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Dak Prescott holds the cards in contract talks with Cowboys

Mike Florio and Chris Simms analyze how the Cowboys have restructured deals for the cap to this point and question who Dallas would choose if they found themselves in a financial bind.

Dak Prescott had the Cowboys over a barrel in early 2021. He had them firmly so far over a barrel that year that he was able to do a new deal that already put them over a barrel again in 2023.

The Cowboys need to fix his contract now, in order to avoid a potential salary-cap disaster in 2024.

Under Prescott’s current deal, given its original structure and past restructurings, Prescott will have a cap number of $59.455 million in 2024. This year, it’s only $26.8 million. So the Cowboys need to re-do the deal far more badly than Prescott does.

Prescott’s other source of leverage comes from the fact that the Cowboys, as a practical matter, won’t be able to tag him in 2025. Thus, absent a new deal in the next two seasons, Prescott becomes an unrestricted free agent.

The entire problem traces to the team’s decision not to get Prescott signed to a reasonably robust deal after 2018, his third season. Instead, the Cowboys took full advantage of the bargain-basement fourth year of his rookie deal, applied the franchise tag in 2020, and then finally signed him to a four-year, $160 million deal in March of 2021.

The deal was structured to get Dak back to the table sooner than later. The Cowboys need to rush back to the table now, to avoid the double whammy of a cap charge of nearly $60 million next year and Prescott walking away.

The challenge becomes figuring out the next deal. Prescott’s last deal, worth $40 million per year, shows that he cares very little about being able to crow that he has the highest new-money APY in league history. He values cash in hand, along with the flexibility to get more cash via his next contract. In both respects, his contract from 2021 counts as the best one any quarterback has done, perhaps with the lone exception being the Deshaun Watson aberration.

For the Cowboys, the question becomes whether, at some point, they should just start over. Draft a new quarterback. Find a veteran starter. Do whatever they have to do to stop the funhouse ride that has become zero fun, sir for the team.

Dak is currently not one of the short-list franchise quarterbacks. He’s just not. He’s never led his team to an NFC Championship. He seems to have slipped a bit in 2022.

That makes now a great time to extend the deal. Prescott might not expect to become the highest-paid player in football. If he re-establishes himself as a top-five guy in 2023, he will.

Regardless, the Cowboys need to stop the doomsday clock that is currently ticking toward a $60 million cap number in 2024. Dak knows it. And it gives him all the leverage he needs to get a deal that likely will cause many to think he’s grossly overpaid in comparison to other high-end quarterbacks.