3 contract decisions that will haunt the Dallas Cowboys

• Cowboys painted themselves in a corner with Dak, again

• Tyron Smith is too unreliable at this point

• Michael Gallup needed to prove his worth before the deal

Jan 16, 2023; Tampa, Florida, USA; Dallas Cowboys wide receiver Michael Gallup (13) reacts after
Jan 16, 2023; Tampa, Florida, USA; Dallas Cowboys wide receiver Michael Gallup (13) reacts after / Kim Klement-USA TODAY Sports
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Overall, the Dallas Cowboys front office has done a decent job of building their roster in recent years. They've avoided signing over-priced free agents and have done well in the NFL Draft.

That doesn't mean they're without fault — and we can see the way they've overpaid in-house players such as Ezekiel Elliott as an example.

While we won't be looking at that deal (since it's now in the past), here are three contract decisions that could come back to haunt the Cowboys.

3. Re-structuring rather than extending Dak Prescott

The Cowboys never learn when it comes to shooting themselves in the foot.

Right after seeing DeMarcus Lawrence's value increase when they played hardball, the Jones family decided to play hardball with Dak Prescott. They balked at a contract rumored to be $32 million per season in 2020 and instead, paid $31.4 million on the franchise tag.

They tagged him again in 2021 before finally signing him to a deal worth $40 million per season. That means they cost themselves $8 million per season by waiting to pay the man they knew was the franchise quarterback.

In 2023, they're again proving they haven't learned. Prescott enters the year with just two seasons left on his deal and Dallas turned to him for cap relief. But instead of working out an extension, they restructured his contract — and he will now count for $59 million in 2024.

Yes, they can extend him before next season and lower that cap hit but they will again have to pay a lot more. Right now, quarterbacks are signing for roughly $45 million per season but that will increase in a hurry — especially with Justin Herbert and the Chargers discussing a new deal.

This means Dallas is likely going to see Prescott command closer to $50 million — especially if he has a bounce-back year in 2023. They had some leverage entering the offseason but they ended up giving it all to him.