Fired 20 Years Ago: Skip Bayless Rips Into Jerry Jones Over Cowboys' Failure

A veteran NFL analyst has some criticism for Dallas Cowboys owner and general manager, Jerry Jones. Skip Bayless, an avid Cowboys fan, is not happy with the GM, to say the least.
In his recent appearance on The Arena: Gridiron, Bayless criticized Jones' inability to gather a team that could fight for the Super Bowl.
"If I look at 30 years [of] body of work, if Jerry had just been some other owner's general manager, he would have been fired 20 years ago, right? He just would have. He would have 10 years after Troy Aikman, and it'd be like, nah, you're gone."
Skip Bayless is notorious for his harsh takes, but he still has unwavering support for the Dallas Cowboys. The sports media personality is admittedly friends with Jerry Jones and has been a Cowboys fan since he was a kid.
“I have been a lifelong diehard with this team since I was ten years of age," said Bayless.
However, Bayless is irked that the Super Bowl drought is now 30 years long. The Dallas Cowboys last won the Super Bowl in 1996. Since then, they have not even made it to a Super Bowl, let alone won one.
As Bayless has grown up with the team, it is especially hard for him to see his childhood team's downfall.
“Because when you’ve been there through the 90s, and I was there through that dynasty, and if you saw that Netflix documentary, I was all over it. I all but narrated it. So I lived and breathed that.”
Bayless' comments come a few days after Jones told reporters that he is feeling good about his defense after acquiring a few players in free agency.
"I feel very good about it. We have nowhere but up to go on defense. That’s not anyone’s fault at all. But we’re going to almost assuredly be much better."
However, Bayless is not feeling the positivity.
What Grade Did Skip Bayless Give Jerry Jones for His Management?
Although Bayless considers Jones a friend, when it comes to proceedings on the football field, he did not have such kind words for him.
On The Arena: Gridiron show, Bayless talked about being impressed by the Cowboys' status as America’s team, calling it the "most valuable" and "most watched" team in the NFL.
But, where he was rather unimpressed was with Jerry Jones' performance.
"I give Jerry Jones, for the last 30 years, a flat-out F, as in flunk, as in fail,” Bayless declared.
Again, this is in reference to the Cowboys not winning a Super Bowl in 30 years and their poor playoff performance. In the 2024 and 2025 NFL seasons, the Cowboys did not even make it to the playoffs.
The Cowboys are 5-13 in postseason games since their last appearance in an NFC Championship Game and a Super Bowl.
Bayless added that Jones was responsible for it.
"He is the owner and the operator. He is the general manager.”
Maybe a change in the Dallas Cowboys' luck this 2026 season will change Bayless' mind.
What do you think about Bayless' take? Let us know in the comments.
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Written by
Samvruth Raj
Edited by
Sayantan Gayen
