Cowboys legend unhappy about team's lack of playoff, Super Bowl success

It's been rough sledding for the Dallas Cowboys over the past three decades, with the team's Super Bowl drought extending to 29 years. To make matters worse, Cowboys Nation had to watch the Philadelphia Eagles hoist the Lombardi Trophy this season.

Troy Aikman, who quarterbacked the legendary Cowboys team of the 1990s, recently sounded off on the team's lack of postseason success since he was leading the team to victory at Super Bowl XXX in 1996.

Aikman appeared at the Children’s Cancer Fund event in Dallas with current Cowboys signal-caller Dak Prescott when he shared his thoughts.

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"I thought we had more in us and I thought we would be back. Obviously, we weren't," Aikman said, as transcribed by Sports Illustrated. "But not only were we not back, but here we are almost three decades later and no one has been back. I think I speak for the Cowboys faithful in saying that it's been a long time and this is the Dallas Cowboys.

Troy Aikman on the Dallas Cowboys not being back to the Super Bowl in almost 30 years pic.twitter.com/2S76alig2X
— Jon Machota (@jonmachota) February 11, 2025

"It's an organization that has had a great history and 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. I don't think anybody is happy about that."

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Since Aikman and the Cowboys defeated the Pittsburgh Steelers, 27-17, to win the fifth Super Bowl in franchise history, the team has played in only 18 postseason games.

Dallas Cowboys quarterback Troy Aikman holds the Vince Lombardi Trophy. | James D. Smith-Imagn Images

They have failed to return to the NFC Championship Game, going 5-13 over that timespan.

With a new regime led by Brian Schottenheimer and heavy investments in star players like Prescott and wide receiver CeeDee Lamb, the Cowboys are hoping they can finally turn the corner. There is still a lot of work to do in Big D, but the fans and team legends are ready.

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