Tuesday marked one week until the 2025 NFL trade deadline, and it is going to be interesting to see what the Dallas Cowboys choose to do (or not do for that matter). A topic of discussion as of late involving the upcoming deadline is wide receiver George Pickens.
The Cowboys acquired Pickens in the offseason for what was effectively their 2026 third-round pick. An argument could be made that the Pittsburgh Steelers feel some remorse about moving someone as talented as Pickens is proving once again to be, but the subject of remorse is sort of why we are chatting today.
Ed Werder reported on Tuesday that Dallas has yet to have any conversations with Pickens about a potential extension with the club.
Pickens has been a revelation of a player for the Cowboys. They would be significantly worse without him. An ideal world is one where he is catching passes from Dak Prescott and opposite of CeeDee Lamb for the foreseeable future.
Context matters, though. Importantly, context about how the Cowboys have handled contract extensions matters. Context about who the team is in our current moment carries great weight as well.
Dallas has handled extension talks with their superstars in rather poor fashion over the last few years. Dak Prescott (on multiple instances), and CeeDee Lamb, had to go through the ringer to get their deals and they came at the eleventh hour. Micah Parsons went through a similar process and the situation turned so contentious that the Cowboys traded him to the Green Bay Packers. In the team’s defense, they did immediately get long-term deals done with DaRon Bland, Tyler Smith, and Hunter Luepke following the Parsons trade, but who they have been for about a half decade now matters with Pickens.
We know that the Cowboys are a middling team in 2025 and are unlikely to win the Super Bowl. Given the fact that Pickens is in a contract year at the moment and the trade deadline is approaching, the idea of trading him away and cashing out merits discussion. This is particularly true if you expect the Cowboys to handle extension talks with him with their typical shenanigans.
There is nothing stopping the Cowboys from getting an extension done with Pickens now (speaking matter of factly). It makes sense that Pickens would want to wait at this point, given the success he has had so far this season, and use a potential open market to his advantage. This is another situation (like Prescott, Lamb and Parsons) where the Cowboys allowed leverage to slip away from them into the hands of their players.
None of this is an advocating for trading Pickens. (I want the opposite personally). But what most of us want, ultimately, is for the Cowboys to have some sort of plan. Their lack of a true North Star has burned them many times in the last few years. In the same offseason that they traded for Pickens in a win-now sort of move, they traded away Parsons, putting the future more in focus. These things do not serve the same end goal.
That is what matters most here. A plan has to be in place. If it is and they follow it, even if it is a plan we disagree with, then at the very least they are focusing all of their efforts and energy on one singular idea.
What do you think that idea is, if we assume they are doing so?
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