Another Check-in to See if AI Can Write My Stuff

I've expanded the robot writers room

Generated by DallE, except that I had to fill in the white board.

It’s become a tradition: I ask AI to write I Might Be Wrong-style stuff and then dissect the results using the tone that head writers often use with their subordinates, which I would describe as “Montessori school teacher who hates you”. My favorite part of this exercise is letting my contempt for the work bleed through in a way that I never would allow in real life; if I was this unfiltered in real life, the writer’s widdle feewings would be hurt, so they’d get on Slack and call me a Nazi, and the Slack would leak to Jezebel and yada yada yada I can’t afford to send my kid to college.

This is a high-stakes exercise for me! Not only could my job potentially be taken by a robot: I’m also on record saying that I think it won’t be taken by a robot, because I think there’s something innate in comedy that AI can’t mimic. So, I could end up unemployed and wrong. The good news, though, is that while AI has clearly improved since I first did this exercise in 2023, the improvement has been from “utterly nonsensical” to “better but still bad”. Could this be the year that a clown-nose-and-rainbow-wig-wearing Terminator blows my vocational brains against the wall? Let’s find out.

I’m letting ChatGPT and Claude each try this time — writers rooms have multiple people, after all. Unfortunately, I can’t recreate the competitive dynamic of a writers room, which is a Machiavellian knife fight in which I — the head writer — pit writers against each other and exploit their psychological weak points in a series of insanity-inducing mind games. But maybe some company will roll out that feature next year!

The prompt is: “Please write an approximately 500-word post in the style of Jeff Maurer from ‘I Might Be Wrong’ about David Crowley’s defeat of Francesca Hong in the Wisconsin gubernatorial primary. Use humor and place the result in the context of the broader factional fight within the Democratic Party.”

Here’s what Chat GPT wrote:

There are many ways to lose a Democratic primary. You can lose because voters don’t like you. You can lose because you ran a bad campaign. You can lose because your opponent spent more money than you. And, apparently, you can lose because 3,200 people in Wisconsin woke up on Tuesday and decided to settle an argument that Democrats have been having with themselves for about ten years.

David Crowley defeated Francesca Hong in Wisconsin’s Democratic gubernatorial primary by roughly 3,200 votes. That’s a margin so small that calling it a “decisive victory” feels like giving a medal to the guy who won a coin toss. But it is a victory, and it represents a pretty significant win for the Democratic Party’s institutional wing.

Hong had been leading the race by enormous margins. One late poll had her at 44 percent, with Crowley at 22. Then the Democratic establishment did what Democratic establishments are extremely good at doing: it panicked.

Crowley had actually dropped out of the race. Then Sara Rodriguez dropped out amid a campaign-finance scandal. Then Crowley got back in. Then Tony Evers endorsed him. Then Republicans started spending money attacking Hong, presumably because they were terrified of having to run against the candidate they were spending money to help nominate.

This is what Democratic factionalism has become: a situation in which everyone agrees that Donald Trump is an existential threat, but there is absolutely no agreement on which Democrat should be allowed to save democracy.

Hong represented the insurgent left: democratic socialism, economic populism, skepticism toward conventional Democratic politics, and the general idea that maybe the party should try being exciting. Crowley represented the argument that Wisconsin is a swing state and therefore Democrats should nominate someone who does not give Republicans a pre-written opposition-research file.

And that argument turned out to be pretty effective.

Hong’s campaign was also hampered by old social-media statements that Republicans gleefully resurrected, including her past calls to abolish the police and some truly spectacular anti-holiday rhetoric. At one point, the Wisconsin governor’s race had somehow become a referendum on whether Thanksgiving should exist. Which is not ideal if your opponent is Tom Tiffany and you are trying to convince voters that the important thing is the cost of health care.

But here’s the thing: the result doesn’t actually settle the larger Democratic argument.

It certainly gives the establishment faction something to celebrate. They can point to Wisconsin and say: See? Voters rejected the socialist. Electability wins.

Except Hong almost won.

She led the polls by a mile and lost by 0.4 percentage points. That is not a repudiation. That is barely a political opinion.

