2022 Woke All-Star Challenge Championship – Vote!

It has come down to this: Chapman-Olbermann. One of these privileged white men will ascend to the Mount Rushmore of Woke and join Jemele Hill as a champion of the woke community -- and likely head off into retirement because these two destroyed opponents on the way to the finals of the 2022 Woke All-Star Challenge.

The Craziest Bastard East of the Mississippi, also known as Keith Olbermann, absolutely destroyed Darren Rovell and his MLK autograph collection in the Final Four with Olbermann garnering an astounding 88% of the vote. Chapman was nearly as dominant against the hated Dan Wolken who should one day find himself on the Mount Rushmore of Woke.

But it's going to take time because there are two titans of the industry in front of him and these two are set for a battle for the ages.

Identity Politics Woke All-Star Challenge Championship match

Rex Chapman vs. Keith Olbermann

Former ESPN hero Olbermann rolls into the finals after spending his weekend fighting his typical political battles and reminding people why he was the odds-on-favorite to join Jemele in the woke HOF.

But, if there's anyone with the ability to derail the runaway train that is Olbermann, it's Rex Chapman and his stupid glasses. Rex, who is now sucking up the CNN+ money before that channel goes belly up, has sorta gone corporate with his social media offerings, but he still has that 'it' factor that led him to the complete destruction of Wolken.

Now it comes down to one final vote. This one is for all the woke marbles. Stop and think real hard here. Olbermann will be retired like a pair of mowing shoes if he wins this battle. That means you'll be left with another year of Rex Chapman in 2023. Is that what you really want?

Step up and make the call.

Moneyline odds as set by @beatinthebookie

-300 Keith

+240 Rex

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.