The Dallas Cowboys are going to pay Dak Prescott a lot of money. The only questions are when is it going to happen, and how much will it ultimately cost the team? It’s hard to know the “when” as Jerry and Stephen Jones are really good at holding their breath as long as they can in order to keep that asking price down as much as possible. A penny saved is a penny they can use to help retain another key player from this talented football team.

It’s a little easier trying to figure out the “how much” part as we have somewhat of a idea with recent contract extensions of Carson Wentz and Jared Goff. Back in June, Wentz signed a four-year, $128 million extension, worth $108 million in total guarantees. He received a $16 M signing bonus, with $66 M guaranteed at signing.

A couple weeks ago, Goff signed a four-year, $134 million extension, worth $110 million of total guarantees. He received a $25 M signing bonus, with $57 M guaranteed at signing, and an average annual salary of $33.5 million.

While Dak’s contract ultimately will be different, these numbers do provide a baseline as to what Prescott’s new contract may look like. To make the prediction at Prescott’s new deal, I’m considering the following:

Prescott’s extension will be for five years, not four. Unlike Wentz and Goff, Dak doesn’t have a fifth-year option exercised, so adding that extra year puts Prescott under contract through the year 2024 just like these other two guys.

Dak’s getting more money. You can attribute it to the “highest paid” theory as one of the advantages of being last, or you can justify it by the fact that he’s just performed better than the other two so far at this point in their careers. Wentz and Goff went first and second overall in the 2016 NFL Draft, versus Prescott who went 135th overall, but none of that matters now. People see Wentz and Goff as having more potential to be great because of their draft pedigree, but let’s not forget that they’re not the only young quarterback that’s allowed to improve. Prescott is already showing what he can do under the tutelage or new QB coach Jon Kitna and offensive coordinator Kellen Moore.

Prescott’s getting a bigger signing bonus. Call it a good gesture from the Joneses for a little retroactive compensation. Because of when he was drafted, Dak’s earnings have been incredibly low compared to these other guys, so a little more money up front is a nice way to show their gratitude for patiently going to work each day and being a consummate professional.

With those things taken into consideration, let’s give Dak Prescott a five-year, $169 million extension, worth $117 million in total guarantees. He should get around $30 million in signing bonus, with $64 million guaranteed at signing and an annual average salary of $33.8 million. A side by side comparison of these three is as follows:

Prescott comes out ahead in almost every category. Is it wrong to believe he should be paid more than these other two? When you consider the improvement he’s shown, the potential of this offense with better play-calling, and the strength of the Cowboys new receiving group - Prescott may end up being one of the top quarterbacks in the league.

Breaking down Dak’s potential new deal should look something like this:

Prescott should get close to $64 million guaranteed at signing which will include his $30 M signing bonus, his 2019 and 2020 base salary, plus his $21 M roster bonus that should be paid in March of 2020.

Prescott’s guarantees will continue to accrue on the third day of each new season. If he’s still on the roster in March of next year, his 2021 salary will be fully guaranteed. And subsequently, his 2022 salary becomes fully guaranteed in March of 2021, racking up his total guarantees near $117 million.

The biggest cap hit for the Cowboys would come next season which is great considering they are one the teams with the most cap space in 2020, with over $80 million available. This keeps Dak’s cap number a little more reasonable down the line. And considering how the salary cap continues to grow, this cost won’t be so constraining. This affords them the luxury of keeping other players under contract as well. That’s good business.

The Cowboys escape hatch for this deal comes after the 2022 season as they could get out of the final two years of his deal with just a $6 million dead money hit.