2023 Woke All-Star Challenge: The Championship

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It’s Championship Monday here at OutKick where we’re about to determine who goes up on the Mount Rushmore of Woke.

Two wokes enter the 2023 Woke All-Star Challenge on top of their game, but only one winner (loser) can take home the hardware and join past winners (actually losers) Jemele Hill and Keith Olbermann as past champions who are so woke that they’ve been retired from competition.

Will it be Rex Chapman, making his second straight trip to the finals, joining his archnemesis Olbermann (Keith put and absolute hoodrat beating on Rex in the 2022 Challenge) on the mountaintop?

Or will it be Bomani Jones, who made the tournament as a No. 4 seed and had to win a play-in round, winning a title that he will immediately post to his Linkedin resume?

Keep in mind Rex absolutely throttled Kendrick Perkins in the Final Four while Bomani had a fierce battle against Steve Kerr that went to a recount because it was so close.

There’s nothing more to say here. It’s time to let these titans battle it out for woke supremacy.

Let’s get it on!

  1. Voting will consist of Twitter polls and one other online poll for those who refuse to use Twitter.
  2. Our voting system is the most secure, and most respected in the online bracket industry; there will be no shenanigans or ballot harvesting here.
  3. Voting will run for 24 hours. That’s it. Our director of voting will drop the hammer at 24:00:00.
  4. No purchase necessary.


Written by Joe Kinsey

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.

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