Cowboys Dak Prescott decision is cherry on top of terrible offseason for Jerry Jones

The Dallas Cowboys are redefining the meaning of going "all in." When owner Jerry Jones uttered that phrase, perhaps what he meant was that the Cowboys were going to fully commit to demolishing their current roster and reconstructing it after the 2024 NFL season. That's certainly what their actions suggest.

Cowboys fans are understandably frustrated by Dallas' inactivity at the start of free agency. Time and time again, it seems the Cowboys' plan of action is one of inaction, even if it means compromising the team in 2024.

The team doesn't have much salary cap to operate with, but they could have created cap space by signing quarterback Dak Prescott to a contract extension. Instead, it seems Dallas is content with allowing Prescott to play out this season on his current deal and hit the free agency market in 2025. That's not good for either party in 2024.

Dallas Cowboys seem prepared to let Dak Prescott enter free agency in 2025

Prescott is entering the final year of a four-year, $160 million deal signed in March 2021. The Cowboys cannot franchise tag him in 2025, so he will become a free agent next spring.

Prescott's contract contains a provision that prevents Dallas from designating him as a franchise or transition player in 2025, which means he would be free to leave the team in free agency if he plays out the upcoming season on his current contract. The Cowboys must decide on Prescott's future prior to the 2024 season, or they risk losing the quarterback in free agency with no compensation.

At the time his current contract was signed, Prescott's $40 million per year deal was the second-richest in the NFL. Since then, Dallas has restructured the contract on four separate occasions, with the most recent restructure resulting in a $55.4 million salary cap number for the 2024 season — the second-highest salary cap hit in the league behind Cleveland Browns quarterback Deshaun Watson ($63.9 million).

It's possible Prescott has held the Cowboys hostage, hoping to leverage his salary cap number and solid regular season to sign a record-breaking contract. In that case, it would make sense why Dallas apparently aren't willing to commit long-term. Still, Prescott's contract and cap figure is a situation they put themselves into.

To make matters even worse, the void years they added to his contract in his latest restructure will cost Dallas more than $50 million if Prescott leaves in free agency next year. Signing him to an extension prior to the void would help them control the dead cap hit, but that only gives Prescott more leverage in negotiations.

Either way, a disastrous offseason hasn't set up Prescott and the Cowboys for success. The franchise has faced significant scrutiny for their decisions during free agency. Instead of re-signing running back Tony Pollard, the Cowboys allowed him to enter free agency without a viable veteran option. When Dallas had the chance to sign star running back Derrick Henry, they declined to pursue him. As running backs such as Henry, Saquon Barkley, D'Andre Swift, Josh Jacobs, and Aaron Jones were scooped off the market, the Cowboys barely made a move.

Wide receiver CeeDee Lamb, who earned first-team All-Pro honors, is also entering a contract year, while 2021 NFL Defensive Rookie of the Year Micah Parsons is eligible for a contract extension this offseason. The Cowboys chose not to extend Lamb and released wide receiver Michael Gallup for cap space. Cowboys linebacker Leighton Vander Esch said his emotional goodbye to Dallas last week, but at least the team brought in linebacker Eric Kendricks — their lone external free-agent signing.

The 2023 NFL season may have been the Cowboys' best shot to capture their elusive sixth Super Bowl championship. Despite their postseason meltdown, the Cowboys had talent across their roster. Nine Dallas players earned first- or second-team All-Pro honors. 

Hope is starting to run out — 28 years have gone by since Dallas last won a Super Bowl.

How bad have things gotten? Future Hall of Fame left tackle Tyron Smith, who spent the past 13 seasons as a franchise pillar in Dallas, believes the New York Jets give him a better chance to win the Super Bowl than Dallas does. And he may be right.

"And for the way things were looking in Dallas, I knew it was most likely going to be the Jets," Smith said. "Honestly, I got excited for a new chapter in my life."