Liberal Hacks Compete For 2020’s Top (Or Worst?) Pundit Award

Liberal Hacks Compete For 2020’s Top (Or Worst?) Pundit Award

The other matchup that jumps out at me is the possibility of Jennifer Rubin matching up with her Washington Post teammate Max Boot with the Final Four on the line.
Jeremy Senderowicz
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This is a parody. This is not meant to reflect any beliefs or statements of ESPN or the personalities named in this parody, nor any of the actual mannerisms of such people.

Scott Van Pelt: So one of the most eagerly awaited moments of the 2020 election year has finally arrived. The selection committee revealed its brackets for the Comfortably Smug #LiberalHack tournament, sponsored as always by the private equity firm Smug Enterprises. It’s Smug Enterprises—making an impact on communities all across America.

Jay Bilas, take us through the first bracket—Liberal Activist. What jumps out at you?

Jay Bilas: The committee has set up a potential all-time matchup in the round of eight, with a 1 seed of John Harwood and a 2 seed of Jennifer Rubin. Harwood has come by his number 1 seed the old Smith Barney way—he earned it. It’s only fitting that he’s announced his transfer to the CNN conference; it’s a perfect match.

Jennifer Rubin, by contrast, joined the category of liberal activists later in her career but has overmatched so many of her contemporaries who’ve been at it for much longer. She’s a powerhouse in this category and has what it takes to make a deep run, despite her inexperience.

Seth Greenberg: Rubin drew one of the most intriguing first-round matchups in Nicole Wallace, from the MSNBC conference. We know how the selection committee gives a strong boost to liberal hacks who were formerly conservative. It even has its own nickname, the “Strange New Respect” factor.

This first-round matchup is a good example, in that Rubin and Wallace cut similar profiles—women who were formerly conservative activists. But despite Wallace having made her category switch earlier, Rubin has outclassed through one simple approach: uncompromising criticism of anything President Trump or conservatives do, regardless of whether Rubin supported it five minutes prior. She’s like a professional wrestler playing to the crowds in the Washington Post conference—and the fans love it!

Jay Williams: I expect Rubin to handle Wallace easily, but I’m concerned about her ability to make it to the round of eight. When a pundit has success doing the same thing all the time, they lose the ability to adapt. I think Rubin is vulnerable to an opponent who can have a more flexible approach.

Scott: And she may draw just that opponent in the round of 16. Rece, who is lurking there?

Rece: I don’t know how Matthew Yglesias only got a 6 seed. He may have suffered from a lack of visibility in recent years due to his habit of blocking everyone on Twitter, and the committee may have bought into the conventional wisdom that he’s past his hack prime. But I think he’s still got the skills that made him such a dangerous hack in years past. After so many years of taking heat from the socialist-leaning left for being too friendly towards markets, he just came out with a case for Bernie Sanders in 2020. If he matches up against Rubin, I expect him to confuse her easily and advance.

Scott: Jay, how do you see the rest of the bracket shaking out?

Jay Bilas: I agree that we’re going to have a Rubin-Yglesias matchup in the Sweet 16. Jake Tapper is just a bad matchup fit, especially in this bracket: he’s been too independent about things like covering the recent spate of antisemitic attacks in the New York area. There are too many more consistent liberal hacks in this bracket for him to have much of a shot.

The other matchup that jumps out at me is the possibility of Rubin matching up with her Washington Post teammate Max Boot with the Final Four on the line. That could be an epic matchup, comparable to Bernie Sanders versus Elizabeth Warren.

Jay Williams: Yes, we may have a Strange New Respect matchup in the round of eight—and from the same conference? Wow! If that matchup happens, I like Rubin’s chances: they have similar approaches but Boot admitted some weaknesses in his last book, like how he never actually understood the conservative principles he used to advocate. Rubin would never do that. What’s the first rule of success as a hack? “Never admit a mistake.” Rubin knows this, which is why she’s a number 2 seed in her first time in the liberal hack league.

Seth Greenberg: I think it’ll be tough for Boot to get past Harwood in the round of 16; Harwood is just too experienced and Boot, for all his success in his first time around the league, is still learning the ropes. I like Harwood to come out of this bracket.

Rece Davis: I’m picking Yglesias. His punditry has been subpar in the Vox era, but I think he’ll rise to the challenge of this tournament and show everyone why he was synonymous with “liberal hack” for so long.

Jay Williams: I like Rubin. Talent wins out in this league, and she has that in spades. She’s got a combo that most hacks would sell their friends for: max-effort vitriol together with complete disregard for anything she said or thought a minute before. As a hack, you can’t dwell in the past—you’ve got to move on! And no one does that better than Rubin.

