As Jerry Jones rambled on about his contractual strategy regarding his franchise quarterback at the start of Dallas Cowboys training camp last month, leaning into a banal analogy in which he compared himself to an option quarterback clinging to the ball until the last possible moment, one thing became abundantly clear to executives, contract negotiators and agents around the NFL.
The owner of America’s Team no longer understands how to read a defense.
To continue Jones’s hackneyed trope regarding his unwillingness to accept contractual truths about Dak Prescott’s value, he has held on to the ball too long as less-accomplished passers such as Trevor Lawrence and Tua Tagovailoa reset the market this offseason and has given himself no room to escape. Jones, in the estimation of a half-dozen NFL contract negotiators and evaluators, has left himself exposed, vulnerable and without leverage.
There are but two outcomes ahead after Jones capitulated on no franchise tag and a no-trade clause during Prescott’s previous arduous negotiation: Give the quarterback $60 million per season (or close to it) ASAP or lose him for a 2026 compensatory draft pick in March when some other billionaire makes Prescott the highest-paid player in NFL history.
Either is akin, at this point, to taking an embarrassing sack – maybe even a strip-sack.
“Jerry totally screwed this up,” said one NFL general manager who has dealt with numerous high-end quarterback negotiations. (He spoke on the condition of anonymity because he is not permitted to comment on other teams’ personnel moves.) “Either pay him or lose him.”
Certain things become unarguable, especially at quarterback. And when a 31-year-old quarterback of a team as high profile as this, who nearly reached the pinnacle of league compensation in 2021 even coming off a season marred by injury, enters camp willing to play out the final year of his deal for a modest $40 million (including incentives, but not including all his money from Nike, Gatorade, Sleep Number and so on), after a season in which he finished second in MVP voting and led the league in touchdown passes, that player is going to cash in. Massively. And with timing everything in the NFL – hence that moment when Joe Flacco became the highest-paid player in league history – and with the quarterback market exploding in the past few months (and even wide receivers now making $35 million per season), Prescott’s timing is nothing less than impeccable.
“It makes no sense whatsoever,” said a longtime NFL contract negotiator who is not permitted to speak about players under contract to other teams. “Jerry has cost himself a not-inconsequential amount of money already, and it keeps adding up pretty quickly with how the market has moved.
“I can’t tell you precisely when we reached the point when it became an irrefutable universal truth that at certain positions the next guy up was going to leapfrog everyone else, even if he wasn’t quite the same caliber of player, and reach a new price-point plateau. But in this instance it is absolutely irrefutable that this is going to be the case. As someone on the other side of these things, trust me, I wish it didn’t work this way. But it does. This is our reality.
“They’ve absolutely painted themselves in a corner as a franchise with the quarterback, and I’m honestly even more baffled they didn’t get ahead of this with [superstar wideout CeeDee Lamb, who is holding out]. That’s close to $100 million a season on those two players alone, no matter what Jerry thinks, and that’s us talking today. By March, we’re looking at even more.”
And multiple people I spoke with believe next offseason will offer one of the weakest quarterback free agent and trade markets in years. Almost all the quarterbacks on track to be available project as backups, while Kirk Cousins might be the most appealing option in a trade. That is another strong factor working in Prescott’s favor – and his representatives are well aware.
I asked an agent who has negotiated plenty of high-end quarterback deals how he would approach this situation. “Dak gets to the top of the mountain, and it’s not close,” he said on the condition of anonymity, not wanting to comment publicly on a player he does not represent. “I think Jerry has lost it.”
Once revered as a billionaire who would go all-in to build and retain championship rosters, Jones is now scoffed at when he mentions the Super Bowl. He has aged into more of a spendthrift, seeking bargains and living on the margins. Outside of his quarterback, who has the top QB rating in the NFL over the past three seasons, no other Cowboys player under contract is making even $20 million this season, while his franchise value soars and the revenue streams run deeper than ever.
Per Spotrac, the Cowboys are last in cash committed to payroll for 2024 – nearly $10 million behind anyone else. Jones was in the top three in spending during the pandemic (in 2020 and 2021), but team spending slipped to 29th in 2022 and was 11th in 2023.
Opinions vary on whether Jones will buck such trends for Prescott and Lamb. (Jones said Thursday there’s no “sense of urgency” to extend the receiver.) One longtime personnel executive, who has a pretty good bead on Jones after decades competing with him, believes he might understand the owner’s internal struggle. He’s more confounded by the 81-year-old not yet signing Lamb than he is by the Prescott situation because, even if Jones were to go in a different direction at quarterback in 2025, he would still need Lamb, just entering his prime, to be a vital offensive cog.
“I don’t think he sees himself winning the Super Bowl with this quarterback,” the executive said on the condition of anonymity, limited from commenting on other rosters by NFL contract language. “And, honestly, when I look at his roster, I agree with him. I wouldn’t want to pay [Prescott] $60 million, either. But at [Jones’s] age, what else is he going to do? Start over with a rookie next year? He doesn’t have three years to play that out.
“Jerry’s frustration with not being able to get his team over the top is showing more and more, and he knows time is not on his side. However much he used to listen to other people about the management of his team, I think that’s happening less and less now.”
With the owner also the head of all things football – the Cowboys’ front-office structure is among the most convoluted in professional sports – this family-run business appears to be spiraling further and further away from another Lombardi Trophy. (Its most recent was in the 1995 season.) Nine months from now, someone else will be waiting with an open checkbook for Prescott – after striking out with Derek Carr and Jimmy Garoppolo, keep an eye on Mark Davis of the Las Vegas Raiders. But if the Cowboys were somehow a normal franchise, with the owner not so intimately involved in every nuance of the deal, what advice would the accomplished contract negotiator offer? What would he tell Jones?
“It’s pretty simple,” the executive said. “If this player is a free agent and he has a market – and if you have two teams, you have a market, and Dak Prescott will have a market – then he will get $60 million a year. I don’t understand why we haven’t done this already or why we aren’t doing this now. The price is the price.”