Dan Le Batard Pulls Off Massive Upset Of Mark Cuban In Woke All-Star Challenge

The 2024 Woke All-Star Challenge Sweet 16 is officially set after a wild play-in round that saw Dan Le Batard pull off one of the bigger upsets in recent Woke Challenge history. 

With 50.4% of the vote, Deadspin supporter Le Batard took out DEI backer Mark Cuban in a matchup that historians will be talking about for years to come. Just like in the NCAA Tournament where bracket makers will force a head coach to face his old school, we have a wild scenario where No. 1 seed Deadspin (featuring Carron J. Phillips who, experts say, helped kill Deadspin with his Chiefs blackface reporting, and wokester Julie DiCaro) will now face Le Batard in a MASSIVE WOKE Nonbinary Region showdown. 

Sweet 16 voting begins Thursday morning before March Madness tips-off. 

In the other play-in matchups, Mike Florio held strong in a battle with ESPN woke RG3 who performed better than expected in his rookie year. Mina Kimes won her matchup over ESPN woke extremist Elle Duncan and now moves on to face stalwart Dawn Staley in the #MeToo region. 

Finally, we have Joy Reid kicking Don Lemon's ass in the Gaslight Region. She'll now take on woke darling Rex Chapman, who finished runner-up in the 2023 Woke Challenge. 

The field is set. Now it's time to get to work finding a champion. 

That starts Thursday morning right here on OutKick. 

Buckle up. 

Written by
Joe Kinsey is the Senior Director of Content of OutKick and the editor of the Morning Screencaps column that examines a variety of stories taking place in real America. Kinsey is also the founder of OutKick’s Thursday Night Mowing League, America’s largest virtual mowing league. Kinsey graduated from University of Toledo.