The OutKick 2024 Woke All-Star Challenge

Is this Rex Chapman's year? Will ESPN's cop hater Mark Jones finally climb to the mountaintop of woke? Will race-baiting Dawn Staley use her platform to become the first female woke since Jemele Hill in 2021 to win it all? Will we see the very first literally woke, and literally dead website, Deadspin, use a fake blackface controversy to its advantage to win it all?

It's time, once again, for the wokes to put it all on the line in OutKick's 4th Annual Woke All-Star Challenge. Voting begins on Tuesday here at OutKick. 

Will newcomer Sheryl Swoopes use her Caitlin Clark comments to her advantage to come out of an all-biological female #MeToo regional to win it all? Will USA Today wokester Dan Wolken, whose name might not ring a bell for those who don't keep track of the woke world, shock the world and come all the way out of the Toxic Masculinity region? 

Folks, this is Dan's fourth year competing. He's a stud at this game. From COVID freakouts to being mad at Auburn basketball coach Bruce Pearl for supporting Senator Tim Scott, Dan Wolken is one of the most-versatile wokes in the game. This guy once claimed climate change is a major threat to college football

Let's take a look at the full bracket and the play-in matchups which have people buzzing:

How does the Woke All-Star Challenge work?

• All matchups will have a 24-hour voting period

• Play-in round voting begins March 19

• Sweet 16 voting begins March 21

• Elite 8 voting begins on March 22

• Identity Politics Final Four begins on March 28

• Woke All-Star Challenge Championship begins on March 29

• VOTE RIGHT HERE ON OUTKICK

Where are the woke greats like Keith Olbermann?

It has been the Woke All-Star Challenge committee's stance to retire past champions to make life easier for the rest of the wokes. That means Jemele Hill ('21), Keith Olbermann ('22) and Bomani Jones ('23) have been retired from competition. 

Consider them the first three faces on the OutKick Mount Rushmore of Woke. 

They're the best in the business. They're retired. 

How is Mark Cuban facing Dan Le Batard in a play-in matchup?

Since introducing the play-in round in 2022, the Woke committee has made it a priority to make the play-in round interesting for the Internet audience that demands red meat in the early rounds. As I've said, this is like the NCAA offering up UCLA-Indiana to TruTV as an 11 vs. 11 matchup in Dayton. 

Plus, with just 20 competitors, the Woke All-Star Challenge is a best of the best battle. There are no cupcakes here. There are NO 16-seeds. Even a guy like Stan Van Gundy has one helluva woke resume.  

Who's the favorite?

2024 Woke All-Star Odds & Ends

• Fans are calling Christine Brennan the head of USA Today's Axis of She-vil

• Wolken, Pat Forde, Mark Jones and Mike Florio are the only four-time competitors

• Covidbro Darren Rovell was cut from the 2024 challenge after three straight appearances; His collection of MLK memorabilia that he won't give to the MLK museum wasn't enough to get him in this year.

• This is the first year the committee has allowed woke news talking heads to enter the challenge. The original goal was to keep this amongst people tied to the sports world, but this year we're testing out Joy Reid and Don Lemon to see if they have been woke enough.

• Why is RG3 in this competition? I'll let OutKick's Bobby Burack address this one

And with that, let's sit back and enjoy everything we love about March – the brackets, the battles, the upsets, the last-second ballot box stuffing, the drama, the emotions. 

It's time once again for one of these titans to rise up to be included on the Mount Rushmore of Woke. 

Do you have Woke All-Star Challenge questions?

Email: joekinsey@gmail.com

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.