So many NFL fans had the same reaction to the Dallas Cowboys trading for wide receiver George Pickens. Put simply, it was hard not to recognize that one of the most drama-laden organizations taking on a player who was characterized as a diva in Pittsburgh and that creating endless headlines throughout the season. That was a fair concern, to be clear. However, all the signs with Pickens in Dallas to this point have been overwhelmingly positive. Yet, there is still a major problem looming for the Cowboys when it comes to Pickens.
All indications throughout the summer thus far are that Pickens is everything the Cowboys could've hoped for. He's a perfect complement to CeeDee Lamb in the Dak Prescott-led passing game. Head coach Brian Schottenheimer has praised the receiver's attention in meetings and work ethic. It's all going well. But what hasn't come with all of this is a new deal for Pickens, who is entering the final year of his rookie contract.
To be sure, that's entirely by design. It was reported immediately after the trade that both the Cowboys and Pickens were comfortable playing this year out and then seeing where the market for the wide receiver stands thereafter — and, just as importantly, whether they want him back in Dallas.
At the same time, though, the positivity around Pickens with America's Team right now raises the concern that the Cowboys are currently treading in dangerous waters when it comes to this situation and the potential problems that could arise.
Cowboys could end up back at square one after George Pickens trade
If everything works as planned and Pickens is as good for the Cowboys offense as fans hope, then the outcome of that is the former second-round pick rightfully demanding a substantial free agency payday. That would be exponentially true if the receiver is able to show advancement in his maturity this season as well.
Unfortunately for Jerry Jones and Dallas, that's not really something they can afford. With the massive contracts of Lamb and Prescott on the books and the likely record-setting extension for Micah Parsons forthcoming, the Cowboys aren't in a financial position to be able to give Pickens a deal that would likely clear $25 million in average annual value. Unless they could work some cap sorcery or get Pickens to take a discount, the likeliest outcome is that they'd lose him on the open market.
If that were to happen, then the Cowboys would be right back where they are currently. However, that might actually make the situation even worse moving forward. Pickens himself was seemingly a pivot after not addressing the wide receiver void outside of Lamb in the draft, and that was in a draft class loaded with talent at the position. As the likes of Joseph Hoyt of The Dallas Morning News and Matt Miller of ESPN, among others, have noted, the 2026 NFL Draft is quite weak at receiver, at least coming into the college season. So that avenue might not be an option.
We know that the Cowboys don't have full confidence in the likes of Jalen Tolbert to be a No. 2 option in this offense, otherwise, why would they have aggressively traded for Pickens in the first place? And with scarce options in the draft, Dallas would likely have to run back a similar playbook on the trade market. Because again, much like with Pickens, there's no real path to them signing a free agent of consequence like Terry McLaurin or someone of that ilk.
While it's hard to argue on a direction that both the Cowboys and Pickens agreed upon when it comes to a new contract, the situation undeniably puts Dallas in a future bind. And if they're entering next offseason looking at Lamb and a group that they don't trust with Pickens getting paid by another team, that'll be a lesson they'll hopefully learn from and rectify moving forward.