The 3 options the Cowboys have when it comes to Dak Prescott and his new contract extension

The Cowboys front office has some options, but which one will they choose?

The Dak Prescott contract extension saga is something that will be discussed ad nauseam this offseason as the Dallas Cowboys must decide what to do with the most important player on the roster. There will be many different ideas about how it should be handled and opinions about what he’s worth. The conversations will be endless, so we might as well get used to it.

For some of us, this ordeal is rather straightforward. It feels like we already know what is coming down the pike, it’s now only a matter of when it happens.

While we may think we know how it’s going down, we should try to keep an open mind and look at every possibility, and that is what we are going to do today. We have narrowed the Dak dilemma into three possible options for the Cowboys front office.

OPTION 1: SIGN HIM TO A NEW EXTENSION IN MARCH

The simplest way to take care of business is to just do the deed and get a new deal done before the start of the new NFL season, which begins on March 13th. The reason for this target date is that an extension would reconfigure Prescott’s contract and free up a large part of the $59.5 million cap hit that is currently on the books for this season. Working a deal at that time would allow the Cowboys to be players in free agency as they would have money cap space to work with.

For this to happen, both sides would need to reach a deal they are happy with. It’s important to note that Prescott’s price is his price. There isn’t any advanced business negotiation sorcery that is going to allow Jerry Jones to get him on a discount. Prescott’s agent, Todd France, is going to get the best deal possible for his client. If they can reach an agreement that both sides are happy with, then Bazinga, the deal’s done, and we can put this whole thing to rest. If not, it’s time to move on to plan B.

OPTION 2: CONVERT BASE SALARY INTO BONUS AND EXTEND HIM IN SEPTEMBER

If the Cowboys and Dak can’t get a deal done in March, it’s not the end of the world. The front office has another option available that will essentially serve the same purpose while buying them a little time. The Cowboys can continue to do what they’ve done every year since Prescott signed his last deal and that’s converting most of his base salary into bonus money. This is just a bookkeeping maneuver to spread that base salary out over multiple years. Since Prescott has two void years on his contract, the Cowboys can spread a great majority of his $29 million base salary across three years, 2024, 2025 (void), and 2026 (void).

This, along with other looming restructures, will give the Cowboys room to operate in free agency as you can see from the above image which players are occupying the most cap space at the moment. Pulling the trigger on a Dak restructure could show that both sides are “too far apart” in negotiations and create the perception that the Cowboys are considering entering the season without giving Prescott a new deal. Prescott and his agent would need to decide just how comfortable they are playing another season without any future guarantees. He’s coming off an MVP-caliber season right now where his stock is high. What’s it going to be a year from now when other variables enter the equation, which may include a drop off in play, another playoff disappointment, and the risk of injury to his soon-to-be 31-year-old body? These variables could be enough to push the sides close enough together to get a deal done in the final hours before Week 1 kicks off on the 2024 season.

OPTION 3: CONVERT BASE SALARY INTO BONUS AND DON’T EXTEND HIM

If the Cowboys convert the maximum amount of his $29 million base salary into bonus, this is what happens…

The Cowboys’ 2024 cap hit from Dak drops from $59.46 million to $40.93 million, freeing up $18.53 million in cap space. That’s the good news. The bad news is that the Cowboys will still be on the hook for the remaining $55 million (of his original $160 million) spread across the two void years of his contract ($35 million in 2025, and $20 million in 2026). If they don’t end up extending Prescott, that will be a hefty tax to pay for an asset who will be playing for some other team after the 2024 season.

The Cowboys have the flexibility to delay an extension with Prescott until the fall and doing so will give them a full training camp with Trey Lance. When September rolls around, they will have a better sense of Prescott’s value to the team. Would they be comfortable transitioning to Lance and letting Dak walk after the 2024 season? Or would Lance’s skills bring too much doubt and force their hand to re-up on Prescott? These questions will be a lot easier to answer in the fall.

Should Dak not have a new contract when the season starts, the Joneses will continue to give us lip service about how Prescott’s still their guy and that they will revisit things in the offseason. This will be a weak attempt to not burn that bridge should Prescott set the league on fire and have an incredible 2024 season. But rest assured, the damage will be done. Not getting a deal done by the start of the season will likely sour the relationship between Dak and the front office and you better believe Prescott’s contract demands will be enormous next offseason as he holds all the cards.

Gone are the days when they could franchise tag him to prevent him from entering the open market. A more likely scenario is that Prescott takes matters into his own hands and waives his no-trade clause so both sides can wash their hands clean of the situation and move forward.

Are any of these options desirable to you? Is there another choice we’re overlooking? If so, let us know in the comments.