Jay Bilas: And I like Max Boot to pull the upset. You can’t overestimate the value of confidence, and Boot walks into every matchup expecting to be greeted as a liberator.

The Fake News Bracket

Scott: Let’s go to the next bracket—the Fake News. Jay Williams, get us started.

Jay Williams: Wow, does this bracket have some incredible personalities in it. First, we’ve got to start with the imposing number 1 seed: Jim Acosta. The CNN conference is well-represented in this tournament, but Acosta overcame serious competition to earn his top seed. He’s worked it like crazy since the moment Trump was elected.

That performance in the press conference with Stephen Miller on immigration is one that everyone in the league has studied closely, and you’ve got to give him credit for setting the model that others follow, like the Houston Astros in baseball. If he gets out of the second round, I can’t see anyone keeping him from the Final Four.

Seth Greenberg: That’s right, Jay—the second round matchup could be one for the ages. The selection committee made an inspired choice in making Benjamin Penn the number 9 seed. His Bloomberg Law conference had always been overshadowed by its sister Bloomberg and Bloomberg View conferences, but this year the hitherto-unknown Penn put his conference on the map in a big way. He came out with an explosive story on an attorney in the Department of Labor named Leif Olsen that forced Olsen to quit, by totally misreading Facebook posts and misquoting them in requests for comment.

And the best part? In the aftermath, when everyone in the universe—including some of his competitors in this tournament—were calling on him to back down, Olsen got his job back and Bloomberg View finally had to retract the story, Penn never apologized or admitted he’d gotten anything wrong! To have that much impact on a story so wrong and to not give an inch? That is a once-in-a-generation talent. In fact, there’s a good argument he should’ve been the number 1 seed in the Fake News bracket based on that performance alone.

Scott: No one can keep up that pace for an entire year, and Penn hasn’t really been heard from since then, but his impact still reverberates. Rece, can he maintain that pace for the entire tournament?

Rece: I don’t see how. But in any one matchup, he can beat anyone if he is on his game. He could easily take down Acosta and lose to whoever is in the round of 16. That’s a recipe for a bracket that could blow up completely.

Jay Bilas: Let’s not sleep on Sahil Kapur, Penn’s first-round opponent. Kapur is a great example of the workmanlike hack who makes this league work, a steady, unflashy contributor who doesn’t get much love as a Final Four pick but is a reliable contender for the Sweet 16 every year. If Penn can’t match his earlier peak, Kapur will get past him easily. I like Kapur to raise his game in future years with his transfer to the NBC conference.

Jay Williams: What makes this bracket fascinating is the mix of personalities. Looming as a potential second-round matchup is Paul Krugman versus Joy Reid. It’s the New York Times versus MSNBC, both sending conference legends. You can’t have this tournament without Krugman.

Seth: And the fascinating thing about that potential second-round matchup is that either of them are capable of anything. And I mean anything. Whether it’s Krugman repudiating deficits after eight straight years of claiming we were in a liquidity trap or Reid blaming a hacker for writing blog posts in her name years before, their fans know that these two have no limits.

Dark Horses in this Bracket

Rece: This bracket has a number of members who may have been selected for their reputations a bit. Krugman is a living legend, but how did Brian Williams snag a number 2 seed? Since his war stories inventions, how has he shaped the discourse as compared to a number of his MSNBC teammates? I think the selection committee got this one wrong, honestly.

Jay Williams: I think there’s an intriguing potential round of 16 matchup between former BuzzFeed conference teammates Ben Smith and Andrew Kaczynski. Kaczynski is yet another CNN member; the rich just get richer. But I agree: this bracket could get very weak quickly.

Seth: I have two dark horses in this bracket. The first is Williams’ first-round opponent Oliver Darcy, yet another CNN conference representative. He had the “Strange New Respect” factor when he first entered the league, but he’s been around long enough to have learned the ropes thoroughly. Especially against a weak number 2 seed like Williams, I like Darcy’s chances to advance.

The second one is Aaron Rupar of Vox, who has really distinguished himself since joining that conference. I won’t say he’s had any one performance as spectacular as that of Benjamin Penn, but Rupar has a pretty consistent record of misleading, misrendering and misstating that just keeps exceeding expectations. Maybe this tournament will be his coming-out party.

Jay Bilas: Rupar faces Don Lemon of CNN—yes, another one—in the first round. Lemon is an experienced hack who has distinguished himself against very tough CNN competition, but I agree with Seth: I like Rupar’s chances to pull the upset.

Scott: So who do we like in the Fake News bracket?

