Dak Prescott beat Jerry Jones at his own game – again – and that doesn't bode well for Cowboys

Dak Prescott’s detractors will typically point to his lack of signature wins in the NFL. If only they handed out rings for taking your boss to the woodshed.

On Sunday morning,–again– for the second time in little more than three years, the Dallas Cowboys’ veteran quarterback – after protracted negotiations – extracted a top-of-market contract extension from team owner Jerry Jones. Prescott became the NFL’s first $60 million-per-year man (over four seasons), a significant jump from his closest peers, while pulling down a record $231 million in guarantees … and proving anew that he’s among the finest businessmen – think Kirk Cousins, Darrelle Revis, Drew Brees, Walter Jones or Deion Sanders – to ever wear a professional football uniform.

And while Prescott’s agent, Todd France, deserves ample credit, too, the three-time Pro Bowler handed essentially all of the leverage to his representation, entering the walk year of his expiring four-year, $160 million pact after being the league's MVP runner-up and posting an NFL-best 36 TD passes in 2023. Prescott, a four-time NFC East champion, also couldn’t be traded or tagged at a time when the apex of the quarterback market was paying $55 million annually.

Count perennial All-Pro linebacker Bobby Wagner of the Washington Commanders – he’s served as his his own agent for eight years – among the impressed.

"I think you have to want to do the work and learn. You have to be willing to take risks,” Wagner told USA TODAY Sports, referring to the franchise tag Prescott played on in 2020, when his season was aborted after five games due to a compound fracture to his leg and a dislocated ankle.

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“You have to know your market. If you have those things, then you put yourself into a good position."

Prescott certainly did, expressing no outward frustration this summer as Jerry Jones dragged his feet and made various comments that left room for interpretation but evidently didn’t bother his biggest star. Prescott himself casually noted how many superstars at his position eventually concluded their careers with different clubs – an outcome he seemed headed for as talks languished.

“I understand the business point blank,” Prescott said Sunday. “The game is a business.”

And legendary entrepreneur Jones cracked at his own game before the Cowboys faced the Browns in Cleveland on Sunday afternoon, opting to shell out his second premium compact in two weeks after making All-Pro CeeDee Lamb the second-best compensated wide receiver (four years, $136 million) in the league behind Justin Jefferson.

"The NFL, you're not gonna play in it forever,” San Francisco 49ers tight end George Kittle told USA TODAY Sports. “I'm happy for guys that make the money they deserve to make. And when you win a lot of football games – when you're winning all the time – I think you deserve to get paid money.

“Dak's always had the Cowboys in the playoffs, playing at a high level.”

So, yes, Prescott – knowing when to apply pressure behind the scenes and when to let matters play out around him – won another major fiscal battle three years after his previous arrangement paid better than anyone not named Patrick Mahomes. Yet therein lies an important distinction – and one that may mean Jones will continue to lose the football wars nearly three decades after Dallas last appeared in the Super Bowl or even an NFC title game.

Prescott – and you can hardly blame him – has consistently maximized his value, similar to Cousins and even Cleveland’s Deshaun Watson, both proponents of the fully guaranteed contract.

"I don’t play for the money. I think when you focus and you control what you can control things like that just happen,” Prescott said after Sunday’s 33-17 drubbing of the Browns.

“I don’t care to talk about money. That was the only annoyance in this ordeal is having to answer questions over and over and time and time again about the negotiations. I just wanted that behind me. If it meant me not being here, which I did not want to think about, I said that over and over again. I just wanted to be at peace with whatever the decision was.”

Yet this decision will have ramifications – in fact, it already has. And Prescott will doubtless face more questions about cash flow in the future. Players like Mahomes and Tom Brady, who are increasingly paired exclusively in the NFL’s “GOAT” debate, were certainly handsomely paid – but both signed deals that afforded the Kansas City Chiefs and New England Patriots, respectively, the financial flexibility to upgrade what became and remained championship rosters.

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Like Cousins, Prescott and Lamb have opted for shorter contracts that get them back to the negotiating table more quickly – though that often hinders their teams from making major free agent acquisitions elsewhere. (And we’ve seen the results in the playoffs for Cousins and the Cowboys, unsuccessful trips to the divisional round their high-water marks this century.) That approach may be especially problematic in Dallas, where Jones often finds himself behind the curve when it comes to doling out new deals and could be in a similar situation next year, when pass rusher extraordinaire Micah Parsons must be given the raise he’s already earned.

As for the here and now? The inability to get Prescott and Lamb paid earlier – and they certainly had a role in that – crippled the ability of the Cowboys, NFC East champions two of the past three years and winners of 12 regular-season games in all of those campaigns, to improve or even maintain their roster this offseason. And this is a team that has routinely fallen short in the postseason under head coach Mike McCarthy, including a 48-32 loss to the Green Bay Packers in the wild-card round in January, an outcome that wasn’t even as close as a fairly wide margin indicates.

"This is the worst offseason I can remember for Jerry as the GM. Like, do we honestly think they got better this offseason? I mean, what did they do?” former NFL quarterback Alex Smith, now an ESPN analyst, said Sunday.

“I know they got these contracts done, but they got (run) out of their own building in the first round of the playoffs and did nothing this offseason – nothing to improve. … I don't see it. I know they've won 12 games the last three years. I don't see them hitting that this year."

The Cowboys looked like world-beaters Sunday, albeit against a crippled Cleveland team missing several key starters and against a quarterback, Watson, who has become emblematic of the inherent risk of fully (or heavily) guaranteed pacts after signing his widely scrutinized package. But Jones will be heavily reliant on a ballooning salary cap given how much of it Prescott, Lamb and Parsons will surely eat up in future seasons while aiming for quick turnaround times at a second or third dessert. And don’t forget, Dallas will also have to pay or replace G Zack Martin, DE DeMarcus Lawrence and WR Brandin Cooks, among others, after this season.

“I’ve seen too many very important deals not work out just because of miscalculating the right time, when everyone’s ready to go,” Jones said Sunday.

“My prayer is that we have the ability to put the supporting cast around (Prescott).”

Prayers can pay off. But when it comes to football, history suggest a better plan would be preferable in Dallas.

Follow USA TODAY Sports' Nate Davis on X, formerly Twitter, @ByNateDavis.