When quarterback Dak Prescott pushed the Dallas Cowboys for a third consecutive playoff appearance in 2023, owner Jerry Jones was quick to hand him a league-high extension. However, after missing the postseason for two consecutive years despite one of Prescott’s best seasons, Jones is wondering if his gamble on the four-time Pro Bowler was for the best.

“This is a surprise to me,” Jerry Jones admitted on 105.3 The Fan this Friday. “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.

“So, we’ll make those kinds of adjustments that’ll give us the best shot at the playoffs. 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.”

Before the 2024 season opener, Jones approached his QB during a walkthrough and got a handshake deal done for a four-year, $240 million extension. Right then, he hoped Prescott would be the quarterback of the team’s future as long as he was there. But whether Prescott would be their franchise quarterback wasn’t the question that troubled Jones. He knew the writing on the wall: provide Prescott with the right tools.

He extended Prescott’s favorite target, wide receiver CeeDee Lamb, that same year. Still, the team ended that season with a losing record of 7-10. In 2025, Jones brought in George Pickens from the Pittsburgh Steelers. But we now know what became of the season after the WR’s arrival.

Under the first-year head coach Brian Schottenheimer, the offense ranks eighth overall, according to PFF. Moreover, they lead the league in yards and are fourth in points scored. Individually, the 32-year-old was voted for a Pro Bowl once again and has had an elite performance. The team, though, has suffered, missing playoffs with another losing year, with a 7-8-1 record.

Now, while one may consider the league’s 28th defense as the culprit for the losses, it might not exactly be their fault. Let’s look at their Christmas game against the Washington Commanders.

How the Cowboys’ offense kept failing

Prescott’s offense started strong, with three points in their first three possessions. By then, the Cowboys led 21-3. However, the offense soon sputtered. While Dallas’ defense failed to stop the Commanders and third-string quarterback Josh Johnson’s hopes for a comeback, their offense didn’t help either.

The QB did not score anything in the second half and punctuated the game by finding George Pickens for a 21-yard gain on third-and-1 with under two minutes left for a 30-23 win. The offensive performance overall was inconsistent, with Prescott having the eighth-lowest completion percentage of his career (51.4%) and a season-high sack count of six.

Top Stories

Cowboys Fire Defensive Coordinator Matt Eberflus: Contract, Salary, NFL Earnings & More

10 Biggest NFL Draft Busts of the Last Decade, Including Trey Lance and Justin Fields

Andy Reid Sets Record Straight on Travis Kelce’s Chiefs Future As Retirement Question Continue to Mount

Russell Wilson Announces Retirement Stance as Giants QB Shares Hidden Injury News

John Harbaugh’s Feelings Clear on Ravens’ Future as Firing Calls Mount Against HC

“We’ve got to do a better job of finishing,” Prescott said after that game. “This game could’ve stayed lopsided.”

The scoring performance was eerily similar to their second-half shutdown a week ago against the Los Angeles Chargers. So, while the Cowboys need to take a look at their defense, beginning with defensive coordinator Matt Eberflus, they also need to put more incentives into their offense.

In Prescott’s ten years with the team, the 32-year-old has helped the team to five postseason appearances. But with limited resources, he has been unable to provide the outcome that Jones expects from him.

Although Jerry Jones 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 winners in place. Still, if the team is finishing with a single-digit record, it’s time for some changes.

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 hints 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.

Jerry Jones reveals why he released Trevon Diggs

Losing Micah Parsons before the season even began hurt the defense. But Jerry Jones didn’t stop there. The next player out of Dallas is star cornerback Trevon Diggs. A couple of days after the Week 17 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 multiple causes.

Diggs tore his ACL in 2023, and since then, he has never been the same for the Cowboys. He missed six games in 2024. In 2025, he played just eight games, 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 incident 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.

Now, for the first time in years, Jerry Jones isn’t selling belief; he’s bracing Cowboys fans for what’s to come.