanders walk in free agency, only to sign Saquon Barkley a year later when the right opportunity arose. He took a gamble on linebacker Zach Baun for just $3.5 million, and he wasn’t afraid to break a 20-year trend by drafting cornerback Quinyon Mitchell in the first round. When Cooper DeJean became available in the second round, Roseman made an aggressive trade to secure him.

Even more impressively, Roseman identified under-the-radar talent and maximized their potential. He took a chance on Mekhi Becton when his value was at an all-time low, transitioning him into a quality starter at right guard, a position he had never played before.

Of course, not every gamble has paid off. Bryce Huff, signed as a replacement for Haason Reddick, was a healthy scratch in the Super Bowl. The signing of Devin White also failed to make a significant impact. However, Roseman’s aggressive philosophy ensures that his hits far outweigh his misses. Nakobe Dean, for example, emerged as a strong contributor despite other missteps in free agency.

The Cowboys’ Reluctance to Change Meanwhile, the Cowboys’ biggest acquisitions in 2024 were signing Eric Kendricks and bringing back Ezekiel Elliott. Compared to the Eagles’ dynamic moves, these transactions seem uninspired and unambitious. Cowboys executives often use Dak Prescott’s and CeeDee Lamb’s contracts as an excuse for their conservative approach. However, the Eagles also pay their stars—yet they find ways to manipulate the salary cap and maintain roster flexibility.

Stephen Jones has frequently stated that “the bill will come due” regarding the salary cap. However, the Eagles have mastered the art of deferring financial strain while remaining competitive. Even if their aggressive strategy eventually backfires, they will have multiple Lombardi Trophies to show for it—a reality the Cowboys haven’t experienced since 1995.

The Impact of Ownership and Leadership Cowboys fans have every reason to envy an owner like Jeffrey Lurie, who trusts his general manager and empowers him to make aggressive, strategic decisions. In contrast, Dallas is stuck with Jerry Jones, who refuses to relinquish his role as general manager despite widespread doubts about who truly makes the decisions at The Star. Jones has repeatedly defended his stance by pointing to the fact that he bought the team in 1989—an argument that holds little weight in today’s NFL landscape.

Ownership structure matters. The Washington Commanders’ new ownership group has emphasized hiring the right people and stepping out of the way, a strategy that has historically led to success. The Cowboys, on the other hand, continue to operate like a family-run business rather than a modern, championship-caliber franchise.

Can the Cowboys Change Their Approach? The harsh truth is that winning in the NFL requires adaptability, smart risk-taking, and trust in a true general manager. Without these elements, Dallas will continue to fall short while watching their biggest rival hoist championship trophies. If the Cowboys hope to end their Super Bowl drought, they must break free from outdated philosophies and embrace a more aggressive approach to team-building. Until then, they will remain stuck in the past while teams like the Eagles continue to set the standard for success.