Jay Williams: I’ve got to go with the man: Acosta.

Seth: I can’t get that Benjamin Penn performance out of my mind and I think he’ll beat Acosta. I’ll go with the Nobelist, who I think has one more run in him. It’s Paul Krugman.

Rece: I think Acosta is just too strong for this bracket.

Jay Bilas: I’m going all the way with this one: Aaron Rupar introduces himself to America and goes to the Final Four.

The Establishment Bracket

Scott: Now let’s talk about the Establishment bracket. I think everyone has some thoughts on this one.

Jay Williams: Oh yeah. The selection committee got this one wrong. Manu Raju as the number 1 seed? I know everyone was impressed when Sen. Martha McSally anointed Raju a liberal hack, but the committee took that way too seriously. I mean, if I was a conspiracy theorist I’d say Raju and McSally gamed the system.

As a Republican senator, McSally gets a bonus in the committee’s ranking of opponents, and by pulling this stunt so close to the selection, Raju got a huge bonus in the recent-performance category. Someone needs to make the members of the selection committee read their Kahaneman on recency bias. Or maybe they made the selection with an empty stomach? I mean, in the CNN murderer’s row of liberal hacks, Raju barely measures up.

Rece: I have to agree. In our proprietary metrics, Raju is one of the lowest-ranked number-1 seeds in the history of the tournament. Not only do I think Raju will lose to his fellow CNN member Anderson Cooper, it might not be close.

Jay Bilas: The other thing about this bracket is that the number 2 seed isn’t very strong either! Joe Scarborough has some of the strongest record of hackery in the tournament, thanks to his strong support of Donald Trump during the 2016 primaries. But you can only go so far on a track record. I expect his fellow MSNBC member Andrea Mitchell to beat him; we are staring down the barrel of both the number 1 and number 2 seeds going down in the first round!

Seth: And there are two other matchups where I would favor the double-digit seed over the single-digit one. The 5-12 and 4-13 matchups are famous upset magnets, and I think we’ll see two more here. Chuck Todd is ranked way too low; his opponent Tom Nichols is overrated based on the Strange New Respect factor we discussed earlier and the publicity stirred up by the new Bulwark conference this year.

Todd has been climbing the ranks in the NBC powerhouse for many years and has both the skills to handle the establishment and the flexibility to maintain credibility with the online left. He’s a killer.

In the second matchup, Matthew Dowd suffers from the same visibility problem as Matthew Yglesias by blocking everyone on Twitter, but without Yglesias’ flexibility. Any benefit from the Strange New Respect factor wore off a long time ago, and his approach is particularly vulnerable to female opponents.

And he has the bad luck to draw a matchup against one of the best, Rachel Maddow of MSNBC. She gets underrated because of her knack for starting slowly, but she approaches everything like it’s the end of the republic. No one can match her intensity, even on plays that seem completely meaningless. I expect Maddow to handle Dowd easily, setting up an amazing NBC-MSNBC showdown in the second round.

The Bulwark Is Well-Represented

Scott: Aside from Tom Nichols, the upstart Bulwark conference is well-represented here with Bill Kristol as the number 4 seed and George Conway as the number 9. Do any of them have a chance to make a run?

Rece: I don’t think so. I do think Kristol can get out of the first round because of his opponent Chris Matthews, who may be one of the weakest candidates chosen by the committee from the NBC-MSNBC alliance. But while he has shown impressive hack skills in his first year in the league, he has a way to go before he can be mentioned in the same conversation as, say, Jennifer Rubin. I think his inexperience will be exposed once he faces more seasoned competition.

Jay Williams: George Conway has the misfortune to draw Jane Mayer in the first round. She should have been seeded much higher. She has such a long record of successful hackery, going back to her co-authored book on Clarence Thomas and her later work on the Koch brothers, before capping it off with her crowning achievement in pushing the Deborah Ramirez story during the Brett Kavanaugh hearings.

What do we see from her record? Two things: First, she knows how to satisfy her fan base, which is a tough crowd! It fancies itself more sophisticated and harder-to-please than the plebes who cheer on, say, Donald Trump. Not a lot of contestants in this tournament could win that crowd over the way Mayer does. Second, she believes in good teamwork, as shown by her collaborations with Jill Abramson and Ronan Farrow. That’s a tough combination for any opponent to overcome. I like Jane Mayer to come out of this bracket.

Scott: What about Michael Barbaro, of the New York Times conference? He’s a huge fan favorite but was only seeded number 14 by the committee. Will his fans have anything to celebrate?

