Cowboys’ Trade for George Pickens Rated as One of the Riskiest Offseason Moves — Here’s Why

Dallas acquired Pickens for a relatively modest price—sending a 2026 third-round pick and a 2027 fifth-round pick to Pittsburgh while receiving a 2027 sixth-round pick in return. Financially, he remains affordable in the final year of his rookie contract, but his looming free agency in 2026 presents a challenge. If Pickens excels this season, Dallas risks losing him to a lucrative deal with another team.

Head coach Brian Schottenheimer faces the task of managing Pickens’ temperament and integrating him into the team’s offensive system quickly. The team is coming off a disappointing 7-10 season, and pressure to deliver immediate results adds urgency to the move. While Pickens’ upside is undeniable, his potential to disrupt team chemistry cannot be ignored.

NFL Analysis Says Dallas Cowboys’ George Pickens Trade Was a Risky Offseason Move

Dallas’ decision to trade for Pickens was a risky move done during the offseason. This is detailed more in an analysis by Kristopher Knox for Bleacher Report.

If a seasoned head coach like Tomlin can’t corral Pickens, the receiver could become a real problem for Schottenheimer.

Even if Pickens shows maturity in Dallas, complements Lamb perfectly and returns to being a 1,000-yard receiver, he’s bringing a risk factor. That’s because the Cowboys traded for Pickens as he was entering a contract year.

If Pickens flops, the Cowboys offense may disappoint. If he truly shines, he could price himself out in 2026 free agency—if and when Dallas extends Parsons, it will have three players earning at least $34 million annually.

This trade reflects Dallas’ ongoing pattern of high-risk, high-reward decisions in roster building. The Cowboys are betting on Pickens to elevate their offensive production, but the stakes are high. If he falters, the move could backfire and further hinder the team’s playoff aspirations.

Ultimately, the success of this trade depends on Pickens’ ability to mature and perform at a high level. For Dallas, the gamble underscores their commitment to taking bold steps in pursuit of a return to NFL relevance.