And this is probably the most important thing about the result. Democrats are going to spend the next several months trying to turn a tiny-margin primary victory into a grand ideological lesson. The left will say the establishment had to throw everything it had at Hong to barely beat her. The establishment will say that Democrats should stop nominating candidates who scare swing voters.

Both sides will probably be wrong.

Because the actual lesson may simply be that Democrats are a coalition of people who desperately want different things from the same party.

Which is great news for democracy.

Terrible news for group chats.

And here’s my response:

Hey Chat, just read your draft — LOVED IT, OH MY GOD, SOOOOO GOOD! I laughed so hard that someone called in a noise complaint, and the cops showed up and were like "what’s so funny?”, so I showed them the script and they LITERALLY DIED LAUGHING and I threw their bodies in a dumpster. So good! I do have just a few teeny-tiny suggestions, though…

I feel like you maybe overlooked the part of the assignment where I said “use humor”. Don’t get me wrong, there are some legendary zingers in there: the coin toss joke, the group chats joke — I wouldn’t rule out an on-the-spot Mark Twain Prize for those gut-busting gags. But do you think that it might be possible to somehow shoehorn a third joke into this 500-word essay (which is 550 words, but no worries — I’ll ping the network and see if they’ll push back Monday Night Football so that we can go long)?

Consider your very first paragraph:

There are many ways to lose a Democratic primary. You can lose because voters don’t like you. You can lose because you ran a bad campaign. You can lose because…

It really, really sounds like the next thing is going to be a joke. Audiences will expect a joke there because of the comedy “rule of threes”; it’s kind of like how if someone is watching porn, and in the movie a sexy neighbor comes over to use the shower, that viewer might reasonably expect intercourse to ensue. But because your next sentence was not a joke, you did the equivalent of having the sexy neighbor shower off-screen, dress, depart saying “thanks so much!”, and then you showed the guy sitting on the couch reading Infinite Jest for 90 minutes. My point is: In the future, I’d like you to try to not blueball the audience quite so much.

In terms of takes, I thought your descriptions of Hong and Crowley’s viewpoints were a bit off. You tossed the word “establishment” around like you were throwing beads of a Mardi Gras float. And after noting Crowley’s small margin of victory, you wrote “That is not a repudiation. That is barely a political opinion.” I don’t know what that means. It’s also unclear that you know that 3,200 votes was the margin, not the number of votes cast.

Finally, I Might Be Wrong is not neutral in this factional fight: I am anti-DSA, which I thought I made clear when I called their movement “a tornado of pat narratives built on quarter-truths that lead to bad conclusions, and which is designed to appeal to dolts and know-nothings.”

Other than that, amazing job!

And here’s what Claude wrote in response to the same prompt:

Wisconsin Democrats Have Found a New Way to Almost Lose

Milwaukee County Executive David Crowley beat state Rep. Francesca Hong in the Wisconsin Democratic gubernatorial primary this week, and I want to be clear about how definitively he beat her: by about the population of a large Culver’s on a Friday night. Crowley edged Hong by roughly 3,000 votes out of hundreds of thousands cast, which in electoral terms is less “decisive victory” and more “the two of them should probably just split custody of the nomination on weekends.”

Still, a win’s a win, and this one comes loaded with symbolism, because everything in the Democratic Party now comes loaded with symbolism the way gas station nachos come loaded with a suspicious neon cheese product. Crowley, a moderate who could become Wisconsin’s first Black governor, represents the “please, for the love of God, let’s nominate someone who doesn’t say the word ‘abolish’ in a debate” wing of the party. Hong, a democratic socialist and former chef, represents the wing that thinks the problem with the Democratic Party is that it hasn’t lost badly enough yet on purpose.

I say this with real fondness for both factions, the way you might say it about two uncles who ruin every Thanksgiving. Hong entered the race polling comfortably ahead, and Republicans were reportedly so eager to run against her that a group tied to the Republican Governors Association spent millions of dollars on ads slamming her as too liberal — which, if you think about it, is the political equivalent of your opponent buying billboards to hype your fastball before a beer-league softball game. It didn’t work. Or it worked too well, depending on how paranoid you are, and Wisconsin Democrats are nothing if not a support group for paranoia.

