Will Cain asserts victory over Dan Orlovsky in ESPN debate
Yahoo Sports • 1 min read • Latest: Sep 29, 2026, 9:00 PM
Last updated Sep 29, 2026

Will Cain declared victory in a past sports debate involving Dak Prescott and Carson Wentz during a recent episode of The Will Cain Show. He recounted a years-long argument where he opposed Dan Orlovsky and other ESPN commentators, asserting Prescott's superiority over Wentz. Cain's stance is framed as a highlight of his career, particularly as Prescott has since secured a lucrative extension with the Cowboys compared to Wentz's struggles for a starting role. The discussion also touches on Orlovsky's later appreciation for Jalen Hurts.
- •Will Cain revisits an old ESPN debate about Prescott and Wentz.
- •Cain calls it one of his biggest debate victories.
- •Orlovsky once favored Wentz over Hurts, which he later reconsidered.
- •Prescott signed a $60 million yearly contract, while Wentz is currently a backup.
- 9:00 PMYahoo Sports — 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…
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