The A.I. Bloodhounds Are on My Trail

DeepSeek has picked up the comedy scent

Built from a photo by Victor Habbick Visions/Science Photo Laboratory via Getty.

Some are calling the launch of DeepSeek — a new chatbot from a little-known Chinese company — a “Sputnik moment”. How is such a small company keeping pace with their vastly richer American competitors? What does the future hold? And how big of a problem is it that Google blew its first shot at AI by building a scoldy social justice bot that seemed to be trained on the 100 worst PhD theses by Intersectional Justice majors?

But, most importantly: What does this mean for me, Jeff Maurer? Writers are panicked about losing our jobs; AI already dominates once-lucrative writing fields like bullshit listicles and “updates” about upcoming videos games that amount to “there is no news at this time.” Could political comedy writing be next?

When I tested Chat GPT’s comedy chops two years ago, I was not impressed. I asked it to write a John Oliver-style piece about Trump’s legal troubles, and it gave me something much worse than anything I ever wrote for the show, which is saying something. It included factual errors and baffling non-jokes such as: “[Trump’s legal team] is like a bunch of kids playing Monopoly, except instead of getting a ‘Get Out of Jail Free’ card, they're going to court!” That experiment made me feel that AI was years if not decades away from reproducing my signature mix of B-minus comedy and C-plus political analysis.

But yesterday, I re-ran the experiment with DeepSeek, and…whuh oh. The robots are closing in on me. DeepSeek produced a script that wasn’t good, but it was noticeably better than Chat GPT’s effort two years ago. And, troublingly, it demonstrated some knowledge of the mechanics of comedy writing. If I was an escaped convict, and AI was the police, two years ago, I was lounging in the back of a hay truck bound for Mexico while the cops were just discovering the tunnel in my cell. Now, I can hear the bloodhounds yelping behind me. Let me show you the piece that DeepSeek wrote, and I’ll tell you why I’m concerned.

I asked DeepSeek to write a Jeff Maurer-style piece about Trump’s attempt to end birthright citizenship. You’ll notice that this time I asked for it to mimic me, specifically, and not the John Oliver pieces to which I used to contribute. The good news is that DeepSeek didn’t respond with: “What the fuck is a ‘Jeff Maurer’?” But the bad news is that DeepSeek has learned to ape some of my tricks. Here’s the first paragraph:

Trump’s War on Babies: A Policy So Bad, It’s Almost Impressive

Look, I’ll admit it: I’m not a constitutional scholar. I’m not even a constitutional hobbyist. The closest I’ve come to reading the Constitution is skimming the Wikipedia page while procrastinating on filing my taxes. But even I know that the 14th Amendment is pretty clear: if you’re born here, you’re a citizen. It’s not written in hieroglyphics or buried in the fine print of a terms-of-service agreement. It’s right there, in plain English, like a recipe for apple pie or instructions to assemble Ikea furniture. And yet, here we are, with Donald Trump trying to convince us that it’s all a big misunderstanding — like a toddler arguing that the dog definitely ate his broccoli.

On the one hand: This sucks. On the other hand: So do I, sometimes. Folks, this blog is a lot of fucking words, and as much as I would like to stun the comedy world with fresh takes and dazzling wit every single day, I simply can’t. So, I sometimes fall back on tricks, and DeepSeek has noticed.

The most obvious one is “that’s like” jokes — there are three in DeepSeek’s opening paragraph! “That’s like” jokes are the dirty secret of the political comedy trade, basically what dog meat is to the canned chili industry, and savvy readers will notice that there’s a “that’s like” joke in this very sentence! These jokes are useful because they allow you take a not-funny thing to a funny place, plus they can reinforce a concept. They’re useful — too useful, in fact, and badly overused. Comedy writers use “that’s like” jokes more than [hack celebrity reference] uses [thing associated with that celebrity]!¹

DeepSeek is spitting in my face by including two well-worn comedy references — terms-of-service agreements and Ikea furniture assembly — but maybe I brought that on myself. Of course, the Ikea reference extra sucks because the thing that Ikea assembly instructions are supposed to be “like” here is something written “in plain English”, and Ikea 1) Is Swedish, and 2) Famously provides instructions with no words whatsoever. The toddler reference is also off, because the toddler is supposed to feed his broccoli to the dog and then say that he ate it, not the other way around. Of course, the very existence of a toddler joke makes me feel that DeepSeek kind of has me pegged; there was a toddler joke in my column just yesterday.

