2022 Woke All-Star Challenge Final Four – VOTE!

And then there were four white guys marching on in the 2022 Woke All-Star Challenge to the Identity Politics Final Four®. In what can only be described as a clash of woke titans, the fans will get the matchups they've been dreaming of since news dropped from the selection committee that Jemele Hill would be retired from competition.

In the world of woke, there's nothing better than four white guys in a war to prove they've put in the extra woke reps, that they've been the first woke in the building and the last one to go home after a long day of peacocking on social media.

Let's get to the matchups and gambling odds!

Identity Politics Final Four®

Rex Chapman vs. Dan Wolken

Excuse me while I catch my breath over this matchup. It's the woke version of Duke-UNC. So white. So woke. So pure. The woke gods are up in their white woke heavens looking down and nodding over the effort both of these gentlemen have given over the last year. Rex had such a big year that in September he took time out of his busy day ripping off social media content to define woke.

Meanwhile, his competitor just has that 'it' woke factor. He's what the scouts like to call a 'five-tool woke.' Dan Wolken checks all the woke boxes. From COVID, to the police, to Trump, to inequalities, to inclusion, Wolken just isn't afraid to dip his toes in the woke water.

It's a tough vote. Take your time.

Moneyline odds as set by @beatinthebookie

Chapman +250

Wolken -300

Identity Politics Final Four®

Keith Olbermann vs. Darren Rovell

Can anyone stop the craziest bastard east of the Mississippi River? Darren Rovell doesn't think so. He tweeted as much when the brackets were released and he saw a potential No. 1 battle in the Final Four. This isn't the first time these two wokes have tangled. Back in the fall, Olbermann (possibly sensing an upcoming Woke All-Star Challenge war) went after the coronabro with a heavy barrage of vitriol.

Olbermann wrote that Rovell's "blank, dazed, stupid, check-engine light look in your eyes is the full and total expression of your soul."

Woke on woke crime!

However, being the titan of the woke industry that he is, Rovell had a special weapon up his sleeve -- his MLK collection that he won't donate to a museum. That's right, Rovell claims ownership of a warden's logbook from a Birmingham jail that has 12 MLK autographs as MLK signed in and out his mail 12 times!

I'm telling you right now, Olbermann is flat out the craziest bastard of our times, but Rovell understands the woke game. He's like the utility hitter who understands his job and does it well.

Take your time. Really think about this vote.

Moneyline odds as set by @beatinthebookie

Olbermann -370

Rovell +280

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.