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.
Browns agree to terms with Myles Garrett on four-year extension with $40M per year average, including $123M guaranteed. (via @rapsheet, @tompelissero) pic.twitter.com/0is9ZDGKbo
— NFL (@NFL) March 9, 2025
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.
Dak Prescott, George Pickens, CeeDee Lamb pic.twitter.com/ZHOnwmUkqI
— Jon Machota (@jonmachota) May 20, 2025
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.
a Dallas Cowboys fan, since the 70’s I want to see how much money and guaranteed money Jerry Jones is going to pay both Micah Parsons and George Pickens
George Pickens said he didn’t want a contract extension from the Cowboys this year!! He said he wants to play the season for us first!! But if he does leave in free agency then we’ll just get our 3rd round pick back!! It won’t be until the 2027 draft, but we’ll still get get it!! And it mite even be better to get it in 2027 cause we’ll more than likely have 2 3rd round picks in that draft!! But that only depends on how good Pickens is for us!! If he shows he can be a top receiver in the NFL then he’ll leave in free agency and get a top dollar contract and then we’ll get our 3rd round pick back!! But if he just shows he can be a good WR2, then his price tag won’t be so high and we’ll have a chance to sign him to an extension!! And if he don’t take our offer and he leaves in free agency anyways, then chances are there will be a team out there desperate enough to sign him to a big contract and chances are we’ll still get that 3rd round pick or at the very least a 4th round pick in return!! Either way, we’ll get our money’s worth out of him!! But if I had to guess, after the way he’s played with those bad offenses, I think he’s gonna ball out for us and his price tag will be too high for us and he’ll leave in free agency for a top of the market contract and we’ll get our 3rd round pick back!! That’s just what I think will happen!!