Many celebrated Dak Prescott striking an extension deal with the Dallas Cowboys. But there are also others who are left scratching their heads, including Skip Bayless. The former “Undisputed” personality did not hide his emotions when he launched into a tirade over Dallas franchise owner Jerry Jones' decision to make Prescott the highest-paid player in the history of the National Football League.

“Jerry Jones just made a QB who has stunk in 3 straight playoff losses – who is 2-5 in playoff games – the highest paid player in NFL history,” Bayless went off in a rant he posted on X (the social media platform formerly known as Twitter).

“This is why Jerry's Dallas Cowboys have not even made it to an NFC Championship game in going on 30 years. Now I'm … STUCK WITH DAK.”

The Cowboys put an end to the offseason saga regarding the status if Prescott with the team when they inked him to a monster four-year contract extension worth $240 million. That checks out for a huge average annual value of $60 million. It easily clears some of the other massive AAV of previous quarterback deals in the league involving the likes of Joe Burrow of the Cincinnati Bengals, Jordan Love of the Green Bay Packers, and Trevor Lawrence of the Jacksonville Jaguars.

Bayless continued to lament the current status of the Cowboys as he perceives it to be.

“Since I was 10 years old, I have loved the Dallas Cowboys with all my heart and soul,” an impassioned Bayless said.

“But right now that love is being tested like never before. If you're a smart Cowboy fan, you know the feeling.”

Dak Prescott leads the Cowboys to Week 1 win after signing extension

Dallas Cowboys quarterback Dak Prescott (4) celebrates after a touchdown during the first half against the Cleveland Browns at Huntington Bank Field.
Ken Blaze-Imagn Images

Prescott reciprocated the expensive gesture from the Cowboys by having a solid performance in Sunday's 33-17 win on the road against Deshaun Watson and the Cleveland Browns. In that game, the former Mississippi State Bulldogs star went 19-of-32 for 179 passing yards and a touchdown with zero interceptions. He was sacked three times for a loss of 16 yards, but at least Dallas came away with a comfortable victory.

Bayless can still change his mind about Prescott, but that will heavily depend on how much success the Cowboys will have with the quarterback at the helm of the team's offense. The Cowboys have made the playoffs in each of the last three seasons but they never progressed past the divisional round over that stretch. That's a disappointing series of results for Dallas, especially when considering the fact that they have won 36 games in that span.