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Dak Prescott’s critics usually point to his lack of wins in the NFL. If only they gave out rings for taking down your boss.
On Sunday morning, after lengthy negotiations, the veteran Dallas Cowboys quarterback secured a top-dollar contract extension from team owner Jerry Jones for the second time in just over three years. Prescott became the first NFL player to earn $60 million a year (over four seasons), a significant leap forward from his closest peers, while also collecting a record $231 million in guarantees… and proving once again that he is one of the best businessmen – think Kirk Cousins, Darrelle Revis, Drew Brees, Walter Jones or Deion Sanders – to ever wear a professional football jersey.
And while Prescott’s agent, Todd France, deserves a lot of credit, the three-time Pro Bowler ceded virtually all the power to his agent, entering the final year of his expiring four-year, $160 million contract after finishing second in league MVP voting and setting an NFL record with 36 touchdown passes in 2023. Prescott, a four-time NFC East champion, also couldn’t be traded or signed at a time when the top of the quarterback market was paying $55 million per year.
Among those impressed is longtime All-Pro linebacker Bobby Wagner of the Washington Commanders – he was his own agent for eight years.
“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 under in 2020 when his season was cut short after five games due to an open leg fracture and a sprained ankle.
“You have to know your market. If you have these things, you’re in a good position.”
Prescott certainly did, and he didn’t let it show this summer when Jerry Jones hesitated and made various comments that left room for interpretation but clearly didn’t bother his biggest star. Prescott himself casually noted how many superstars at his position ended up finishing their careers with other clubs – an outcome he seemed to be heading toward when talks stalled.
“I completely understand the business,” Prescott said Sunday. “The game is a business.”
And legendary entrepreneur Jones did his own thing before the Cowboys’ game against the Browns on Sunday afternoon in Cleveland, opting to shell out his second premium contract in two weeks after making All-Pro CeeDee Lamb the second-highest-paid wide receiver (four years, $136 million) in the league behind Justin Jefferson.
“You’re not going to play in the NFL forever,” San Francisco 49ers tight end George Kittle told USA TODAY Sports. “I’m happy for the guys that are making the money they’re making. And if you win a lot of football games – if you win consistently – then I think you’ve made money.”
“Dak always took the Cowboys to the playoffs and played at a high level.”
So, yes, Prescott — who knew when to apply pressure behind the scenes and when to let things go around him — won another major financial battle three years after his previous contract paid more than anyone not named Patrick Mahomes. But therein lies an important difference — and one that could 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, much like Cousins and even Cleveland’s Deshaun Watson, both of whom are proponents of the fully guaranteed contract.
“I don’t play for the money. I think if you focus and control what you can control, these things just happen,” Prescott said after the Browns’ 33-17 loss on Sunday.
“I don’t like talking about money. The only annoying thing about this ordeal was having to answer questions about the negotiations over and over again. I just wanted it over and over again. If it meant I wasn’t going to be here, which I didn’t want to think about, then I said that over and over again. I just wanted to be at peace with the decision, whatever it was.”
But this decision will have consequences—in fact, it already has. And Prescott will undoubtedly face even more questions about cash flow in the future. Players like Mahomes and Tom Brady, who are increasingly featured as a team in the NFL’s “GOAT” debate, were certainly paid handsomely—but both signed deals that gave the Kansas City Chiefs and New England Patriots, respectively, the financial flexibility to improve their teams, which became and remained championship contenders.
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Like Cousins, Prescott and Lamb have opted for shorter contracts that get them back to the negotiating table more quickly — even though that often prevents their teams from signing bigger free-agent deals elsewhere. (And we’ve seen the results in the playoffs for Cousins and the Cowboys; unsuccessful trips to the divisional round were their high points this century.) That approach could be especially problematic in Dallas, where Jones is often behind on new contracts and could be in a similar situation next year when exceptional pass rusher Micah Parsons needs to get the raise he’s already earned.
And what about the here and now? The inability to pay Prescott and Lamb sooner — and they certainly had a role in that — has hurt the ability of the Cowboys, NFC East champions in two of the last three years and winners of 12 regular-season games in all of those seasons, to improve or even maintain their roster this offseason. And this is a team that has consistently failed 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, a result that wasn’t even as close as a fairly wide margin would suggest.
“This is the worst offseason I can remember as Jerry’s GM. Do we really 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 made those contracts, but they got evicted from their own building in the first round of the playoffs and they didn’t do anything in the offseason – nothing to improve. … I don’t see that happening. I know they’ve won 12 games the last three years. I don’t think they can do that this year.”
The Cowboys looked like world-class players on Sunday, albeit against a weakened Cleveland team missing several key starters and a quarterback named Watson who became emblematic of the inherent risk of fully (or heavily) guaranteed contracts after signing his much-scrutinized package. But Jones will rely heavily on a rising salary cap, considering how much of it Prescott, Lamb and Parsons will surely eat up in future seasons while aiming for quick turnaround times on a second or third dessert. And don’t forget that Dallas will also have to pay or replace G Zack Martin, DE DeMarcus Lawrence and WR Brandin Cooks, among others, after this season.
“I have seen too many very important deals fail simply because of misjudging the right time when everyone was ready to go,” Jones said on Sunday.
“I’m praying we can put the supporting cast around (Prescott).”
Prayers can pay off. But when it comes to football, history suggests that a better plan would be desirable in Dallas.
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Follow USA TODAY Sports’ Nate Davis on X, formerly Twitter, @ByNateDavis.
