It has been three decades since the Dallas Cowboys last hoisted the Lombardi Trophy. The last time Dallas aced the league was when the roster included stars like Troy Aikman, Emmitt Smith, and Michael Irvin. Looking back at the 1990s Cowboys, Jason Garrett and many others believe the team would have achieved even greater success had those legendary players remained with the franchise a little longer.

“I know it was a young team with a lot of talented players and guys who are committed to winning,” Garrett, former Cowboys head coach, said on The Jim Rome Show. “The work ethic of that group, during that time, was off the charts. And the best players set the standard for the rest of us. I do think the reality of it is, if you remember, the collective bargaining agreement and the players’ association, it’s when free agency and salary cap kicked in. 

“I do think the challenges of being a championship team and maintaining that for a long time were going to be difficult, particularly the outset, as people were trying to figure out how the whole system worked. But having said that, Jimmy [Johnson] was an amazing coach. We had a great group of players. If that group had stayed together, there’s no question in my mind, we would’ve won more Super Bowls.” 

During that era, Hall of Fame offensive lineman Larry Allen and tight end Jay Novacek fortified the team that centered around Aikman, Irvin, and Smith. Meanwhile, Darren Woodson, Charles Haley, and Russell Maryland led the defensive charge. The team packed a punch on both sides of the ball during Johnson’s leadership, especially during its dominant years in the 90s.

But soon, things began to go haywire. Novacek retired in 1997, Irvin ended his career in 2000, and Woodson hung up his cleats four years later. Aikman announced his retirement in 2001, after spending 12 seasons with the Cowboys. They’d all spent multiple seasons with the Cowboys.

And so began the pain of Dallas fans constantly dealing with the weight of not reaching the NFC Championship in the last 30 years.

In the last few years, the Cowboys team was mostly headlined by offensive figures like Dak Prescott. On the defense, the one big star was probably Micah Parsons, who left in 2025. Dallas’ defense was terrifyingly bad last season, despite Prescott and the offense doing their best. The QB finished among the league’s Top 5 in QBR, and wide receiver George Pickens had the third-highest receiving yards total.

Dallas has the talent, but something or the other has held them back from being the competitor they were in the 90s.

Now, the pressure to succeed in the postseason is unlike anything else. The offensive core remains intact in Prescott, Pickens, and CeeDee Lamb. The defense has also been through a remodel under new defensive coordinator Christian Parker. Both sides looked promising in the preseason opener against the Seattle Seahawks. But whether they can replicate this during the regular season is the bigger question.

As the modern Cowboys continue their desperate quest to snap a 30-year championship drought, Garrett’s reflections serve as a reminder of how fleeting NFL dynasties truly are. Of course, Dallas can cherish the glory of the 1990s. But they need to prove themselves in the postseason now.