The 2023 Woke All-Star Challenge Sweet 16 – Vote Now!

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Which woke will see she/he/her/his dreams come true by taking a spot on the Mount Rushmore of Woke alongside past champions Jemele Hill and Keith Olbermann?

That’s what we’re about to find out as the 3rd annual Woke All-Star Challenge gets down to business with 16 of the craziest & wokest voices from the world of sports media — and now the NBA coaching ranks(!) — battle it out for one of the biggest honors on the Internet.

The play-in round is complete. Max Kellerman, Jalen Rose, Gregg Popovich and Bomani Jones survived and advanced to the Sweet 16 with rather dominant performances, but now the real competition begins as each will face the No. 1 seeds. We’re talking about the titans of the woke industry.

It’s time to separate the woke pretenders from the contenders.

Let’s get to the rules:

  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. Yes, wokes are encouraged to go woke AF during the competition in order to influence his vote counts. That’s the name of the game. Woke never sleeps.
  5. The Woke Sweet 16 voting takes place Thursday, March 16; Elite 8 voting takes place Friday, March 17.
  6. Then it’s onto the Identity Politics Final Four on March 23 and March 24.
  7. The 2023 Woke All-Star Challenge winner will be announced Monday, March 27 (because we want to maximize the clicks and eyeballs and Monday morning before the national championship makes the most business sense).
  8. No purchase necessary.

There’s not much else to do here besides figure out who wants it more. Who is willing to leave it all on the line over the next two weeks. Don’t think for a second the wokes don’t know they’re playing for a title. This is one of the biggest street cred tournaments in the world.

Let’s do this.

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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  1. I get the feeling people have forgotten what Hradek did and are going with the familiar woke powerhouse Karen Rovell. I think telling someone to go volunteer for the Russo-Ukrainian war and get blown up by Western ordinance over simply not believing the globohomo narrative on the rainbow collective is an APOCALYPTIC take.

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