Prescott is entering the final year of a four-year contract signed instead of playing under the second franchise tag. He won his second championship after the Cowboys refused to extend his rookie contract after three years and then completed his four-year rookie contract and received the franchise tag for the first time.

This gave him a significant advantage in early 2021. He did what team owner Jerry Jones had done his entire life when he had significant power.

He took full advantage of it.

And so, on the first day of the 2024 league year, Prescott's cap number will jump from $ 26.832 million in 2023 to $ 59.455 million. The Cowboys have no choice but to extend his contract before then to reduce the massive cap hit.

This again gives Prescott a considerable advantage. What would he do?

And what would Jerry do?

Prescott will undoubtedly come out of the negotiations with another market-level deal. He can essentially set his price. The situation stems directly from Jones' stubbornness and frugality after the 2018 and 2019 seasons.

When the Cowboys chose to block Dak from playing under the franchise tag for a second year in early 2021 and then Kirk Cousins became an unrestricted free agent in early 2022, the Cowboys signed Dak to a four-year, $160 million contract that ideally would have forced them to sign him to another deal after 2022 (although the Cowboys would have liked that, it didn't happen) and before the $59.4 million cap hit begins on March 13 at the latest.

The Cowboys can't trade him. While he will only (only?) earn $34 million in 2024, a trade before June 1 would trigger a $61.9 million cap hit. Cutting him before June 1 would result in the same dead money figure for 2024.

Beyond the benefit of the $59.4 million cap figure set for 2024, given the structure and terms of the deal, the Cowboys will not be able to tag him in 2025. (Even if they could, the cap figure would be 144 percent of his 2024 cap figure - $85.5 million - since the Cowboys applied a second franchise tag before signing his extension). Thus, he will be an unrestricted free agent next March without an extension.

And even if they decide to deal with the $59.4 million cap figure and allow him to become a free agent in March 2025, they will still have to deal with $36.46 million in dead money from the contract next year. That's more than the $35 million Tom Brady left the Buccaneers this year.

So basically the Cowboys are screwed. Dak knows that. He knew it three years ago and he did what Jerry would do. Why shouldn't Dak do the same thing Jerry would do this year?

Fortunately for the Cowboys, Dak has played well enough to justify a big contract in 2023. It would look very strange if, for example, they gave him a deal worth 55 million dollars a year if he scored 23 touchdowns and threw 15 interceptions like he did in 2022.

But it would have been understandable. The Cowboys made a mess after his third and fourth year. Instead of letting Dak play under the $37 million tag in 2021 and become a free agent in March 2022, they backed themselves into a corner. As the final year of this deal approaches, they are getting more and more tightly locked in.