The Dallas Cowboys are on the verge of a painful milestone—their 30th NFL season since their last Super Bowl victory. The franchise that once epitomized success and dominance in the 1990s has since been unable to return to the NFL’s biggest stage.
Troy Aikman, the legendary quarterback who led the Cowboys to three Super Bowl titles, recently reflected on the prolonged drought, expressing frustration over the team’s inability to reclaim its place at the top of the league.
Troy Aikman on the Cowboys’ Championship Struggles
Aikman, who played a pivotal role in the Cowboys’ dynasty of the 1990s, had every reason to believe that the team’s success would continue beyond their Super Bowl 30 triumph against the Pittsburgh Steelers. However, nearly three decades later, he finds himself sharing the same disappointment as the fans.
Speaking at the 2025 Children’s Cancer Fund Gala in Dallas, the Hall of Famer got candid about the franchise’s struggles:
“I thought we had more in us, and I thought we would be back. Obviously, we weren’t. But not only were we not back, but you know, here we are, almost three decades later, and no one’s been back.”
Aikman emphasized that the Cowboys’ inability to succeed in the postseason has tarnished their legacy:
“I speak for the Cowboys faithful in saying that, you know, it’s been a long time. This is the Dallas Cowboys, an organization with a great history. This team has won a lot of games over the years with a lot of different players, but for whatever reasons, they just haven’t been able to get it done in the postseason. But I don’t think anybody’s happy about that, that that’s been a part of the Cowboys’ legacy and what this franchise has stood for for so many years.”
With each passing year, the pressure on the Cowboys’ front office, coaching staff, and players only intensifies. Fans are eager to see Dallas return to the pinnacle of the NFL, but the road has been filled with disappointment.
Dak Prescott: ‘We’re Pretty Close’ to the Eagles
While the Cowboys struggled in the postseason, their NFC East rivals, the Philadelphia Eagles, soared to their second Super Bowl title in eight seasons, further rubbing salt into the wounds of Cowboys fans.
Despite Philadelphia’s championship success, Cowboys quarterback Dak Prescott remains confident that Dallas isn’t far behind. Speaking at the same gala event, Prescott acknowledged the Eagles’ success but stressed that the gap between the two teams isn’t as large as it seems:
“I feel like we compete with the Eagles and beat them for the most part when we’ve played them. I don’t want to say check the record when the other guy’s holding a trophy right now. So, credit to them. They’ve earned it, and they deserved it, by all means… It’s our turn, and it’s on us.”
Prescott’s optimism is backed by numbers. While the Eagles swept the Cowboys in 2024, the overall head-to-head record between the two teams since 2017 has been close—Dallas leads with nine wins to Philadelphia’s seven.
However, the reality remains that postseason success is what truly defines a franchise. Despite their regular-season dominance over the Eagles, the Cowboys have failed to make it past the divisional round, while their rivals have secured two Lombardi Trophies.
The Road Ahead: Can the Cowboys End Their Playoff Curse?
With a talented roster and a franchise quarterback in Prescott, the Cowboys have the pieces to compete. But as history has shown, regular-season success means little if they can’t translate it into a deep playoff run.
The pressure is mounting, and as the 2025 season approaches, all eyes will be on Jerry Jones, Mike McCarthy, and the entire Cowboys organization to see if they can finally break the cycle of postseason failure.
For the Cowboys and their fans, the message is clear—it’s time to turn potential into championships.
I am a writer with a passion for technology and gaming. I write about a variety of subjects, including Esports, Games, Shows, and Sports. I create engaging and informative content for Hiptoro.