Cowboys Gamble on Talent, Trouble with George Pickens Trade

The Dallas Cowboys are rolling the dice. They’ve acquired wide receiver George Pickens from the Pittsburgh Steelers, a move that carries significant risk alongside the potential reward. The immediate reaction? "Good luck with that, Cowboys. You’re going to need it."

Pickens possesses undeniable, world-class talent. His speed, brilliance, and ability to make spectacular catches are evident. However, he also brings a world-class headache. He’s a pain in the backside, a player the Steelers ultimately couldn’t fully manage. The question is, if Mike Tomlin, a coach renowned for his player management skills, couldn’t unlock Pickens’ full potential and maturity, how will the Cowboys fare?

This isn’t to paint Pickens as a villain. He’s not an Antonio Brown-level disruption. However, he demonstrably presented problems in Pittsburgh, issues the Steelers coaching staff struggled to resolve. The core of these problems stems from immaturity and selfishness, traits that, arguably, have plagued wide receivers since the dawn of football, and traits that Pickens seems to possess in abundance.

Reports from Pittsburgh paint a picture of a player frequently on the edge. Pickens’ Steelers teammates reportedly had to physically restrain him on the sidelines during multiple games. He engaged in heated shouting matches with fans. The NFL has fined him repeatedly for unsportsmanlike conduct, including incidents stemming from a game against the Cincinnati Bengals last year. He allegedly arrived late to the Steelers’ Week 17 matchup against the Kansas City Chiefs.

Tomlin himself addressed Pickens’ behavior, stating after the Bengals game, "He’s just got to grow up, man. This is an emotional game, man. These divisional games are big. He’s got a target on his back because he’s George; he understands that. But he’s got to grow up. He’s got to grow up in a hurry." At the end-of-season press conference, Tomlin conceded, "There’s certainly obviously more room for growth there. I think he covered some ground in 2024, but there’s certainly a heck of a lot more ground to be covered, and we’ll see where it leaves us." It ultimately left them without him.

Former All-Pro receiver Chad Johnson claimed in February, after speaking with Pickens, that the Steelers wouldn’t face further issues with him. "I guarantee you won’t have any problems out of him no more," Johnson asserted. "I done had that conversation with him. I guarantee you, and I don’t want to sit here and talk about what we talked about, but I told him, ‘Listen, that window of opportunity? That [expletive] shrink real fast now. It don’t matter how good you are, and I’ll use your line, ‘They’ll tolerate you until they can replace you.’" The question now is whether Johnson’s guarantee is transferable to Dallas.

The Steelers will likely maintain a professional stance regarding the trade and avoid publicly criticizing Pickens. However, the reported compensation – a third-round pick as the core of the deal – seems relatively light for a player of Pickens’ caliber. This suggests the trade was less about maximizing value and more about the Steelers reaching their breaking point with Pickens’ behavior.

From the Cowboys’ perspective, the risk is understandable. They’re looking at a shifting NFC landscape. The Philadelphia Eagles are positioned to contend for multiple Super Bowls. The Washington Commanders are emerging as a potent young franchise. The Cowboys, a middle-of-the-pack team at best, felt a need to make a splash, particularly after a relatively quiet offseason. Hence, the gamble on Pickens.

The Cowboys’ thought process is likely tied to Pickens’ untapped potential. They’re envisioning a scenario where, with a change of scenery and a strong supporting cast, he could unlock his full potential. They may be asking themselves the same questions Chad Johnson posed: If Pickens had the opportunities given to Ja’Marr Chase in Cincinnati or Justin Jefferson in Minnesota, what would his numbers look like?

The Cowboys are betting that a change of scenery, a different coaching staff, and a more mature locker room can help Pickens channel his energy and talent in a positive direction.

There is one major element of hope for the Cowboys: CeeDee Lamb. Lamb is widely regarded as a consummate professional and the undisputed leader in the Dallas locker room. The expectation is that Pickens will not act around Lamb as he did in Pittsburgh. Hopefully. Probably. Maybe.

The success of this trade hinges on whether the Cowboys can harness Pickens’ immense talent while mitigating his behavioral issues. It’s a high-risk, high-reward move that could either propel the Cowboys to contender status or further contribute to their existing dysfunction. Good luck, Dallas. You’re definitely going to need it. Only time will tell if this gamble will pay off or backfire spectacularly. The Cowboys are betting that the upside outweighs the downside, a gamble that could define their season, and perhaps, their future.