“I’m not gonna put a timeline on it, but I’ll be ready for the first game and when anything matters and very, very ready,” the Dallas Cowboys QB said. Dak Prescott’s career has been a paradox of NFL excellence and playoff heartbreak. The Cowboys QB puts up monster numbers. He’s a three-time Pro Bowler and the guy who led the league with 36 TD passes in 2023. But the problem is when the lights get brightest, the results vanish faster than a Cowboys lead in that year’s playoffs. One playoff win since 2018. That brutal Wild Card exit to San Francisco? A 23-17 rock fight where Prescott’s final drive died at the 40-yard line.

For all his regular-season heroics, Prescott’s legacy is stuck in neutral – a QB who’s too good to replace but not clutch enough to silence the critics. And now, with a league-high paycheck and zero Super Bowl rings, the pressure is reaching DEFCON levels. So much so that a former NFL QB thinks Jerry Jones’ $240 M megadeal for Dak Prescott might turn out to be his most expensive mistake.

Enter Chris Simms, who recently appeared on The Dan Patrick Show. In conversation with Patrick, Simms didn’t just put Prescott on his ‘most pressure-level‘ list. He torched the Cowboys’ golden boy.“I don’t think there’s more pressure than anybody in football than Dak Prescott,” Simms said flat out. “You’re the highest-paid quarterback in the league… I don’t think you’re one of the top 10 quarterbacks in football.”

Dak Prescott’s $240M elephant in the room has been quite a topic to debate in the league for now, at least until the QB shows his magic. The Cowboys’ star inked that monster extension last year with $231M guaranteed money. Only to blow out his hamstring by Week 9,  and watch the season crumble without him, 7-10.

This rollercoaster perfectly encapsulates why Simms’ recent comments on The Dan Patrick Show cut so deep. He sees the Cowboys as a team with a talented roster being held back by inconsistent QB play when it matters most. “I do think the team is a little more talented than the public is giving it credit for. They could be a surprise playoff team,” the 44-year-old admitted. And then Chris dropped the dagger, “The most stellar thing the last few years has been the amount of zeros on his contract.” Yes! The zeros, especially in his $ 240 M.

The Dak Prescott paradox

Chris Simms has never been one to sugarcoat his opinions. And when it comes to the Cowboys QB, he’s doubling down. Just last month, the former NFL QB took another swipe at Dallas’ $240 million man during an appearance on Up & Adams. And his take was just as brutal as his recent comments on Dan Patrick’s show.

“Dak Prescott is one thing that you would say, ‘What is holding them back?'” Simms said bluntly. “I don’t wanna say he’s holding them back, but he is the highest-paid player in football, and I would say he’s not near the top-5 quarterback in football… Is he even a top-10 quarterback? I don’t know about that, either.“

But here’s where it gets interesting. The Cowboys did make moves this offseason, restructuring Prescott’s deal to free up cap space. They also added another weapon on the offense. Welcome, Steelers WR George Pickens. Simms acknowledged the importance of that shift, saying, “Their offense was so just all, ‘CeeDee Lamb, CeeDee Lamb.’ And that’s cool, but when you play the really good teams, they know how to take away a player like that. Now they have another answer.”

So, Jerry Jones this time gave Dak what he needed: more help. Now, the spotlight burns even brighter. If he can’t deliver when it matters (read: January), then Simms’ criticism won’t just be an opinion; it’ll be the undeniable truth. Because Prescott’s stats look pretty until you see the December collapses and playoff no-shows. That $240M contract, right now, is buying more memes than wins. 

And in Dallas, where patience wears thinner than the ice in Jerry’s bourbon glass, that’s a problem Dak can’t afford to ignore.