2025 Woke All-Star Challenge Champion - Keith Olbermann!

When the history books are written on the Era of Wokes, Keith Olbermann's smug face will be on the cover after what he accomplished in the 2025 OutKick Woke All-Star Challenge. 

The former ESPN SportsCenter great who went on to become one of the wokest hosts in the history of MSNBC, which is saying something, did the unthinkable last night when he DEMOLISHED Joy Reid, who seems to have a thing against white people, and now the United States. 

In a last-minute attempt to win the Woke Challenge, Joy Reid went on woke Don Lemon's show to announce that Canada…YES, CANADA, would beat the United States in a war. 

That will go down as one of the wokest, dumbest things ever said in the history of mass media, but IT WAS NOT ENOUGH. 

With 58% of the vote, Olbermann becomes the first two-time Challenge winner, but this victory is special because it came against three past champions and up-and-comer Sunny Hostin from The View, who is looked at as a Next Gen woke who will be a force over the next 4-5 years. 

Olbermann didn't just outlast the competition, he destroyed them. In the Final Four matchup against Hostin, Keith beat her with 65.5% of the vote. That's one of the widest margins in Identity Politics Final Four® history. 

While Joy Reid was screaming about Canada beating the U.S. in a war, Keith countered with a championship night diatribe centered around the Jackie Robinson DEI web page controversy. 

In the end, it was more than enough. 

Nobody closes in the Woke All-Star Challenge like ‘Closer’ Keith Olbermann. 

All hail the King! 

Past Woke All-Star Challenge champions: 

Jemele Hill (2021)

Keith Olbermann (2022, 2025)

Bomani Jones (2023) 

Joy Reid (2024)