Mike Florio raises concerns about Cowboys ahead of Dak Prescott’s new contract decision - “At what point are they going to start over?"

As the 2023 season approaches, the Dallas Cowboys are already making plans for the future, including the 2024 season. It's no secret that quarterback Dak Prescott is entering a crucial year in his contract. The $160 million extension he signed in 2021 has had a significant impact on the team's roster construction.

Most notably, the Cowboys had to release rushing leader Ezekiel Elliott. His supposed successor, Tony Pollard, is on the franchise tag and may be removed after the season for rookie Deuce Vaughn.

And according to NFL analyst Mike Florio, the team's executives has only themselves to blame for this situation, Speaking on Pro Football Talk, he said:

"Don't blame it on Dak, blame it on yourself for screwing around and putting Dak in a position of extreme power… He's got mechanisms built into this contract that if they don't get it done, he becomes a free agent. They can't tag him the way the voids work and when they kick in it's been perfectly and expertly negotiated to set him up for another huge payday or a trip to the open market.

He also insinuated that they would now have to figure a way to reduce payroll while keeping Prescott happy:

And the sooner they do it the better off they're going to be but don't blame it on him; blame it on yourself. It's not his fault, it's your fault for mishandling the situation. He's gotten paid and now what they need him to do is a contract that reduces his cap number. That's on them to figure it out and it's going to be interesting this time around because at what point are they going to start over?"

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How crucial will the 2023 season really be for Dak Prescott's contract negotiations?

Mike Florio is not the only analyst who believes 2023 will be a crucial year for Dak Prescott's contract situation. Speaking on ESPN's Get Up!, insider Dan Graziano predicted that the Cowboys might make their quarterback prove himself before he could secure another extension:

"Prescott's contract expires after 2024. His cap number this year is a manageable $26.8 million, but next year it balloons to $59.5 million. If the Cowboys don't extend Prescott beyond 2024, they are effectively committing to carrying that cap number and making Prescott prove he deserves a new deal.

"Given their lack of postseason success with Dak as their QB, this path likely makes the most sense."

That being said, he still believes that the Cowboys will look to structure any extension in such a way that Prescott does not adversely affect their cap situation:

"It would be very surprising if they didn't do an extension this offseason that knocked down that 2024 cap number and made it clear to the world that Prescott's future in Dallas is not in question."