Cowboys learning from massive mistake with Dak Prescott contract

The last time Dak Prescott and the Dallas Cowboys agreed on a contract extension to keep the franchise quarterback with the team that drafted him, it took several years. The process was drawn out. In the end, Prescott got paid and the Cowboys kept their signal-caller, but it was far from a straightforward ordeal.

This time around, dragging things out like they did the last time with Prescott, it would be extremely costly for both the Cowboys and Prescott's career CV. Prescott carries a $60 million cap hit for the Cowboys this year if his contract is not restructured. That would be obviously expensive, but moreover, it would prevent the Cowboys from making other important moves to keep Dallas competitive.

The salary cap is $240 million in 2024. Prescott's current cap hit would eat up about 25 percent of that.

Cowboys moving quicker this time, and that makes sense

According to Ben Grimaldi and other reports, the Cowboys and Prescott are expected to agree on a contract extension and largely viewed to be moving urgently on the deal. Ian Rapoport suggested they would agree on something, "before free agency."

The Cowboys need to get this done, and fast. Failing to do so would be a waste of a year for the Cowboys, as it would surely restrict them of any other opportunities to build a competitive team around Prescott.

Free agency starts March 13, giving the two sides less than a month to agree on something that will perhaps be the most foundational building block of the next decade for Dallas.

Furthermore, as we discussed earlier today, Prescott has all the leverage this time. He has a year left on his deal and clauses that prevent the Cowboys from exercising other options, like a trade or a tag of any sort.

The Cowboys need this done, and fast. And as a result, so too does Prescott, and the alignment of motivations there might be the single most important difference this time compared to last. They can't make the same mistake twice of dragging this out, because it'll be ridiculously more costly this time around.