The Pittsburgh Steelers' decision to trade George Pickens to the Dallas Cowboys this past offseason is starting to look like one of those moves that haunts a franchise for years. And now, with Pickens thriving in Dallas, the contrast between what he’s become and what he never quite got the chance to be in Pittsburgh is impossible to ignore.
Let’s start with what’s happening in Dallas. Pickens is still a work in progress-he was benched for the opening drive of a recent game-but the Cowboys have found a way to manage the full Pickens package.
That includes the undeniable talent and the sometimes unpredictable personality. After that brief benching?
He responded with nine catches for 144 yards and a touchdown. That’s the kind of bounce-back performance that tells you everything you need to know about his ceiling-and how Dallas is tapping into it.
The Cowboys aren’t trying to change who Pickens is. They’re embracing him.
That’s a key difference. In Pittsburgh, the focus seemed to be more about managing the “character concerns” than maximizing the player.
In Dallas, they’ve flipped that script. First-year offensive coordinator Brian Schottenheimer connected with Pickens early, and that relationship has been a stabilizing force.
Sure, there are still some bumps-tardiness being one of them-but the Cowboys aren’t letting that overshadow what he brings to the field. As one team source put it, Pickens “might miss a team bus or be late on occasion,” but the team isn’t making a federal case out of it.
They’ve fined him when necessary, but more importantly, they’ve acknowledged that he’s been a hard worker and accountable. That’s what matters most in a locker room: effort, production, and trust.
That kind of flexibility-and maturity from the coaching staff-has paid off. The Cowboys are getting everything the Steelers hoped for when they drafted Pickens: a dynamic playmaker who can take over a game.
And now, there’s talk of a contract extension that could exceed $30 million annually. If that deal gets done, it won’t just be a win for the Cowboys-it’ll be a glaring reminder for Pittsburgh of what they let slip away.
So how did we get here? Part of the answer lies under center.
In Pittsburgh, Pickens never had consistent quarterback play. Over three seasons, he caught passes from five different starters: Kenny Pickett, Mitchell Trubisky, Mason Rudolph, Russell Wilson, and Justin Fields.
That kind of instability stunts development-especially for a young, rhythm-based receiver like Pickens. You can’t build chemistry if the quarterback carousel never stops spinning.
Enter Dak Prescott. The Cowboys’ veteran quarterback has brought a level of stability and leadership that Pickens never experienced in Pittsburgh.
According to those close to the team, Pickens respects Prescott, and that mutual respect has been a game-changer. Prescott’s steady presence on and off the field has helped unlock a version of Pickens that the Steelers never got to see.
It’s not just about the quarterback play, though. It’s about culture.
The Cowboys have created an environment where Pickens can be himself-quirks and all-while still being held to a standard. That balance is tough to strike, but when it works, it unlocks something special.
For the Steelers, this is a tough pill to swallow. They drafted Pickens, developed him, and ultimately gave up on him before figuring out how to make it all work. Now, they’re watching from afar as the Cowboys reap the benefits of a player they couldn’t quite figure out.
And if that extension does come through? It won’t just be a payday for Pickens. It’ll be a statement from Dallas-and a painful reminder for Pittsburgh of what might’ve been.