Jerry Jones' worst NFL enemy remains Jerry Jones

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Jerry Jones, owner of the Dallas Cowboys, has an NFL nemesis hell bent on keeping him from reclaiming the glory of the 1990s. That man is Jerry Jones, de facto general manager of the Dallas Cowboys.
To be clear, Jones' talent evaluation and trust in his scouts remain top notch. The Cowboys continue to generate elite homegrown talent on a semi-regular basis. Draft-n-Play Jerry Jones? That guy is an asset. But once those guys get near the end of those rookie contracts, Contract Extension Jerry Jones comes out. And while Contract Extension Jerry is great for his stars' checking accounts, it's actively hindering the roster around them.
None of that is new. Jones' propensity to drag his feet early in negotiations has often led to more expensive deals down the line for players Dallas cannot afford to see leave. What could have been a five year, $262.5 million extension for Dak Prescott in 2023 (using Justin Herbert's deal as a comparison) eventually became a four year, $240 million deal in 2024, paying him $5 million more annually than any other NFL player ($231 million of that is guaranteed). CeeDee Lamb was always set to reset the wide receiver market. Doing so at the eve of the 2024 season lined him up for $34 million per year instead of around $30 million had he signed the offseason prior ($100 million of that is guaranteed).
That creates salary cap bottlenecks down the line for a team that's perpetually high on star power and often low on depth. Jones' hesitation has logic behind it; he's waiting to see if a young player's production wanes before making a massive commitment. At the same time, that keeps said young player on a less expensive salary, which allows some breathing room to pay off the other massive extensions looming around the corner.
However, that strategy keeps costing him money while antagonizing the players on which he relies. And Monday's comments about Micah Parsons, whose upcoming extension gets pricier each month? Fairly antagonistic!
"Even if" is a bold way to address your team's desire to keep a 26-year-old with 52.5 sacks and four Pro Bowl honors in four seasons as a pro. Yet, here is Jones, quietly negging a player who has only missed four games due to injury in his career to date (a fifth game, in Week 18 vs. the Eagles in 2021, was due to COVID-19). Jones also added 'I am not the least concerned about having any dangling participles out here on a contract,' which is a folksy, homespun way of suggesting that, yep, this approach will once again cost Dallas extra money as a luxury tax for an owner/manager who lives for the escalation of contract negotiations but still seems to lose the big ones more often than he wins.
Parsons, by the way, took notice. How could he not?
So why is Jones waiting? He offered a couple rationalizations. The first, naturally, was the fleeting nature of mortality and rising tide of reckless drivers.
The second, more sensible option was that he'd been burned before and had some regrets. And Jerry Jones, because he is Jerry Jones and you do not have to speak diplomatically when you own a superyacht, named names beyond Prescott and his nine missed games in 2024.
Trevon Diggs was an All-Pro his second season in the league and a Pro Bowler the third. He signed a five year, $97 million contract to become one of the league's five highest paid cornerbacks, then missed 15 games due to injury in 2023 and six games in 2024 while providing good-not-great coverage. Steele signed a five-year, $82.5 million contract in 2023 after ascending to a starting role at right tackle, which made him the ninth-highest paid offensive tackle in the NFL. He hasn't missed a game since then, but his play hasn't lived up to the salary even though he'll only be the league's 25th-highest paid tackle in 2025.
Jones paid market value for a boom-or-bust cornerback and a rising young tackle. One of them was derailed by injury and the other has struggled, but there's room for both players to revert to form (Steele is the oldest of the two and only 28 years old). Jones isn't in the hope business, however, he's looking for results. And these results align more closely with his wait-and-see philosophy than the fact Lamb was an All-Pro for the third straight season last fall.
Thus, the Cowboys will likely be stuck with the privilege of paying Parsons a record-setting amount in the late stages of the 2025 preseason. A deal to beat out the $41 million in annual salary to TJ Watt -- resetting the market last offseason probably would have clocked in closer to $36 million per year -- could leave the franchise committed to something like $137 million in annual average salary to three players. That's not unmanageable, but it's a problem. Dallas has been so strapped for cap space in recent years that its top free agent additions the last few seasons have been:
2025: EDGE Dante Fowler Jr. (one year, $6 million)
2024: LB Eric Kendricks (one year, $3 million)
2023: RB Ronald Jones Jr. (one year, $1.25 million)
All the while, players like Connor McGovern, Dalton Schultz, Dorance Armstrong, Tyler Biadasz, Jourdan Lewis and Demarcus Lawrence left for cash elsewhere. That's not why the Cowboys have one playoff win since 2019, but it certainly doesn't help.
Monday's comments were a refreshing display of honesty. Not about Micah Parsons, of course, but about how Jones views his roster management. The sunk cost of paying a player who might get injured or fall off far outweighs the opportunity savings of paying young, proven players what they're worth before it gets damagingly expensive. Jones is content to lose leverage and give up more in guarantees than he would have years earlier if he can find data that rewards his wait-and-see approach.
That's not anything we didn't already know, but it's something else to hear Jones go out and effectively admit it. It's an approach that keeps the Cowboys from turning its stars into a constellation. And while it means guys like Prescott, Lamb and, eventually, Parsons all get truly lucrative contracts down the line, it also means they won't have the support to maximize the talent for which Jones is paying so much.
This article originally appeared on For The Win: Jerry Jones' worst NFL enemy remains Jerry Jones