Sports media personality Skip Bayless is asking more questions about his favorite football team, the Dallas Cowboys, and particularly the owner and general manager, Jerry Jones.

Earlier last week on The Arena: Gridiron Podcast, Bayless made a bold prediction that comes with a caveat: moving Jerry Jones from his position as the Cowboys' GM.

“What if Howie (Roseman) and Jerry Jones switch places? What do you think would happen to the two franchises? Dallas would win a Super Bowl in two years. With Howie pulling the strings? My God.” 

There are 32 teams in the National Football League. The Dallas Cowboys are the only team that operates differently, where the owner of the franchise is also the general manager. Jerry Jones has held both roles since he bought the Cowboys back in 1989.

The Dallas Cowboys have not won the Super Bowl since 1996, which marks three decades to this day. The quest for the Lombardi Trophy goes on in Arlington, Texas.

Jones would not like to be reminded of that statistic, but for a franchise estimated at roughly $13 billion, per Forbes NFL Team Valuations, it should do better than that. 30 years is a long wait for America’s Team. 

Bayless feels that his favorite football team needs an actual general manager and mentions the Philadelphia Eagles' GM, Howie Roseman.

Roseman has been with the Eagles since 2000 and has held several roles. In 2015, Roseman became Executive Vice President of Football, in addition to his duties as general manager. 

The Eagles have seen success in terms of two Super Bowls in 2017 and 2022 with Roseman as GM. Subsequently, Roseman won the Pro Football Writers Association (PFWA) Executive of the Year in 2017 and 2022. 

Jay Gruden also said on the podcast, “But you said it because of Howie Roseman. He takes care of his players, and he’s going to consistently put you in a position to win games. Guys want to play for that. Guys want to win.” 

Irrespective of trophies, it is still commendable that Jones has held onto the post at 83 years of age. However, Bayless' only regard is the team's success, and he is not afraid of making harsh comments to that end.

What Are Some of the Harsher Comments Made by Skip Bayless?

Skip Bayless is not someone who holds back his feelings, and he does not mince his words. 

"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,” said Bayless.

Skip Bayless considers the Cowboys' general manager a friend but is not happy with how things have played out on the football field. 

“I give Jerry Jones, for the last 30 years, a flat-out F, as in fail,” Bayless said. 

It is clear how Bayless feels about the whole situation with Jones being the one in the driving seat at the Cowboys, but he does not support them at all.

The Cowboys ended their 2025 campaign with a 7-9-1 record and ultimately did not qualify for the playoffs. The fans can only take so much.

What do you think of Bayless' nomination? Let us know in the comments.

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Written by

Samvruth Raj

Edited by

Sayantan Gayen