Crazy Keith Olbermann Wins 2022 Woke All-Star Challenge

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In the end, it really wasn’t a fair competition. The Craziest Bastard East of the Mississippi River, Keith Olbermann, was built to dominate OutKick’s Woke All-Star Challenge. With a staggering 80% of the votes, Crazy Keith is your 2022 Woke All-Star Challenge champion and figures to go the way of 2021 Woke Challenge champ Jemele Hill – instant retirement.

Folks, we officially have our first two members of the Mount Rushmore of Woke.

Olbermann, who celebrated his title by going berserk on the Washington Post for interviewing Donald Trump, woke-stomped toolbag Rex Chapman in a fight that ended up being unfair from the get-go.

Keith Olbermann Woke champion 2022
Your 2022 Woke Challenge winner – Crazy Keith / via Getty Images

Keith showed Thursday just how you win these titles and head straight into retirement.

“The [Washington Post] has given free space to Crazy Trump this morning. The millionth Crazy Trump interview is not unusual, newsworthy, nor journalism. [Josh Dawsey] wrote it and most Post types are desperately RT’ing. Shame on them, and shame on you if you reward them by reading it,” Olbermann tweeted Thursday.

It didn’t matter to Crazy Keith if Post reporter Josh Dawsey was critical of Trump in the story, our Woke Champion saw Trump and went into full triggered maniac mode. He followed up his anger at the Post with tweets claiming Trump is a pedo.

Keith Olbermann snaps Washington Post Trump interview

As Fox News pointed out, all living presidents have taken part in sit-down interviews with media outlets over the last year, including Jimmy Carter who sat down to reflect on his 75th wedding anniversary to wife Rosalyn.

Crazy Keith is just this nuts. A year ago, Keith was railing against The Masters and calling for a boycott of the golf tournament due to “Georgia voter oppression.”

THIS is how you win a woke challenge with an expanded bracket full of wokes looking to take you out in the Identity Politics Final Four.


Written by Joe Kinsey

I'm an Ohio guy, born in Dayton, who roots for Ohio State and can handle you guys destroying the Buckeyes, Urban Meyer and everything associated with Columbus.


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  1. I said it before and I’ll say it again. At some point, we’re gonna need a Woke Tournament of Champions (or Tournament of Losers). Maybe we need to do this two more years so we have four winners and then we can do it. Just sometime to keep in mind

    • Technically she’s not a sports personality so I don’t know if they would include her – but I’d certainly vote for her! In the meantime, next year’s candidates will have big shoes to fill after Keith’s runaway victory!

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