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Todd Archer, ESPN Staff Writer
FRISCO, Texas — As we wait and wonder when or if the Dallas Cowboys and Dak Prescott will come to an agreement on an extension in 2024, let’s play out what some would call the worst-case scenario: The quarterback doesn’t sign an extension between now and January and is set to become an unrestricted free agent in 2025.
But first, here are a couple of ways they could get to that point:
The Cowboys make the playoffs for the fourth straight year, hoping to get to a Super Bowl for the first time since 1995.
In order to get there, Prescott will have had another top season, like he did in 2023 when he led the NFL in touchdown passes with 36 and threw for 4,516 yards. Given the current state of the roster, it will likely be Prescott’s finest season because the Cowboys have to replace starting left tackle Tyron Smith, center Tyler Biadasz, tailback Tony Pollard and wide receiver Michael Gallup.
Or …
The Cowboys miss the playoffs, but Prescott has what has become his average season: 25 touchdown passes and nine interceptions. He plays well enough to warrant a new deal, but there are too many holes on the roster to get back to the postseason.
What happens next?
It will become a mad dash from the end of the regular season to March 12, the start of the 2025 league year, for the Cowboys to sign Prescott to a new contract.
Through all of this, that is the deadline of deadlines.
Without a new contract by then, Prescott will count at least $40.46 million against the 2025 salary cap, and he will not be on the Cowboys’ roster.
With a contract done before then, Prescott’s cap number will be at least $25 million as a result of the restructures the Cowboys have used on the current deal, including converting his $5 million roster bonus earlier this month. Add in the yearly proration of a new signing bonus plus his base salary, and it’s likely Prescott’s cap number on an extension will exceed $40 million in 2025.
In January, we presented three options the Cowboys had with Prescott’s contract in 2024: do nothing, add voidable years to his deal or sign him to a massive contract extension.
Turns out, they have done a little of the second option so far and not so much of the third. They added voidable years to his contract, through 2028, after converting his roster bonus, but ultimately have done nothing else.
They could still restructure his deal by converting his $29 million base salary into a bonus and open up $18 million or so in cap room. They haven’t done that yet, and with big-money free agency over, it might make more sense to just keep the contract as is. If they do restructure the base salary, then Prescott would count close to $58 million against the 2025 cap if he doesn’t have an extension before the start of the next league year.
After recently converting his roster bonus, Prescott counts $55.45 million against the 2024 salary cap instead of $59.45 million.
Based on everything owner Jerry Jones and executive vice president Stephen Jones have said this offseason, the Cowboys were not going to be players in free agency even if they had compelling salary cap room to make additions. It’s not what they want to do, although this year’s free agency plan has been even slower than in recent years, with the Cowboys adding only linebacker Eric Kendricks at this point.
Prescott has the leverage with a no-trade clause and the team’s inability to use the franchise tag on him in 2025.
The Cowboys can hope for a team-friendly deal, but they were hoping to get one done in 2019, 2020 and 2021 and never did. Prescott and his agent, Todd France, played the negotiations perfectly with the quarterback maximizing his 2021 deal (four years, $160 million) while being able to call the shots again when it expires after the 2024 season.
The Cowboys are taking a gamble if they are unable to get a contract extension done with Prescott by the start of the 2025 league year.
How many available quarterbacks are going to be better than Prescott? Likely none.
But if Prescott does not get them to the Super Bowl after nine years as their starting quarterback, it would be fair for the Cowboys to ask if he will ever do it for them.
And how many teams will be in the market for a quarterback in 2025, especially given the teams that will select a quarterback early in the upcoming draft?
Almost all of these teams have contingencies on what happens in 2024: Pittsburgh Steelers (if Russell Wilson and/or Justin Fields don’t work out), Tennessee Titans (if Will Levis doesn’t work out), Las Vegas Raiders, New Orleans Saints, Seattle Seahawks, Los Angeles Rams (if Matthew Stafford retires), Minnesota Vikings, New York Giants (if they don’t draft a QB in the first round) and Denver Broncos (see the Giants).
How many of them will be able to meet Prescott’s contractual demands? Certainly not all of them. How many of them would be a preferred destination for Prescott? Certainly not all of them.
If Prescott gets the Cowboys to a Super Bowl, then the Joneses will gladly pay him whatever he wants.
It’s a game of risk. And for the next 11 months we get to see it all play out.