The Cowboys have chosen not to negotiate with Pickens on a long-term deal, and that has opened up a whole host of scenarios.
The Dallas Cowboys and paying their star players in a quiet and efficient manner isn't something we often see.
Yes, the Cowboys did that with Javonte Williams and Brandon Aubrey this offseason, but I'm talking about Dak Prescott, CeeDee Lamb, Micah Parsons, and now George Pickens.
With Dallas, oddly, already publicly stating it isn't going to negotiate a long-term deal with Pickens, instead wanting George to play on the franchise tag, that has left many scenarios on the table.
And in the process, it left a lot to the imagination for fans and media, which then creates unnecessary headlines that will dominate the offseason.
But again, that's how Dallas rolls recently.
Many analysts and media personalities believe the 2026 season will be George's last in Dallas, and right now, that scenario could easily come to fruition.
And for Dave Helman of The Athletic, who was a guest on DLLS Cowboys, the whole Pickens situation is rather exhausting.
"If you're convinced you can get two years of George Pickens for $60 million guaranteed dollars and you want to do that, I wouldn't be surprised," Helman said via DLLS Cowboys. "But I just think it's going to lead to some BS, and it's going to lead to George Pickens missing a lot of training camp time, a lot of threats about missing the season opener.
"It just sounds really exhausting. I really wish they could just get it out of the way. It's correct to point out that's not how they do things. It's going to drag out, I would guess, until next spring. I wish that wasn't true, but it feels kind of true."
So, we are already seeing how the uncertainty about Pickens' future is shaping some discussions.
But for me, as far as Pickens missing camp and potentially games, I don't see that happening.
Why? Because he has worked so hard to rebuild his image, if he were to hold out or miss games, the only person who would be suffering in that instance is George, because teams would see that and think he hasn't moved on from the persona that dominated his time in Pittsburgh.
The Cowboys, in theory, could get by with CeeDee Lamb and others (although far from ideal), but I get the sense that a holdout would hurt Pickens more than Dallas.
But Helman is right, it is exhausting.
Either re-sign him, or let him go. Because if things stay as they are, we have an entire season of headlines regarding Pickens' future.
One great game and the "who will come calling or Pickens" or one bad game and the "who will even want Pickens" headlines will be coming out from various national media outlets.
The season hasn't even started yet and I'm tired.
