Imagine an NFL team entering the league in 1960, making the playoffs 36 times, winning five of eight Super Bowls it played, but none in the past two decades. This is the story of the Dallas Cowboys. Being one of the most established and dominant NFC teams, the Cowboys have put up phenomenal performances in the past. What might be the reason they are not able to keep up with the other teams?
A group of NFL insiders, including 1977 Eclipse Award for Outstanding Newspaper Writing winner Skip Bayless, shared their perspectives and possible explanations for the problems. Bayless also had a suggestion to help the franchise win its next Super Bowl.
How Skip Bayless Thinks the Dallas Cowboys Can Win a Super Bowl
On “The Arena: Gridiron” podcast, Bayless sat with ex-NFL cornerback Aqib Talib, former NFL coach Jay Gruden, ex-Super Bowl champion T.J. Ward, and social media influencer Kinsey Wolanski to discuss recent player transfers and their takes on the Cowboys.
Bayless said, “What if Howie 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.”
Talib then added to his point, saying, “He hit on Jalen Hurts, man.”
Bayless continued, “He did. And I tweeted in real time, as soon as he took him in the second round, I said, ‘Jalen Hurts will change life in Philadelphia.'”
Gruden supported his statement, saying he remembered. “You did call it, though, Skip. I do remember that. But he got some s*** because they’re saying, why are you taking a quarterback in the second round? You got a quarterback here already,” he said.
Bayless expressed shock at a particular player’s choice of team. Speaking of Dallas Goedert, he said, “And now look. Just when I thought Dallas Goedert was long gone, he got – I don’t know how he did this. I still don’t get why Dallas Goedert would go back to Philadelphia for $3 million less.”
What would happen to the Cowboys and Eagles if Howie Roseman and Jerry Jones switched places? 🤔 pic.twitter.com/xxnyAcMj4P
— The Arena: Gridiron (@ArenaGridiron) March 22, 2026
“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,” Gruden said, highlighting the importance of playing under the right manager.
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Ward, a player who has played for three teams in his career, seconded his motion. He said:
“You want to be in a winning environment. You get a couple of mils, go somewhere else. You lose, and you got to move your whole family. It’s a headache. It ain’t worth the $3 million. I want to be here. I’ve been here my whole career. I know we’re going to be in Super Bowl contention year in and year out. I don’t got to Buffalo or Wisconsin. Just in terms of places to live.”
Wolanski concluded, “Buffalo cold is a different kind of cold.”
