"Shame on Jerry and Stephen Jones": Skip Bayless unleashes fury on Cowboys owners following Dak Prescott's contract extension news

The Dallas Cowboys are expected to sign quarterback Dak Prescott to a contract extension this off-season and he could become the highest-paid player/quarterback upon signing his new deal.

Prescott is entering the final year of his current contract, which pays him $59.5 million, in the 2024 season. The Cowboys would like to reduce that number, and the easy way will be to sign Prescott to a new long-term contract.

After hearing that Dallas is expected to keep and extend Prescott, Skip Bayless, a lifelong Cowboys fan and host of Undisputed, criticized owner Jerry Jones and GM Stephen Jones for committing to Prescott for another four or five years.

"So I will be mired in misery for the next God knows four years, five years, whatever it is, and you will come in here gloating Sunday after Sunday because we will be just good enough to get annihilated in some playoff game," Bayless said.

"It's like the old saying, you fool me once shame on you, fool me twice—shame on me. Fool me three times, shame on Jerry and Stephen Jones because they are shaming and shaming and shaming us. Because we're throwing good money after bad."

Here are the comments Jerry Jones made earlier this week when asked if the team has thought about life without Prescott:

"Our whole thing with Dak is him being a Cowboy. That's all that's on our mind [We] certainly don't get into those type of thoughts."

How far has Dak Prescott gotten the Dallas Cowboys during his tenure as quarterback?

Dak Prescott during Philadelphia Eagles vs. Dallas Cowboys

It's no wonder Skip Bayless is disappointed that the Dallas Cowboys will likely extend Dak Prescott for another four to five years. He hasn't won anything big.

Prescott has led the Cowboys to the postseason in five seasons. However, he has failed to reach an NFC Championship game, let alone the Super Bowl. Three of the five times, the Cowboys didn't even win a postseason game. He has a 2-5 postseason record in his career.

Prescott has been a solid quarterback, making three Pro Bowls and one All-Pro selection, but he hasn't been a top-five quarterback since entering the NFL.

If Dallas manages to win one Super Bowl in the next five years, only then will Bayless be satisfied with Dak's services.

If you use any of the above quotes, please credit Skip Bayless, Undisputed, Jerry Jones, Around the NFL, and H/T Sportskeeda