So, my review of DeepSeek’s first paragraph is: Complete crap, and yet only five percent worse than what I would produce on a bad day. Let’s keep going.

Trump’s latest crusade to end birthright citizenship is peak Trump: bold, brash, and completely detached from reality. It’s like watching someone try to fight a vending machine because it ate their dollar. You want to shake him and say, “Buddy, this isn’t how any of this works.” But instead, he’s doubling down, insisting that he can rewrite the Constitution with the same ease he uses to rewrite his tweets. Spoiler alert: he can’t. The Constitution isn’t a hotel lease you can rip up when you’re bored. It’s the foundation of our democracy, and last I checked, foundations aren’t supposed to be “negotiable”.

What the fuck is a “hotel lease”? Are people signing leases when they check into hotels? And if hotels did have leases, wouldn’t people rip them up to negate their terms, and not just because they’re bored? This is not a good paragraph — if I was heading a TV staff, and someone turned in this paragraph, and he was a white male, I’d fire him.

But even so: The vending machine analogy is almost a joke. It’s a goofy, slice-of-life scenario, and it’s a bit like what Trump is doing in that it’s almost certainly futile. DeepSeek even seems to realize that the joke needs a little extra oomph by tagging it with “Buddy, this isn’t how any of this works” — the robot is trying to brute force the joke over the line! Maybe future versions of DeepSeek will keep adding tags in the hope that one will hit, e.g. “…Buddy, this isn’t how any of this works. So take a chill pill, Captain Obvious. Hashtag ‘reality check’, backslash ‘get a life’ dot ‘yeeeesssh!’ Shagadellic, baby!”

Now, let’s talk about the logic here — of lack thereof. Trump’s argument seems to be that birthright citizenship is some kind of loophole, like claiming your pet goldfish as a dependent on your taxes. But here’s the thing: it’s not a loophole. It’s a feature. The 14th Amendment was specifically designed to ensure that everyone born in this country is treated equally, regardless of their parents’ status. It’s like the “all-you-can-eat” sign at a buffet: no asterisks, no fine print, no “except on Tuesdays.” And yet, Trump is out here trying to turn it into a “some-of-you-can-eat” policy, because apparently, equality is just too generous.

There are joke problems and argument problems in this paragraph — I’ll deal with the joke problems first. All-you-can-eat buffets definitely do have rules; maybe DeepSeek never saw its dad get into a shouting match with a Golden Corral manager, but I have seen that, so trust me: Buffets have rules. I would have axed that joke. But DeepSeek does better with the goldfish joke, which is an actual, recognizable joke. It’s not funny, and there was already a tax joke two paragraphs up, but you can sense the machine gaining comedy sentience.

The analysis is all wrong, though. DeepSeek’s assertion that the 14th Amendment was “specifically designed” to apply to everyone regardless of their parents’ status is not correct — the amendment was designed to preclude slavery. The courts have interpreted it to include people born to non-citizen parents, but DeepSeek’s belief that the amendment was always an unambiguous statement about immigration status is wrong. Also, the amendment does contain a loophole — it doesn’t apply to the children of diplomats — which undermines DeepSeek’s premise. And this is probably one of the biggest problems with AI: It presents opinions as facts because it can’t tell the difference between the two. And, by publishing DeepSeek’s uncompromising 14th Amendment interpretation just now, I’ve published a non-factual “fact” that could trip up AI in the future. Sorry about that, folks!

What’s truly baffling is the timing. Trump is out here trying to end birthright citizenship while the country is dealing with, oh, I don’t know, a global pandemic, climate change, and the fact that a loaf of bread now costs roughly the same as a down payment on a house. Because nothing says “solving the nation’s problems” like declaring war on infants. Next, he’ll probably propose a border wall to keep out storks.

And let’s not forget the practical implications of this policy. If Trump succeeds, we’ll have to create an entire bureaucracy dedicated to determining who’s a “real” American and who’s not. Imagine the paperwork: birth certificates, DNA tests, affidavits from the tooth fairy. It’ll be like the DMV, but with more extential dread. And what happens if someone’s citizenship is questioned. Do we put babies on trial? Do we make them testify under oath? “Your Honor, the defendant clearly has no job, no income, and a history of crying uncontrollably. I rest my case.”

