More doubt cast upon Dak Prescott's future with Cowboys beyond this season

As the regular season approaches, it is seeming more and more likely that the Dallas Cowboys will not be able to retain franchise quarterback Dak Prescott beyond this season. He is entering the final year of his four-year deal worth $40 million annually. Jeff Kerr wrote about it for CBS Sports in his NFL pre-training camp overreactions and reality checks article. He views Prescott leaving as the reality.

It is a combination of things that have led to this point for Prescott and the Cowboys. There has been very little dialogue, if any, about getting him an extension. Unless something manifests very quickly, Prescott will almost certainly be hitting free agency after this season. For a quarterback of his caliber, we are looking at a deal somewhere in the $52 million range, possibly even higher than that for him.

Another huge factor is that Dallas still needs to figure out how to pay wide receiver CeeDee Lamb before his free agency as well. Let's not forget that pass-rusher extraordinaire Micah Parsons is in the penultimate year of his rookie contract. Almost always getting lost in the shuffle, future Pro Football Hall of Fame guard Zack Martin is in the final year of his contract, too. He may retire, but he can walk.

Outside of the Cowboys' awful contract situation, it is also the final year of Mike McCarthy's deal.

This is all culminating in a season where the Cowboys have no choice but to win, but will they?

Future looks bleak on Dallas Cowboys' chances to retain Dak Prescott

Look. This really isn't any new information, but rather a glimpse into how it lands within the NFL calendar. I don't know what Dallas has been doing all offseason long, but it really feels like they are falling asleep at the wheel with it. This feels like Dallas' best chance to win Jerry Jones one more Super Bowl because they don't seem to be setting themselves up for success beyond this season.

It is frustrating to not have any idea how a team will look one year from now. For a team that is rebuilding or about to hit the reset button, this kind of contractural uncertainty is merely par for the course. However, Dallas has been a playoff-caliber team throughout Prescott's time with the franchise. Unless he gets hurt or plays terrible, somebody is going to pay him, but will it be Dallas?

While there are plenty of quarterbacks conceivably entering the 2025 NFL Draft, including the son of a former Cowboys great, you should not be counting your chickens before they hatch. Then again, that is just the Cowboys' way to some degree. Always one to put the cart before the horse, the only thing for certain about this year's team is that it will somehow find a way to disappoint its fan base.

For as long as Jones is the owner, it will be more about him than about his team hoisting Lombardis.