It was the chilling winter of 2023, the last time the Dallas Cowboys made the playoffs. Even then, they didn’t move it past the Wild Card round. Fast forward to today, Jerry Jones’ team has endured two seasons back-to-back of playoff-free football. In fact, it’s been nearly a decade since the Cowboys advanced to the divisional round. The one constant through this drought? Dak Prescott.

Jones rewarded the quarterback with a historic four-year, $240 million extension in 2023, believing he’s the best player to lead America’s team to the Super Bowl. Prescott became the highest-paid player in the league’s history, but Dallas finished 2024 with a single-digit record. Now, with the team standing at another disappointing 7-8-1 and officially eliminated from the hunt, the billionaire owner is finally facing the music. Perhaps his biggest bet, the one on Prescott, hasn’t paid out.

“This is a surprise to me,” Jerry Jones admitted on 105.3 The Fan. “When I signed Dak [to his most recent contract extension], I didn’t expect for us not to be in the playoffs the last two years.”

Although he admitted that Prescott lacked enough “protection” on the field, he believes the offense was built to score this year. There were defensive issues, which the Cowboys “slipped this year” following Micah Parsons’ trade; they still have “bones” of winners in place. Still, if the team is finishing with a single-digit record, it’s time for some changes.

“So, we’ll make those kinds of adjustments that’ll give us the best shot at the playoffs,” Jones added. “We can’t be timid about it. They’re not just subtle, little adjustments. We’ll have to do some things that, as they say, put your head between your legs, and prepare for some rough landings.”

Though Jones didn’t explicitly mention that the changes would come at the quarterback position, his honest assessment of his team’s failures following Prescott’s massive extension does indicate towards it. For now, the starter for Week 18 is going to be the four-time Pro Bowler, but head coach Brian Schottenheimer could reduce his playing time and bring backup Joe Milton on the field.

There remains one week before the Cowboys officially begin their offseason, and the 83-year-old owner has already started with his promising changes.

Why did Jerry Jones release Trevon Diggs?

The first player off Dallas is star cornerback Trevon Diggs. A couple of days after Week 17’s game, the Cowboys took the drastic step of waiving the All-Pro cornerback. Head coach Schottenheimer described the move as a “culmination of events,” but the final act of the messy divorce involved a failed defense, disobeying the team’s standards of recovery, and an infamous Christmas night concert.

Diggs tore his ACL in 2023, and since then, he has never been the same for the Cowboys. He missed six games in 2024 and played just eight games in 2025, where his stats of interceptions and pass breakups were nil. This happened two years after the Cowboys signed him to a massive $97 million extension.

Adding to the tension was a bizarre concussion in October. He reportedly revealed that the concussion was a result of a home accident when a TV mounting pole fell on his head while he was trying a DIY home project. Then, there was the infamous Christmas following the Cowboys’ victory over the Commanders.

Diggs asked Schottenheimer for permission to stay behind with his family. His request was denied, but he stayed anyway. It was later revealed through photos that he attended Shy Glizzy’s concert at the Howard Theatre. As if these weren’t enough, he had also incurred a $500,000 fine for skipping team rehab earlier in the year. So, it was indeed a culmination of events that led Jones to take the drastic steps.

And for the first time in years, Jerry Jones isn’t selling belief; he’s bracing Cowboys fans for the cost of being wrong, and the bill is finally coming due.