Will Cain declares victory over Dan Orlovsky

Dak Prescott hasn’t won much for the Dallas Cowboys during his NFL career, but he won an old ESPN argument with Will Cain.

Before he debated political matters on Fox News and after he debated political matters on CNN, Cain debated sports matters on ESPN. And recently, Cain revisited one of those matters to declare victory. The matter? Carson Wentz.

The topic was revisited on Will Cain Country Monday afternoon, when Fox News columnist David Marcus referenced Wentz, prompting Cain to call out those who used to argue the current backup quarterback for the Minnesota Vikings was better than Prescott.

Will Cain Reacts to His Biggest Sports Media Debate Win@willcain and guest @BlueBoxDave look back on one of the most famous sports media debates surrounding Carson Wentz and Dak Prescott.

Will breaks down his classic clash against Dan Orlovsky and ESPN analysts, declaring his… pic.twitter.com/26wWrQSiCy

— The Will Cain Show (@WillCainShow) September 28, 2026

“Carson Wentz, I have had that debate, I had that debate for years,” Cain recalled fondly. “And I probably don’t have any greater victories on my ledger than that. It was me against the world. Me against Dan Orlovsky and every other commentator on ESPN. And who won that one? Dak or Carson Wentz? Thank you. I think that one is my Super Bowl.”

Orlovsky even recently admitted his fondness for Wentz caused him to appreciate Jalen Hurts only after a delay. Wentz over Hurts didn’t age well; neither did Wentz over Prescott. But Prescott over Wentz did.

There was that brief moment in 2017 when Wentz was an MVP candidate, and Prescott seemed to be in a bit of a sophomore slump. Then, years later, Wentz struggled to find a backup gig while Prescott signed a contract extension with the Dallas Cowboys worth $60 million a year.

Cain had some losses during his time on ESPN, although he never actually waved the white flag to Bomani Jones. But Cain also had some wins at ESPN, and aligning with Prescott over Wentz was certainly one of them.