Cowboys, Jerry Jones Have No Wiggle Room On Dak Prescott’s Contract

Prescott is set to become a free agent after this season, putting himself in an excellent bargaining position with Dallas.

Dallas Cowboys quarterback Dak Prescott reacts during the first half against the Green Bay Packers for the 2024 NFC wild card game. / Tim Heitman-USA TODAY Sports

As one of my sons is living there, I have been spending a lot of time in Dallas these days, and I’ve noticed a lot of winning going on with their pro sports teams. Major League Baseball’s Rangers are fresh off a World Series championship and, as of this writing, the NBA’s Mavericks and the NHL’s Stars are deep in the playoffs in their conference finals. Noticeably absent from this discussion are the Cowboys, considered the most valuable sports franchise in the country, if not the entire world. As Dallas revels in this winning boon, the Cowboys franchise is certainly not a part of it.

When we last left the Cowboys on the field, it was on an icy January afternoon in Dallas where my sons and I (still Packers fans from our many years there) watched the underdog Packers’ demolition of the Cowboys, where it seemed the nearest defenders to Green Bay’s receivers were in Plano. Many, including this writer, thought that performance would cause mercurial Cowboys’ owner Jerry Jones to make some dramatic moves, starting with the firing of the head coach and continuing with some major subtraction and additions.

But, well, no. Jones did not fire McCarthy. The Cowboys have not yet secured contract extensions with their young stars on each side of the ball, CeeDee Lamb and Micah Parsons. And their most high-profile acquisition has been the return of Ezekiel Elliot, now a diminished version of what he was in his prime with the team. Hanging over all of this, and perhaps causing all of Jones’s inaction and reticence, is the contract situation with their quarterback.  While Dak Prescott is “only” making $29 million in salary this year, his $55.4 million cap number is an albatross hanging over the team.

Business of football champion

I have long remarked about the best contract for a young quarterback in recent years—beyond the now aberrational deal for Deshaun Watson—was the Prescott contract.

While media and fans were attracted to the shiny numbers of Patrick Mahomes’s 12-year contract or Josh Allen’s eight-year contract or the recent seven-year contracts for Joe Burrow and Justin Herbert, those contracts are all wins for the teams simply due to their extended length. Those players may never leverage the constantly-escalating marketplace for top quarterback contracts. Those extraordinarily long deals will cost tens (if not hundreds) of millions of dollars, and their career earnings will not compare favorably to those of Prescott.

While teams were lured by long deals, Prescott and his agents chose a more lucrative path. Not only did they secure a top-of-market for the time (2021) salary of $40 million per year, they negotiated something even more valuable: a short term of four years.  And they did so coming off a one-year franchise tag deal and a gruesome foot injury (debunking the erroneous narrative that star players lose market value if injured in a contract year).   

Prescott’s four-year deal, combined with the inevitable cap restructures that the Cowboys negotiated since (the Cowboys always need cap restructures from their highest paid players) gave him extraordinary leverage. It meant that he would cause such cap pain to the Cowboys in the latter years of the deal—now—that the team will have to either: 

1. Hamstring their team-building this year by carrying the Prescott contract as is.
2. Negotiate a new contract, with Prescott holding the upper hand.
3. Plan towards a cap-killing franchise tag number next year.
4. Plan towards allowing Prescott to enter the hallowed ground of NFL free agency in 2025.

But here is the kicker: whether from the Cowboys or another team, Prescott’s next deal will go from his current $40 million per year to to $55 million per year or above.  What Prescott and his agents did with his contract situation was very strategic.

Contracts not about “how good,” more about timing

The Prescott situation illustrates a point that many outside the business of the NFL never fully understand: contract negotiations are not about “how good” a player is. Rather, the key elements of a negotiation are timing and marketplace.

Contract negotiators, whether from the team side or the agent side, are not (or should not be) scouts, nor are they sports talk media personalities. Serious negotiators don’t waste time on debates regarding, for example, whether Prescott is “better” than Mahomes or Allen or Burrow or Herbert or Hurts, etc.  That ship has sailed; those players are locked into contracts that far exceed the length of Prescott.  

Prescott’s negotiations, rather, are about the fact the Cowboys only have one more year of contract control. The current situation without a renegotiation is, in itself, cap-prohibitive. A franchise tag number next year would also be cap-prohibitive, and the marketplace for top-level quarterbacks has exploded. 

Simply, Prescott has the Cowboys over a barrel. And it is not a stretch to say this: the lack of an extension to Prescott’s contract has put everything on the table with the future of the franchise.

Jones and Prescott before a game against the San Francisco 49ers at Levi's Stadium. / Kyle Terada-USA TODAY Sports

A new Jerry Jones?

The Jerry Jones that most people know is someone full of gusto and bravado who is prone to react emotionally. In this case, that would mean he would pay Prescott top dollar, with a huge bonus for cap proration that would help him spend hundreds of millions more to sign Parsons and Lamb. It is what the Cowboys have traditionally done, rewarding their stars with oversized contracts, loading them up with up-front cash to get them under contract.

However, as we now enter the summer, I am not so sure we have that same Jones.  

As noted above, he did not fire McCarthy, letting him coach out the final year of his contract.  He has not extended Lamb or Parsons.  The team underachieved in the most important games in recent years. What if we are at an inflection point with this Cowboys team as currently built, and a reckoning for the way the Joneses have always done business as team owners?

Consider: what if Jones and the Cowboys decide to roll the dice with Prescott this year? What if they put off any negotiations, knowing the price tag will only rise, and leave the quarterback position uncertain after this season?  History says it will not happen, but maybe this year—and this Jones—will be different.

Listen, the odds are that Prescott, Lamb and Parsons will all be extended, with over $100 million of signing bonus money funneled to them to create short-term cap relief yet onerous long-term cap and cash obligations.  

But maybe, just maybe, the once-impulsive and knee-jerk Jones has become more pragmatic, more willing to wait and see, more comfortable in being uncomfortable with the future. It could happen.

Either way, however, Prescott will continue to win, and win big, in the business of football.