Jeffrey Toobin handily beats Jeff Zucker, Chris Cuomo sends Jimmy Kimmel packing in round one of #HackMadness

The first round of the “Liberal Hack Tournament” was a battle royale of media titans that separated the strong from the weak.

The NCAA-style contest presented by the “Ruthless” podcast had a combined total of 158,887 Twitter votes cast. And in the Fake News division, CNN stars fought ferociously, many offering early signs of tournament domination.

Brian Stelter, CNN’s left-wing media guru and the first-ever champion of #HackMadness, obliterated Washington Post columnist Greg Sargent, earning a whopping 97.5% in a blowout match.

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The “Reliable Sources” host, a No. 1 seed, will next face colleague Jim Acosta, a No. 8 seed, who despite having been sidelined this past year as CNN’s poorly-watched weekend anchor following his starring role as a combative White House correspondent in the Trump era crushed NBC News reporter Sahil Kapur collecting 91% of the vote. 

But barring divine intervention, Stelter will eat Acosta’s lunch in round two. 

Brian Stelter, the first winner of the "Liberal Hack Tournament," remains a heavy favorite in the 2022 bracket.

Brian Stelter, the first winner of the "Liberal Hack Tournament," remains a heavy favorite in the 2022 bracket.
(Kevin Mazur/Getty Images for CNN)

The biggest upset in the Fake News division came from the battle of the Jeffs: Jeff Zucker and Jeffrey Toobin

Zucker, a No. 4 seed, was forced out of the network for failing to disclose a consensual relationship with a colleague and reportedly aided disgraced Democratic New York Gov. Andrew Cuomo in the early months of the pandemic. Based on the turbulent developments plaguing CNN, Zucker was expected to go far in his tournament debut. 

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Surprising fans across Twitter, it was Toobin who came ahead of Zucker, handily beating his former boss as a No. 13 seed with 61% support. 

Toobin will next face off against Don Lemon, who crushed Politico editor Sam Stein with nearly 90% of the vote. While the CNN primetime anchor is the favorite, spectators should not underestimate Toobin’s ability to pull it out in the end. 

CNN chief legal analyst Jeffrey Toobin pulled out a victory against his ex-boss Jeff Zucker and will advance to Round Two of the "Liberal Hack Tournament."

CNN chief legal analyst Jeffrey Toobin pulled out a victory against his ex-boss Jeff Zucker and will advance to Round Two of the "Liberal Hack Tournament."
(Getty Images/Photo illustration)

The closest matchup of the division was between former CNN anchor Chris Cuomo and late-night host jimmy-kimmel” target=”_blank”>Jimmy Kimmel< he launched against CNN this week following his dramatic exit in December was no doubt a factor in his victory. He is expected to eliminate CNN correspondent Manu Raju in the next round.

Also advancing in the Fake News division are CNN editor-at-large Chris Cillizza and The Bulwark editor-at-large Bill Kristol, who will face each other in what will likely be a fierce clash. 

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Over in the Establishment division, MSNBC contributor and No. 1 seed Matthew Dowd sent Lincoln Project co-founder Reed Galen packing winning over 90% of the vote and will compete in the next round against Washington Post columnist Max Boot, who defeated Lincoln Project co-founder Steve Schmidt. 

While the Lincoln Project had a poor showing in round one, the disgraced anti-Trump PAC is still hoping co-founder Rick Wilson can carry the torch to the championship. Wilson smoked ABC News correspondent Jonathan Karl with nearly 92% of the vote and will next compete against “Radio Free” Tom Nichols. 

Others moving on to round two in the Establishment division are MSNBC anchor Nicolle Wallace, CNN contributor Ana Navarro as well as The Dispatch senior editor David French. 

MSNBC contributor Matthew Dowd burned out quickly in the Texas lieutenant gubernatorial race but still has hope in #HackMadness.

MSNBC contributor Matthew Dowd burned out quickly in the Texas lieutenant gubernatorial race but still has hope in #HackMadness.
(Lorenzo Bevilaqua)

Over in the Liberal Activists division, Washington Post columnist Jennifer Rubin trounced Daily Beast columnist Wajahat Ali by a roughly 87-13 margin. 

