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 re-sign 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.

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.

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 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.