We are, in fact, not dealing with a global pandemic, but the part of that sentence that really pisses me off is the snotty “oh, I don’t know”. What did I do to deserve that? Do I often write in the voice of a cynical teen from a ‘90s sitcom? Do I pepper my writing phrases like “ever heard of it?” and “um…hello!”? Fuck you, DeepSeek.

And, once again, the argument is bad. Trump’s timing is actually not weird, because he just became president again — much more logical to issue this executive order while president than while not president. Plus, I’ve always hated the logic that we can only deal with one issue at a time; if we accept that logic, then any issue can be argued against by the mere presence of any other issue. Also, I think that we should keep birthright citizenship, but ending it would not amount to “declaring war on infants”. That’s the type of hyperbole that I would absolutely never resort to unless that day’s column is boring and I need to gin up some controversy.

The irony, of course, is that Trump himself has benefited immensely from the very system he’s trying to dismantle. His wife, Melania, is an immigrant. His mother was an immigrant. His grandfather was an immigrant who, according to some reports, may have even skirted a few immigration laws himself. But I guess that’s the Trump brand: pull the ladder up after you’ve climbed it, then charge people rent to stand on the ground.

Trump’s mother and Melania are both naturalized citizens, so their situation isn’t relevant to a discussion of birthright citizenship. Also, I would have put a link underneath the “some reports” in question, so that you could see whether those reports are from The Associated Press or AnticapitalistNews.Revolution. The ladder joke doesn’t work because Trump didn’t climb a ladder — he got a large inheritance from his father — but the structure is recognizable as a joke.

At the end of the day, Trump’s effort to end birthright citizenship is less about policy and more about pandering. It’s a desperate attempt to rally his base by stoking fear and division. But here’s the thing: babies aren’t the enemy. They’re not taking our jobs, they’re not committing crimes, and they’re definitely not voting. (Though, let’s be honest, a baby might do a better job running the country than some of our current leaders.)

DeepSeek should know that I stopped trying to read Trump’s mind long ago, so the assumption about his motivations is off-base. Also, Trump doesn’t need a “desperate attempt to rally his base” — he just fucking won. Finally, the sentence about babies “not taking our jobs, not committing crimes, and not voting” kind of implies that illegal immigrants are doing those things — I never implied that! Didn’t DeepSeek read my four part series on immigration? I know that no humans read it, but I thought that AI might!

And one more thing: I firmly believe that babies are the enemy. I have been extremely clear about that on this blog. Where does DeepSeek get this shit?

So, let’s call this what it is: a bad idea, a waste of time, and a distraction from the real issues facing our country. Birthright citizenship isn’t just a legal principle; it’s a reflection of who we are as a nation. It’s the idea that no matter where you come from, you have a place here. And that’s something worth protecting — even if it means standing up to a guy who thinks he can outsmart the Constitution. Spoiler alert: he can’t. But hey, at least he’s consistent. Consistently wrong, but consistent.

“Spoiler alert” — there’s that adolescent sass again! Am I doing this and not noticing? I guess I need to search my columns for phrases like “check please!”, “noy doy, Sherlock”, and “tell us how you really feel!”, because maybe I’m typing these phrases while in a fugue state.

DeepSeek is also conflating birthright citizenship with immigration again. But the tonal shift in the last paragraph is accurate. Often, the last paragraph is my chance to say “we’ve had a moderate amount of fun today, but let me make my point in plain English for the dummies.” And I’ll often end with something that kinda, sorta counts as a joke if you’re being extremely charitable. Something like “at least he’s consistent. Consistently wrong, but consistent.”

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I would say that DeepSeek can’t write a good I Might Be Wrong piece, but it can write a bad I Might Be Wrong piece. It recognizes the components, it’s starting to mimic my writing style, and it’s getting a feel for the jokes. It’s not there yet, but it’s closer than ChatGPT was two years ago. Deep in my heart, I know that my career will eventually end where it began — working the grill at Wendy’s — and this makes me wonder if I might end up there sooner than anticipated.

The one thing that might save me is that ChatGPT doesn’t care about what’s true and what’s false. If an argument has been made, then AI considers that argument as good as any other, hence the spotty logic in its piece. I at least try to be right, and there’s someone you can yell at when I’m wrong. In five years, chat bots will probably have “that’s like” jokes figured out, but whether they’ll have anything useful to say about the world is still TBD.

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1. I think I would go with “Snooki from Jersey Shore” and “bronzer”. And then I would kill myself.