Stephen A. Smith keeps winning.
Monday’s edition of First Take was predictably soaked in Dallas Cowboys hate, but on top of ripping Cowboys fans’ hearts out, Smith also took panelist Marcus Spears’ money and pride by claiming his winnings on a bet the two made over whether Dallas QB Dak Prescott would throw two interceptions on Sunday Night Football.
After Smith opened the show by donning former Cowboys receiver Michael Irvin’s No. 88 jersey and making fun of Dallas’ lack of a “playmaker,” he embarrassed another former Cowboy in Spears by airing out the bet Spears lost.
“(Spears) said I was being disrespectful and I’m going to owe (Prescott) an apology,” Smith said. “What you got?”
The First Take crew discussed how Stephen A Smith should accept payment from Marcus Spears on their $1,000 bet that Dak Prescott would throw two interceptions versus the Niners (he threw three) pic.twitter.com/d0MFeTNcZA
— Awful Announcing (@awfulannouncing) October 9, 2023
Dan Orlovsky and Shannon Sharpe then proceeded to debate how Spears should pay Smith. Orlovsky suggested airing the exchange live. Sharpe wanted Spears to pay up in quarters for maximum embarrassment. Smith prefers Cash App.
Admittedly, Orlovsky’s suggestion feels best. Spears is so often broadcasting remotely that making him fly to New York City to come to the First Take studio, sign a check, and hand it to Smith live would be great television.
Orlovsky certainly looked like a man who understood the content value the show had on its hands during the segment:
Dan Orlovsky couldn't have been giddier to learn about this development pic.twitter.com/V9BmmChaOK
— Awful Announcing (@awfulannouncing) October 9, 2023
He may have a future as a First Take segment producer if the NFL analyst thing doesn’t work out.
The Cowboys are the gift that keeps on giving for Smith (except when his guests go too far). Especially as more and more former Cowboys join sports media and get to also be the butt of his jokes, rather than just Dallas fans getting cooked.

About Brendon Kleen
Brendon is a Media Commentary staff writer at Awful Announcing. He has also covered basketball and sports business at Front Office Sports, SB Nation, Uproxx and more.
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