Rece: I don’t see it. Yes, he’s from a major conference and is the biggest fan favorite in the field, but the committee got this one right. They recognized that his strength-of-schedule was very low and is likely to run into trouble playing away from his adoring fans. The tough guy Chris Cuomo will handle him easily. I know, another CNN member, but I think he’s coming out of this bracket and finally getting out of his brother’s shadow.

Seth: We are getting a double-digit seed in the Final Four from this bracket. I think it’ll be Chuck Todd.

Jay Bilas: I agree with Rece about the powerhouse Maddow-Todd matchup in the second round. I think Maddow wins it and coasts to the Final Four from there.

The Way Too Online Pundits

Scott: And now we turn to the final bracket, the Way Too Online one. And I think we all agree that the number 1 seed casts a huge shadow over this bracket. The question on everyone’s mind: can anyone take down the heavy favorite, Brian Stelter of CNN?

Seth: It will be very, very tough. Stelter is at the top of his hackery game and he’s playing it at a level as high as this league has seen in years. He didn’t earn the nickname of “the media’s janitor” for nothing. He faced down a tough opponent recently in the story of ABC killed its expose on Jeffrey Epstein and brushed it aside like it was nothing, while mowing down the story of Sean Spicer on “Dancing With the Stars” like it was a local story in the pre-Internet days. He will be a heavy favorite against any opponent.

Jay Williams: There are some other serious talents in this bracket. The 8-9 matchup between Carlos Maza and Judd Legum has the makings of a classic; put them in another bracket and either of them would be a threat to make a deep run.

And I think Ian Millhiser is another representative of the Vox conference who is seeded way too low. Both he and Rupar have really changed the look of Vox since they transferred in; the conference has achieved a whole new level of hackery thanks to those two.

But that’s not all: Millhiser’s opponent Dave Weigel could also be seeded higher. Ask anyone in the league and they’ll tell you that Weigel is one of the most respected hacks around. And when he’s feeding off the approval of his peers, he can go on a run that few hacks can keep up with. Just look at his record carrying water for the leftiest elements of the Democrats, especially the “Squad;” not everyone earns the nickname the “Roman Aqueduct.” That is a tough first-round matchup, but I think Millhiser’s creativity will enable him to pull off the upset; at any given time, Millhiser will come up with a play that his opponent never even thought was possible.

Jay Bilas: There are another two first-round matchups I’d keep an eye on. The 4-13 matchup between Chris Cillizza and Susan Hennessey is another one where the seedings maybe should be flipped. I think Cillizza’s ranking is too high from playing in the powerhouse CNN conference, while I’m shocked that Hennessey is the only representative of the Lawfare conference.

For the impact that conference had on Russia-gate and how it was covered, you’d think the committee would pick more than one of its members. Hennessey comes to play and is one of the most determined parties in the entire tournament. She never lets setbacks get her down. Another contestant might have been discouraged when the Russia collusion story turned out to have been wrong all along, but she just keeps keeping on. I don’t know how far she’ll go in this tournament, but if they had an award for determination, she’d be a heavy favorite.

My other key matchup is between Molly Jong-Fast of the Bulwark conference and Kevin Kruse, who received an at large-bid from a university in New Jersey. Don’t let the seeding discrepancy fool you: these two are very evenly matched in knowledge of all subject matters, eloquence, and how they handle opponents. I like Jong-Fast’s chances in the first round because Kruse can get too reliant on the “Well, actually” play, but it could be one of the best matchups of the tournament.

Rece: We talked about Benjamin Penn earlier. This bracket has someone who represents a plausible career path for Penn: Shaun King. I like King’s chances to get out of the first round; he’ll be a tough opponent because of his penchant for trick plays. It’s a tactic that usually has diminishing returns, especially against more experienced opponents, but I think King can get at least one victory out of it.

I would also keep an eye on the bottom of this bracket, which is surprisingly weak: the number 2 seed Laurence Tribe was a big surprise on the part of the selection committee. I think the committee fell victim to recency bias again by overweighting his recent victory over House Speaker Nancy Pelosi in the question of when to send the impeachment articles to the Senate.

Parker Molloy is, in my opinion, a lesser candidate from the Media Matters for America conference: she doesn’t usually perform well when she’s not playing to supportive crowds. In the next segment I’ll let you know who I think the committee should have chosen instead.

The Daily Beast Entrants

Scott: We should mention one heartwarming story that plays out in both this bracket and the Fake News one: Asawin Suebsang and Lachlan Markay, both of the Daily Beast conference, both earned berths in the tournament. Jay Williams, how great is that?

