
If there is one player who knows more than most about dealing with Dallas Cowboys owner Jerry Jones in the contract space, it's Dak Prescott.
Having been franchise-tagged and then having his four-year, $260 million deal done the night before Dallas was set to play in Week 1 against the Cleveland Browns, Dak knows what Pickens is about to go through.
With a clear number in mind for what the Cowboys think Pickens is worth and what George thinks he is worth, where that settles in terms of a proposed new contract is interesting.
Some think a contract of $32 million APY, just short of CeeDee Lamb's, is where it should land. Others think in excess of $35 million could be coming George's way.
But either way, this won't be an easy or quick negotiation, and the longer it drags out, the more likely it is that feelings can get hurt. We saw last offseason with Micah Parsons what can happen when it gets a little personal.
But for Dak, who was speaking at a Children's Cancer Fund event, he's given Pickens some advice.
"George loves football,” Dak said. “That's the one thing about it. I just want him to know, don't change your love for football. Don't get in the business mind of this. You played last year on a one year for not even that much, right? So if you can go 30 [million], whatever it is now, think it's the same thing I got. So, hey, go do it. At the end of the day, bet on yourself.
"He's a hell of a player. Hopefully, we can get him long-term and sign that. But if not, I think the way that he plays the game and the person that he is, he'll be just fine.”
So Dak wants Pickens to bet on himself, just as he did in his contract talks.
Pickens' 2025 season saw him post 1,429 yards and 9 TDs as he became a key weapon for Dak and Brian Schottenheimer.
But that sort of season has come at a price, and the contract saga that is playing out in the media is that price.
Granted, everything Jerry and Stephen Jones have said regarding Pickens this offseason has been glowing, but time will tell if the Cowboys truly value George long-term.
Prescott has given Pickens some sound advice on how to deal with what's coming his way. Let's see if he takes it.