Former Cowboys Head Coach Shares Thoughts on Embarrassing Super Bowl Drought

The Dallas Cowboys haven't been to the Super Bowl since the 1995 season, which is surprising to one of their former coaches.

Dallas Cowboys owner Jerry Jones and NBC commentator Jason Garrett speak before the game against the Green Bay Packers. | Jerome Miron-Imagn Images

It's been tough to be a Dallas Cowboys fan over the past 30 years.

A team that was once a dominant dynasty has not advanced beyond the second round of the NFL playoffs since winning the Super Bowl following the 1995 season. Every other NFC team has accomplished this feat, leaving a massive spotlight on the Cowboys every year.

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Former head coach Jason Garrett had a chance in 2014 with one of the more talented rosters led by Tony Romo, DeMarco Murray, Dez Bryant, and Jason Witten, but was unable to get the job done. Since Garrett left in 2019, the story has remained the same, something that surprises Garrett.

“You certainly would think that by now that would happen,” Garrett said via Calvin Watkins of the Dallas Morning News. “We have our stories when we were there as a coaching staff and some close games we played in the divisional round and chances to go to the championship game. But we didn’t get it done, and there’s a bottom line to this. The Cowboys, until they break through, people are still going to be talking about it.”

The Cowboys had three consecutive 12-win campaigns under Mike McCarthy, who replaced Garrett. His lack of playoff success, however, led to his departure. Now, Brian Schottenheimer is at the helm, and he's going to be under pressure to deliver as he enters his second season as the head coach.

Can the Cowboys end the drought in 2026?

Dallas Cowboys head coach Brian Schottenheimer looks on before the game against the New York Giants. | Robert Deutsch-Imagn Images

Asking Dallas to end the drought this coming season will be tough.

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While they do have a dominant offense led by Dak Prescott, their defense has far too many holes to feel confident. That said, they can fill these holes in free agency, as well as the 2026 NFL draft where they have two selections in the first round.

If they can build a defense that can even be average, the offense could be enough for them to end the drought. The question, of course, is whether they have the ability to capitalize.

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