Hack Madness: Olbermann gets last laugh on Maddow, Joy Reid upsets Nikole Hannah-Jones ahead of Sweet 16

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The second round of the “Liberal Hack Tournament” was an absolute bloodbath with media stars clawing their way into the Sweet 16 of the NCAA-style contest presented by the “Ruthless” podcast. 

Things heated up in the Liberal Activists division where left-wing commentator Keith Olbermann got the last laugh against his former MSNBC colleague Rachel Maddow. 

Olbermann, who currently shouts his commentary from a Manhattan balcony, has allegedly been eyeing a return at MSNBC and was even plugging himself to take over Maddow’s time slot as she rolls back her on-air presence. Maddow herself reportedly put the kibosh on him being her successor. 

Well, as Maddow learned the hard way this week, revenge is a dish best served cold. Olbermann roasted her in a 68-32 vote, shutting Maddow out of the Sweet 16 for a second year in a row. 

Olbermann, in his tournament debut as No. 5 seed, will face a “Liberal Hack” juggernaut, Washington Post columnist and defending champion Jennifer Rubin. She obliterated CNN media reporter Oliver Darcy with over 93% of the vote. 

Can Olbermann slay the “Hack” queen? Only time will tell. 

MSNBC star Rachel Maddow shut out of the Sweet 16 once again, this time by her former colleague Keith Olbermann. 

The biggest upset of round two came between “The View” co-host Joy Behar and former Vox journalist Aaron Rupar. 

Rupar, a No. 3 seed, is famously known for sharing false and misleading tweets, so much so that his last name became an official word in the Urban Dictionary which is defined as “To lie with impunity; a brazen statement with a focus on misleading, usually with intention of a predetermined outcome.” Last year, he reached the Final Four after becoming the Way-Too-Online division champion. 

This year, he was apparently no match for Behar, a tournament rookie, who crushed Rupar with 58% of the vote.

Behar, a No. 11 seed, will next compete with another newcomer, “Late Show” host Stephen Colbert, a No. 2 seed. If she defeats him, it could pave the way for her “View” colleagues to enter the tournament next year. 

"The View" co-host Joy Behar is becoming a trailblazer for daytime TV in this year’s #HackMadness.

Sending shockwaves from the Way-Too-Online division was MSNBC’s Joy Reid taking out No. 1 seed Nikole Hannah-Jones. 

Reid, a No. 8 seed, squeaked out a narrow victory over the “1619 Project” creator in a 51-49 final. Hannah-Jones’ prolific tweets constantly racializing politics have cultivated a massive following. Even during her match Monday night against Reid, who she had been trailing behind, the New York Times Magazine reported attempted a Hail Mary with a marathon of tweets claiming that tipping waiters is racist. Unfortunately for her, she simply could not keep up with the “ReidOut” host’s impressive portfolio. 

The MSNBC star will next clash with liberal columnist Molly Jong-Fast, a No. 5 seed. But the momentum Reid has already built may already secure her spot in the Elite Eight. 

Meanwhile, Washington Post columnist Taylor Lorenz sent The Atlantic staff writer David Frum packing winning 63% of the vote. 

Lorenz, a No. 2 seed, is hoping to go further in the tournament this year after she was defeated in the Sweet 16 last year, but she will first have to overcome “How to Be an Antiracist” author Ibram X Kendi, a No. 3 seed. It will be the ultimate match between Lorenz’s iconic “internet culture” brand versus Kendi’s influential critical race theory vision. 

Washington Post columnist Taylor Lorenz is hoping to use her social media savviness to reach "Hack" glory. (Photo by Jerod Harris/Getty Images)

In the Fake News division, CNN’s left-wing media guru Brian Stelter continues his undeniable dominance, chewing out his colleague Jim Acosta by a whopping 83-17 margin. 

After squeezing out a victory in the first round, Jeffrey Toobin failed to pull it out again as he was beaten by CNN primetime anchor Don Lemon in a 64-36 final. It was a messy performance by CNN’s chief legal analyst, who ultimately couldn’t keep it up. 

Lemon, who was previously defeated in the Sweet 16 last year, has grim chances of going further this year as he will be up against heavyweight “Liberal Hack” champion, Brian Stelter.

Also still competing in the Fake News division is Lemon’s former bestie, ex-CNN anchor Chris Cuomo, who easily defeated CNN correspondent Manu Raju with nearly 75% of the vote. 

The scandalous No. 6 seed will next be competing against the No. 2 seed, The Bulwark editor-at-large Bill Kristol. This will be a closely-watched match as Cuomo’s high-profile drama will be up against Kristol’s cult following. 

CNN anchor Don Lemon fought tooth and nail against Jeffrey Toobin, who he sent zooming home this week in the "Liberal Hack Tournament."
(Theo Wargo/Getty Images)

Finally, in the Establishment division, it was a slugfest among NeverTrumpers and ex-GOP strategists. 

MSNBC contributor Matthew Dowd is lasting far longer in the “Liberal Hack Tournament” than on the campaign trail in Texas’s lieutenant governor’s race, giving Washington Post columnist Max Boot the boot with 54% support.

Dowd’s pal Nicolle Wallace wasn’t nearly as lucky, being defeated by CNN contributor Jonah Goldberg in a close battle, end with a razor-thin margin of 50.3-49.7. The “Deadline: White House” host will now be forced to return to her day job of rarely covering the Biden White House. 

Dowd and Goldberg, the No. 1 and 4 seeds respectively, will enter what is expected to be a brutal dog fight, but it is becoming increasingly certain that Dowd can secure a spot in the Final Four.  

The Lincoln Project still has a horse in the race with co-founder Rick Wilson making the disgraced anti-Trump PAC proud. Wilson eliminated “Radio Free” Tom Nichols from the competition with 54% support, earning himself an ice-cold beer from his iconic Confederate flag cooler. He will next take on CNN contributor Ana Navarro, who took out the French… as in The Dispatch senior editor David French, with over 65% of the votes.

This year’s tournament has so far collected over 250,000 Twitter votes.

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