Jay Williams: This is what the tournament is all about, people plugging away, working hard and finally getting the call from the committee that makes their dream come true. In this case, both Suebsang and Markay aren’t just teammates, but co-authors. So the committee decided it couldn’t pick between them and found room for both. You’ve got to appreciate that.

Rece: And especially for Markay, this is his first time around the league after transferring into it. It’s tremendous validation for his efforts to be picked for this tournament.

Jay Bilas: Unfortunately, they both drew number 16 seeds against very tough opponents: Markay goes up against John Harwood over in Liberal Activist, and Suebsang has the impossible task of trying to defeat Stelter. It’s a wonderful story, but the clock is about to strike midnight and the Cinderella ride is over.

Scott: So we’re talking around the question: can anyone beat Stelter?

Jay Williams: Not in this bracket.

Seth: Nope.

Rece: This bracket was made for a Stelter coronation.

Jay Bilas: It’s unanimous.

The Snubs

Scott: So CNN may have a lot of entrants in this tournament—in fact, if we could Harwood with his pending transfer, they have all four number 1 seeds! But we’ll have to see if they live up to those expectations. Now let’s get to the most fun portion of the program: the snubs. Who has a beef with the committee?

Seth: There is one obvious choice here, for which there is a reasonable explanation but it still stings. Brian Beutler deserves to be in this tournament. From a record of strongly supporting Trump in the 2016 primaries to excoriating any conservative who has, at any time, either expressed any skepticism of Trump or any support of him, Beutler has compiled an unbroken record of bad faith, hypocrisy, and nastiness. Those are exactly the traits the selection committee is looking for in picking contestants for this tournament.

So why didn’t he make the cut? Unfortunately, he’s just in the wrong conference. The Pod Save America conference, while very influential, falls into the category of Obama administration alumni, who are excluded from this tournament because the committee feared there’d be no room for anyone else. I hope the committee changes the rules for next year: Beutler was the one hardest hit, but a tournament meant to feature the best liberal hacks shouldn’t exclude hacks of the caliber of Jon Favreau, Dan Pfeiffer, and Tommy Vietor either.

Jay Bilas: The New York Times conference was underrepresented this year, and I was surprised Jamelle Bouie didn’t make the cut. The selection committee clearly was sending a message that a Twitter feed equally divided between spurious accusations of racism and denials of doing any such thing isn’t enough any longer: the bar has been raised. I expect Bouie to come back strong and earn a high seed next year.

Rece: I mentioned earlier that the selection committee should have chosen someone else for Parker Molloy’s slot—I’m talking about Ashley Feinberg from the mid-major Slate conference. Both she and Molloy have well-developed social media mob-incitement games, but Feinberg isn’t afraid to go up against the biggest opponents and is feared around the league for her sleuthing skills. The committee whiffed on this one, I’m sorry to say.

Jay Williams: I was surprised that David Frum didn’t make the cut. Atlantic conference commissioner Jeffrey Goldberg must be really disappointed at not making a better showing this year; they’ve tried to maximize their ranking for this tournament ever since they forced Kevin Williamson to transfer out of the league.

It’s one thing for traditional powerhouses like the New York Times and the Washington Post to be underrepresented in the brackets; they’ve never tried to appeal overtly to the committee and it shows. But for a conference to rejigger with so much publicity in order to appeal to the committee and then get shut out? That’s rough.

Scott: It seems like Frum and Tom Nichols were playing for one slot and Nichols won out this year. The committee has always highly valued a reputation for expertise.

Jay Bilas: I was also surprised that Josh Marshall didn’t make the cut. He is such an influential figure in this league that it seems wrong to have this tournament without him. It’s not just that he was a pioneer of so many of the plays used by everyone in this league, but the Talking Points Memo conference he founded has served as a feeder for so many more established conferences. The league is full of his disciples.

Rece: Just like I’m saying with Ashley Feinberg—Gawker alumni are underrepresented in this tournament, but that conference’s influence lives on.

Scott: That’s the perfect note on which to end this program and segue to our next one. Thank you so much for joining us. Don’t forget to come back on Wednesday, when we are joined in studio by former President Barack Obama to unveil his picks.

Coming up next, the world premiere of a special 30 for 30 documentary on a conference which was legendary for so long but has fallen so low that it’s not even news when they fail to place anyone in the tournament. How did a conference that influenced so many for so long, whose alumni dominated the league for decades, fall on such hard times? It’s “TRB: The Rise and Fall of The New Republic,” produced and directed by Billy Ray, starting…now.

Jeremy Senderowicz is a New York City lawyer who is very disappointed the Yankees didn't dominate baseball further after the advent of free agency. Follow him on Twitter at @jsende.

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