Rubin has reached all-star status as the defending champion and a championship finalist the year prior, proving #HackMadness is not just a man’s sport.

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Suffering a devastating blow was Rubin’s colleague, Washington Post fact-checker Glenn Kessler. While he can easily dish out Pinocchios, he has not won a single match in his entire “Liberal Hack Tournament” career. Kessler was overtaken by CNN media reporter Oliver Darcy in a nail-biter match-up resulting in a narrow 52-48 vote. 

Darcy, widely seen as Stelter’s sidekick, will likely see his dreams of “Hack” glory shattered as he is set to compete against Rubin in Round Two. 

Coming out of retirement and pulling a Tom Brady is Keith Olbermann, who cleaned the clock of his former MSNBC colleague joe-scarborough” target=”_blank”>Joe Scarborough<

Olbermann, a No. 5 seed, has taken Twitter by storm with his red-hot world-regions takes and his reported efforts to regain his stature as an MSNBC star. He may very well get his revenge in round two against Rachel Maddow, the No. 4 seed, who reportedly quashed discussions of him taking over her time slot as she rolls back her on-air presence. 

It will be quite the cage match ahead of the Sweet 16. 

MSNBC star Rachel Maddow and her former colleague Keith Olbermann will face off in a brutal cage match during Round Two of the "Liberal Hack Tournament." 

MSNBC star Rachel Maddow and her former colleague Keith Olbermann will face off in a brutal cage match during Round Two of the "Liberal Hack Tournament." 

Making strong tournament debuts are the-view” target=”_blank”>”The View”< and “Late Show” host stephen-colbert” target=”_blank”>Stephen Colbert<

Finally, in the Way-Too-Online division, “1619 Project” mastermind Nikole Hannah-Jones torched her former New York Times colleague Ben Smith with a whopping 94% of the vote. 

Hannah-Jones began her “Liberal Hack” career as a No. 6 seed in last year’s Liberal Activists division and managed to reach the Sweet 16 only to be defeated by Jennifer Rubin. Kicking off the tournament as a No. 1 seed in a new division, the outspoken New York Times Magazine reporter has a much stronger chance of going even further, but one powerhouse competitor may cut her journey short in round two: MSNBC host Joy Reid

MSNBC host Joy Reid takes on competitors in the Way-Too-Online division of the "Liberal Hack Tournament." (Evan Agostini/Invision/AP, File)

MSNBC host Joy Reid takes on competitors in the Way-Too-Online division of the "Liberal Hack Tournament." (Evan Agostini/Invision/AP, File)

The “ReidOut” host defeated her NBC colleague Yamiche Alcindor by a 77-23 margin. Alcindor, once a rising “Hack” star who reached the Sweet 16 last year, has largely been absent in the Biden era, besides when she gushed directly to the president as a “moral, decent man” during his first press conference in March 2021. But Reid, who reached the Elite Eight last year, has managed to maintain her status in the media landscape coming up with new and inventive ways to attack conservatives as racists.  

Reid may be a No. 8 seed, but her upcoming brawl with Hannah-Jones could get ugly. Don’t count her out just yet. 

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Washington Post columnist Taylor Lorenz, who was licking her wounds following her stunning defeat last year in the Sweet 16 despite having been a No. 1 seed, returned as a No. 2 seed and wiped the floor against MSNBC host Chris Hayes by a 66-34 margin. She has a much clearer path to potentially make it into the Final Four, particularly if she continues her public spat with former New York Times colleague Maggie Haberman. She will face off in round two against The Atlantic staff writer David Frum, a No. 7 seed, who she is expected to defeat. 

But a potential threat to Lorenz going forward in the Way-Too-Online division is “How to Be an Antiracist” author Ibram X Kendi, a No. 3 seed, whose writings have been famously tied to the critical race theory ideology that’s been at the center of a fierce national debate. Kendi will next be going toe-to-toe with anti-Trump Harvard Law professor Laurence Tribe. And if he wins, he could take on Lorenz in the Sweet 16. 

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