Jerry Jones didn’t become a billionaire by making bad financial decisions. But after months of back-and-forth talks with Dak Prescott, Jones faces tremendous pressure to get a deal done with his star quarterback before time runs out. And with each passing second, that only adds to the uncertainty of the future of the Dallas Cowboys.

Will Prescott agree to a long-term contract extension before the July 15 deadline? Only Jerry Jones can make that happen. So now, the 77-year-old is about to reveal his true feelings on his star QB with his impending contract deadline.

Dak Prescott’s contract situation has loomed large in Dallas

Dating back to before the 2019 season, Jerry Jones has had to answer questions about Dak Prescott’s contract. The former fourth-round pick bet on himself and turned in an excellent campaign. Of course, he needed to after turning down a lucrative offer prior to the season.

Of course, the Cowboys went just 8-8 and didn’t qualify for the playoffs. For all of Prescott’s impressive accomplishments, his inability to lead Dallas on ad deep playoff run sticks out like a sore thumb.

Still, that hasn’t stopped Jones from trying to sign the two-time Pro Bowler to a contract extension. However, despite some substantial offers, Prescott has yet to put pen to paper. The Cowboys did utilize the franchise tag to retain his services, but that should have simply been a stop-gap solution with the eventual goal of signing a multi-year extension.

Jerry Jones is running out of time to sign his quarterback to a long-term deal

Unfortunately for Cowboys fans, every second that passes without news of a long-term deal for Dak Prescott only adds more uncertainty to the future of the franchise. And very shortly, Jerry Jones will have to make the biggest financial decision of his life.

Based on the CBA rules, any player who is currently under the franchise tag has until 4 p.m. on July 15 to sign a multi-year contract extension. If not, the player must play out the season on the franchise tag tender.

That puts tremendous pressure on both parties to sit down and give every effort to come to an agreement. For Jones, that could mean sacrificing his preference for more years on the deal. For Prescott, it could mean settling for top-five quarterback money rather than a record-setting deal.

Either way, that 4 p.m. deadline on July 15 looms large for both Jones and his star quarterback.

Jones will reveal his true feelings with Prescott’s contract

From the Cowboys perspective, it makes sense to not hand Prescott a record-setting deal. He has put up solid regular-season numbers, yet the Cowboys have won just a single playoff game in the last four years. Does that warrant a deal with $100 million guaranteed?

Some might put the playoff failures on former head coach Jason Garrett. However, quarterbacks get paid to win in the playoffs, and Prescott simply hasn’t done that.

On the other hand, you could make the case that the former SEC star still has untapped potential. He boasts a dynamic skill set to go along with a dangerously deep cast of weapons. With Mike McCarthy on board, it wouldn’t be surprising to see Prescott’s numbers explode in 2020.

So what’s a fair deal for the fifth-year pro? Patrick Mahomes just signed a $503 million deal. But for Prescott, a more realistic contract should put him somewhere near Russell Wilson’s $35 million annual salary. That still seems like an overpay considering Wilson has a Super Bowl ring and has sustained success over a longer period of time, but that’s about the ballpark.

However, if Jones fails to find a middle ground, he risks losing everything he has built over the last few years. Dallas can franchise tag Prescott again next offseason, but what kind of message does that send to the team? The Cowboys have a franchise-caliber quarterback already on the roster and have surrounded him with elite weapons.

Failing to lock Prescott up on a multi-year deal means potentially having to find another quarterback a year or two from now. Is that the route Jones wants to take?

Ultimately, Dak Prescott deserves a raise. Nobody doubts that. Whether he gets it on a one-year franchise tag tender or through a multi-year deal rests solely with Jerry Jones. But after months of negotiations, the powerful NFL owner has little time left on the shot clock. Will he surprise everyone and ensure Prescott remains a long-term fixture in Dallas?

We’ll know by 4 p.m. on Wednesday.