The Dallas Cowboys, one of the most successful franchises in any sport, have five Super Bowl titles to their name. However, they haven’t won or been to a Super Bowl since 1996. Despite not reaching the Super Bowl in nearly 30 years, fans remain optimistic about Dallas’ chances of reaching the big game each season.
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This offseason, the Cowboys have been aggressive in free agency, the draft, and the trade block. Early Wednesday morning, they acquired Pittsburgh Steelers wide receiver George Pickens. Dallas sent a third and fifth-round pick in 2026 for Pickens and a 2026 sixth-round pick.
Notably, lifelong Cowboys fan and sports personality Skip Bayless reacted to the team’s move to acquire Pickens on The Skip Bayless Show. He liked owner Jerry Jones’ move to acquire the talented receiver, but still has glowing concerns about the running back room and quarterback Dak Prescott in the postseason.
Bayless also thinks Dallas should be a darkhorse playoff team, but admitted the move shouldn’t necessarily view them as Super Bowl contenders.
“I think it puts us back on the NFC East map,” said Bayless. “I think we at least have a chance that I did not think we have. I still don’t love our running back situation, I still don’t think our offensive line will be great. You know how I feel about Dak Prescott in the playoff, he’s 2-5 in the postseason, so, there’s no ‘Super Bowl here we come’”, he explained.
While Bayless is known for usually bashing Jones’ and the Cowboys’ decisions, he gave credit where it is due and applauded the billionaire owner for making a ‘plunge’ by adding Pickens.
“Finally, Jerry Jones just plunged,” Bayless said. “It’s been so long since Jerry Jones plunged in a draft, went high-risk high-reward in free agency, high-risk high-reward in he just plunged for George Pickens. I give Jerry Jones the highest marks for just trying here,” Skip outlined.
For the Cowboys fans, Pickens is for sure a big addition by the Cowboys. They haven’t had a reliable WR2 in awhile, and Pickens is a very good No.2 option. With teams zeroing in on CeeDee Lamb, it could even create more opportunities for Pickens to shine in his new role. In his three-year career, Pickens has 174 catches for 2,841 yards, and 12 receiving touchdowns.
Notably, Dallas has added a ton of players through free agency/trade this offseason. And if things click with Prescott having a big year, they could have a chance at making a deep playoff run.
