Dallas Cowboys executive vice president Stephen Jones recently expressed that the franchise “absolutely” wants to sign quarterback Dak Prescott, who’s entering the final season of a four-year, $160 million deal, to a long-term deal.

Is that the right approach for Dallas to take?

On Wednesday’s edition of “Undisputed,” cohost Skip Bayless vehemently disagreed with the notion that the Cowboys have to retain Prescott.

“[The Cowboys] will be just good enough to get annihilated in some playoff game. That’s what happens year after year after year,” Bayless asserted about the prospect of the Cowboys potentially sticking with Prescott past 2024. “There’s some little thing missing if [the Cowboys] want to go to the promised land. After a while, 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 … 

“Dak Prescott takes you to the precipice, and then you fall off the cliff.” 

Fellow cohost Keyshawn Johnson was incredulous about Bayless’ take, arguing that Prescott isn’t the center of the Cowboys’ continual shortcomings.

“You can’t sit here and blame it on Dak Prescott,” Johnson said. “What you do too much, Skip, is you try to point the finger at Dak when [the] defense isn’t playing well, [they’re] not running the football well, [the] offensive line is in and out of the lineup because they can’t stay healthy, [the] coaches are making bad decisions at times, calling timeouts at the wrong time, not calling timeouts when they’re supposed to, throwing the football when they supposed to be running it, running it when they supposed to be throwing it. 

“But you wanna blame Dak for all of this when the owner just sat there and said ‘when Dak Prescott is our leader, and he’s in the building, and he’s a part of this team, we all feel good.’ … who the hell you gone get?”

Prescott totaled 4,516 passing yards, an NFL-high 36 passing touchdowns, nine interceptions and a 105.9 passer rating, while completing a career-best 69.5% of his passes last season. He also ran for 242 yards and two touchdowns. As a whole, the Cowboys averaged 258.6 passing yards (third in the NFL), 112.9 rushing yards (14th), 371.6 total yards (fifth) and 29.9 points (first) per game.

The Cowboys finished the regular season 12-5, winning the NFC East for the second time in three years. That said, they lost at home to the Green Bay Packers in the NFC wild-card round, trailing 27-0 at one point in the first half and trailing by as many as 32 points.

Cowboys confirm plans to extend Dak Prescott: will the investment pay off?

Dallas owns a combined 73-41 regular-season record with Prescott as its starter but is just 2-5 with him in postseason play. A loss at home to the Packers in the divisional round in the 2016 season, a divisional round loss to the eventual NFC-champion Los Angeles Rams in the 2018 season and back-to-back losses to the San Francisco 49ers in the 2021 wild-card round and 2022 divisional round are the other playoff defeats the Cowboys have suffered with Prescott under center.

Prescott, 30, is a three-time Pro Bowler who won 2016 NFL Offensive Rookie of the Year honors. He also won the 2022 Walter Payton NFL Man of the Year Award.

The Cowboys haven’t reached the NFC Championship Game since the 1995 NFL season.

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