They say good things take time, and George Pickens’ arrival in Dallas might just be proof of that. After spending the entire offseason and the 2025 NFL Draft without addressing their glaring need for a WR2, the Cowboys have finally made one of their biggest offseason moves by trading for the former Steelers wideout. Naturally, everyone in the Big D is stoked.
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The unexpected trade has the potential to reshape their receiving corps, and the idea of pairing Pickens with CeeDee Lamb to form one of the league’s most dynamic duos is genuinely exciting. The projections back that up, too.
While Pickens’ 2024 season was disrupted by injuries, his 2023 campaign certainly showcased the elite ceiling he brings to the table. That year, he racked up 1,140 receiving yards and led the entire NFL with 18.1 yards per reception — a big-play threat capable of stretching defenses and flipping field position in an instant.
But questions linger — not about Pickens’ talent, but whether his personality fits within the Cowboys’ often chaotic culture. While most analysts have chosen to stay optimistic, Colin Cowherd isn’t convinced that George Pickens will be a seamless fit in Dallas.
On an episode of The Herd, Cowherd didn’t sugarcoat his concerns, noting that the Pickens-Cowboys marriage can only survive because of one player: “It can only work because of Dak Prescott. Dak Prescott’s temperament and maturity. He’s dealt with Jerry’s ego and Ezekiel Elliott’s nonsense.”
The analyst, of course, took a jab at Elliott for prematurely ending his 2024 campaign with the Cowboys in pursuit of greener pastures.
Still, it was Cowherd’s way of tipping his hat to Prescott — framing him as the Cowboys’ emotional stabilizer, the one who has quietly managed the off-field drama and front office interference that has defined Dallas in recent years. Now, that same leadership will be tested again because George Pickens arrives with not just potential, but baggage.
For those out of context, Pickens’ time in Pittsburgh was marked by emotional outbursts and reported friction with teammates and fans. At one point, Steelers head coach Mike Tomlin publicly acknowledged that Pickens needed to “mature” if he wanted to reach his full potential.
“Dallas right now is the land of misfit boys.”@ColinCowherd sounds off on the Cowboys trading for George Pickens. pic.twitter.com/YouALnhOhr
— Herd w/Colin Cowherd (@TheHerd) May 7, 2025
Hence, the veteran analyst believes that the structure, or lack thereof, in Dallas could make this move risky. “The Cowboys don’t have a great culture,” he said. “This is a volatile, immature wide receiver who’s going to want the ball and is not going to love CeeDee Lamb getting 12 targets, and he gets 4 on certain Sundays.”
To emphasize the point, Cowherd referenced two high-maintenance receivers who found success in highly structured environments: Randy Moss in New England under Belichick and A.J. Brown in Philadelphia under a strong front office.
“The opportunity and chance for mayhem is through the roof… Right now, the Cowboys are the land of the misfit boys,” Cowherd prodded on, summing up his broader concern.
Even so, there’s undeniable upside. With Pickens in a new environment and Dak Prescott coming off another solid campaign, both have something to prove. New head coach Brian Schottenheimer now has the pieces for a more vertical offense — and if Pickens buys in, the move could pay off in a major way.
But as Cowherd made clear, for that to happen, it’ll take more than raw talent. It’ll take maturity, accountability, and a quarterback capable of weathering the storm.
