The Cowboys know exactly what the plan is with Pickens' future.
The Dallas Cowboys and George Pickens were a superb match in 2025.
Given that George wasn't seen as a top receiver in football prior to his move to the Cowboys, with his time in Pittsburgh being rather volatile, Dallas took a chance.
Of course, we should note that not many other teams were banging down Pittsburgh's door to sign Pickens. Dallas did, and it was rewarded.
A Pro Bowl season from Pickens saw him become one of Dak Prescott's best weapons on an offense that also had CeeDee Lamb. That tells you all you need to know.
Pickens' 1,429 yards and 9 TDs from 93 receptions were all career-highs as he put his turbulent time in Pittsburgh behind him.
But now, due to his superb 2025 season, the time has come to pay him.
Dallas slapped the franchise tag on George, keeping him a Cowboy for at least 2026, but the goal is to sign him to a long-term deal.
And for Cowboys COO Stephen Jones, he was refreshingly self-aware of where the team is regarding George and his future.
"The difficult thing, which everybody sees, is when we are already paying one of the best receivers, if not the best, in CeeDee Lamb at the very top of the market, then obviously the performance George had last year, you can imagine what his expectation is," Jones said on the Rich Eisen Show.
"So that's a challenge, we readily admit that. At the same time, we also know and found out what two premier receivers can do for an offense. Especially if you put them with a quarterback like Dak Prescott."
So Dallas knows full well what Pickens is expecting in terms of a long-term contract, and in truth, the front office should have been prepared for this when they traded for him.
Plus, the Cowboys know what Pickens was able to do in the offense under Brian Schottenheimer last year, and one can safely say that Dallas is easily a playoff team and maybe more if the defense gets fixed.
But the Cowboys know where they stand with Pickens. They know what it will take to retain him long-term. And they know what it will mean if he is a Cowboy in 2026.
Now, let's see if this situation can avoid becoming another Micah Parsons saga.