The Dallas Cowboys’ contract extension storyline has followed the organization in every season over the last several years. Dak Prescott, Ezekiel Elliott, CeeDee Lamb, and even Dez Bryant have each had their own controversial negotiations.
No matter what Dallas does on the field, they can’t seem to figure out how to have a preemptive solution to any of their big players’ contracts. It’s a major problem.
They wait, and they wait, and they wait, and it almost always drives up the price and creates an unnecessary distraction for the entire organization.
Unfortunately, we are headed for a similar problem right now. They just can’t help themselves.
Dallas has decided once again to sit on their hands while one top player became one of the best and most expensive players in the league, and they are doing the same for a recent acquisition that has a chance to explode in 2025.
Let’s talk about both of these guys and why the Cowboys’ contract extension gambles might come back to bite them once again.
Micah Parsons: Another Homegrown Talent’s Price Tag Surge
It was clear from the jump that 2021 first-round pick Micah Parsons would be a star. He was an All-Pro in his rookie year and nearly won the DPOY award, yet, four years later, the Cowboys have not extended his contract.
It is hard to imagine any other franchise operating this way with Parsons. Dallas should have inked a new deal the first chance they had, given his career trajectory.
It is the same thing that happened with Prescott and Lamb; they just don’t learn from mistakes.
Parsons, 26, has now seen Myles Garrett receive a $40M per-year deal, and he is significantly younger than his Browns counterpart. If Parsons reaches that Garrett level this season with a DPOY win, there is no reason he wouldn’t break the $40M mark.
You could argue this is the worst moment yet in the Cowboys’ contract extension chronicles, as they will likely pay an insane amount for a non-quarterback that could have been extended years ago.
It’s a gamble in the biggest way. If Parsons excels, as he always does, get ready for a very tense negotiation heading into free agency.
George Pickens: Potential Could Kill Cowboys’ Chance At A Deal
Dallas traded a premier pick in the 2026 NFL Draft to acquire George Pickens from Pittsburgh. In doing so, they set themselves up for a breakout season from the young receiver and an unreachable price tag this winter.
There has been zero talk of an extension between the two sides. They made the deal happen, and now we are poised for an all-eyes-on-Pickens year.
In his career, Pickens has played on some flat-out poor offenses. He has still produced, don’t get me wrong, but he has never had the chance at production that he will have this season with Prescott.
There is a very real world where this kid becomes an All-Pro in his own right, and with Lamb on the books, you’d likely see him depart in free agency for a huge contract.
Would Pickens and his team, knowing this possibility, sign a deal before the year? It’s unlikely, but if Dallas had met him at a fair price, it could have happened.
It’s a rare example of the Cowboys trading for a star player at all, and I would hate to see it squandered by their hesitancy with extensions. This is a tough business; make the hard call, pay the big bucks, and push as hard as you can to get out of the mud the organization has been stuck in.