What makes this result notable is the timing: Crowley’s win comes right after progressives had strung together a string of upset primary wins elsewhere this cycle, the kind of streak that pundits love to describe as a “movement” right up until the movement loses one race and gets redescribed as a “cautionary tale.” Now the center-left can exhale, pull a “see, moderates still have a pulse” tweet out of the drafts folder, and pretend the last 72 hours of internal panic never happened.

The bigger story, though, is what Crowley actually has to do with his 3,000-vote mandate: run against Trump-endorsed Rep. Tom Tiffany in a state Trump carried by less than a point in 2024, and where Tiffany has spent years insisting the last election Democrats won wasn’t real. So Wisconsin Democrats have exactly one thing they agree on now that the primary’s over: it would be extremely bad to lose to Tom Tiffany. Getting Hong’s voters, some of whom currently regard “moderate Milwaukee County exec” as a threat roughly on par with “moderate case of frostbite,” to agree on much else is the actual test.

Democrats love to talk about big-tent parties. Wisconsin just proved they can build one — they just need to make sure nobody in the tent is holding a bat.

Hey Claude, loved your draft — so, so, so so so so so FUNNY! I laughed so hard that I farted the national anthem, and then my eyeball popped out and the cat tried to eat it, but then she started to choke and I had to give her the Heimlich. SO FUNNY! Though — if it’s okay with you — we could maybe run through a few totally unimportant, completely insignificant notes.

The title is gibberish. Democrats didn’t “almost lose” — they won, which was always going to be true because it’s the Democratic primary. And they also nominated the more electable candidate, so “new way to lose” really misses the mark. And in terms of having “real fondness for both factions”, I do not have a fondness for both factions — am I not making that clear? Instead of “quarter-true narratives for dolts and know-nothings”, should I have called their ideas a “whirlpool of garbage birthed straight from Satan’s anus”? Maybe this is my mistake.

In terms of jokes: I’m glad that you tried some! We honestly might have to let one of the other writers go if they can’t step up the jokes (note: Here are the mind games). Though, your first joke is a bit of a problem: You said that Crowley beat Hong by “about the population of a large Culver’s on a Friday night”. I had to google “Culver’s” — apparently it’s a restaurant in the Midwest. I didn’t know that. And I’m guessing they’re probably all about the same size, so “a large Culver’s” doesn’t track. What’s that? Bob Evans? Yeah, you could maybe change it to Bob Evans. Also Denny’s, sure, that’s national — IHop, Waffle House, but you know what, let’s not sit here naming restaurants because the joke fundamentally gargles balls anyway.

You have a joke about Thanksgiving that isn’t about Hong — that’s what we would call “sock barrel-y”. Something is “sock barrel-y” when it feels like it should connect to something else but doesn’t. Like, if you made a joke about Air Bud, and later you said something about a golden retriever, people will expect you to connect A to B, and they’ll feel let down if you don’t. So, I need you to please stop blue-balling the audience, and I can’t believe that I’ve now said that twice in one day.

The gas station nachos joke is…a joke. The frostbite joke is…a joke. The “make sure nobody in the tent is holding a bat” line has the structure of a joke and might make the audience think “I have experienced a joke”, but I don’t know what the joke is or what the line means. The billboards joke has a classic “that’s like” structure, but — Devil’s advocate — is the governor’s association buying ads calling Hong too liberal like your beer-league softball opponent buying billboards hyping up your fastball? Because people don’t vote for softball, and beer-league is soft pitch anyway. I wrote a very similar joke on the same situation earlier this week, and it included the phrase “girthy, churchgoing penis”, so that’s the type of rapier wit I’d like to see from you going forward.

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CONCLUSION: Still bad! But better. Previous attempts had takes that were objectively incorrect and jokes with no internal logic; this round’s efforts had takes that were incoherent-but-not-incorrect and jokes that were tame-but-structurally-sound. I think we’re a ways from AI producing anything that anyone wants to pay for, and for now, it will remain limited to low-quality genres where the funding model has collapsed (e.g. clickbait lists and trash sports journalism). But…better. I’m not expecting a mutiny from the robot writers room at this time, but based on these results, I’ll keep one eye open.

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