I’ve talked on Techdirt about just a few of my AI-related experiments over the past few years, including how I use it to help me edit pieces, which I still write myself. I still have no intention of letting AI write for me, but as the underlying technology has continued to level up, every so often I’ll run a test to see if it could write a better Techdirt post than I can. I don’t think it’s there (and I’m still not convinced it will ever get there), but I figured I can share the process with you, and let you be the judge.

I wanted to pick a fairly straightforward article, rather than a more complex one, just to see how well it works. In this case, I figured I’d try it with the story I published last week about Judge Boasberg ruling against the Trump administration and calling out how the DOJ barely participated in the case, and effectively told him to “pound sand” (a quote directly from the judge).

I know that just telling it to write a Techdirt article by itself will lead to pretty bland “meh” content. So before I even get to the prompt, there are some steps I need to include. First, over time I continue to adjust the underlying “system prompt” I use for editing my pieces. I won’t post the entire system prompt here as it’s not that interesting, but I do use it to make it clear its job is to help me be a better writer, not to be a sycophant, not to try to change things just for the sake of change, and to suggest things that will most help the reader.

I also have a few notes in it about avoiding recommending certain “AI-style” cliches like “it’s not this, it’s that.” Also, a specific one for me: “don’t suggest changing ‘fucked up’ to ‘messed up.’” It does that a lot for my writing.

But that’s not all. I also feed in Techdirt samples, which are a collection of ten of my favorite articles, so it gets a sense of what a “Techdirt article” looks like. On top of that, I give it a “Masnick Style Guide” that I had created after feeding a bunch of Techdirt articles into three different LLMs, asking for each to produce a style guide, and then having NotebookLLM combine them all into a giant “Masnick style-guide.”

Then, I feed it any links, including earlier stories on Techdirt, that are relevant, before finally writing out a prompt that can be pretty long. In this test case, I fed it the PDF file of the decision. I also gave it Techdirt’s previous stories about Judge Boasberg.

Finally, I gave it a starting prompt with a fair bit of explanation of what angle I was hoping to see a Techdirt post on this topic. So here’s my full prompt:

Can you write a Techdirt style first draft of a post (see the attached Techdirt post samples, as well as the even more important Masnick style guide, which you should follow) about the attached ruling in the JGG v. Trump case by Judge James Boasberg. I have also attached a page of previous articles about Judge Boasberg which you should consider, especially as some reference this same case.

You may also want to highlight that Judge Boasberg just was vindicated after the DOJ filed a vexatious complaint against him because of earlier rulings in this case, but that complaint has been easily dismissed. The crux of this article, though, should be on the very strong language Boasberg uses, including the astoundingly candid statement that he felt the government “apparently was no interested in participating in this process” and how he read their response as telling “the Court to pound sand.” There are other parts of the ruling that are useful as well. It should also call out the specific remedy here, and how weak it feels, given the situation explained in the ruling and the DOJ’s actions. Yes, they lost the case, but this still feels like a slap on the wrist with no real consequences for the DOJ.

As always with Techdirt posts, instead of doing in-line quotes, we usually do blockquotes, often of one or even multiple paragraphs from the original sources, so please adhere to that style. Take all of this info and draft the best Techdirt post you can regarding the topic.

And… you can see the results embedded below. I’ve also embedded my original article (though you can just go read it on the site directly). I’m amused that it added a “from the such and such dept” line as well as tags, both of which are core parts of Techdirt posts, but not things I asked it for.

I’m extremely biased, as this is a question of who writes better, me or the machine, and I still think I’m better than the machine. But, I also have to admit it’s not bad. It’s decent. If I had that submitted by another writer, there are definitely changes and edits I’d make, especially to the crappy cliche’d ending. But it’s way better than what most people think of as traditional ChatGPT output, in part because of all the context and detailed instructions I fed it.

Just for fun, I then also asked my editing tool to do its own edit on its own writing (usually not a good idea to let it grade its own homework), but here’s what it had to say:

solid draft. the “pound sand” framing works well and the frustration comes through. few things:

the tension setup: you flag “frustratingly toothless” in graf 3 then say “on one level this is a win” much later. that’s the right editorial instinct—there IS genuine tension here—but you’re burying the lede on your own argument. consider setting up that complexity earlier so readers know they’re getting nuance, not whiplash.

missing a key detail from the ruling: Boasberg notes that “even Plaintiffs’ counsel could not represent how many of the 137 are still in Venezuela and how many wish to proceed with habeas.” that’s devastating. the chaos is so complete that the lawyers literally don’t know where everyone is. worth including.

the numbered remedies block: you cut it off mid-list. the 5th point actually matters—there’s a March 13 deadline for the government to file a Status Report explaining how/when they’ll transport people back. that’s your next milestone. either include it or acknowledge you’re excerpting.

the Venezuela carve-out: you mention it but undersell it. the ruling specifically says it’s “mindful” of the “situation in Venezuela remains in flux” given “the United States’s recent law-enforcement action there.” that’s pretty ominous language from a federal judge about whatever the hell the administration is doing in Venezuela right now. might be worth a parenthetical noting this deserves its own article.

the closer: “I wouldn’t hold my breath” is fine but feels like boilerplate. you’ve got stronger material to end on—maybe the March 13 deadline, or something that points forward rather than just shrugging.

one small thing: “a complaint that was summarily dismissed” in graf 2—might want “recently dismissed” or similar since it was just last week. “summarily” suggests procedure when really the story is how embarrassing the dismissal was.

overall structure is good. the piece does what Techdirt does well: walks through the actual document, quotes liberally, and doesn’t pretend the “win” is bigger than it is.

You’ll note that it also calls out its own weak ending, just like I did. It is kind of wild to see the AI call out its own weaknesses, while making you wonder—if that’s the case—why did it not catch those earlier and fix them? And that then makes you wonder if it’s just coming up with a critique for the sake of giving one (though, that ending really is weak).

The other thing I’ll note is, again, this actually was still a fair bit of work. It was less than writing the whole thing myself, but even just writing out the prompt itself took time, and this piece would still need a fair bit of editing anyway for publication which would probably take away any time benefit.

Overall, though, you can see how the technology is certainly getting better. I still don’t think it can write as well as I do, but there are some pretty good bits in there.

Once again, this tech remains quite useful as a tool to assist people with their work. But it’s not really good at replacing your work. Indeed, if I asked the AI to write articles for Techdirt, I’d probably spend just as much time rewriting/fixing it as I would just writing the original in the first place. It still provides me very good feedback (on this article that you’re reading now, for example, the AI editor warned me that my original ending was pretty weak, and suggested I add a paragraph talking more about the conclusions which, uh, is what I’m now doing here).

I honestly think the biggest struggle with AI over the next year or so is going to be between the people who insist it can totally replace humans, leading to shoddy and problematic work, and the smaller group of people who use it as a tool to assist them in doing their own work better. The problems come in when people overestimate its ability to do the former, while underestimating its ability to do the latter.

For the last five years, we had to endure an endless, breathless parade of hyperbole regarding the so-called “censorship industrial complex.” We were told, repeatedly and at high volume, that the Biden administration flagging content for review by social media companies constituted a tyrannical overthrow of the First Amendment.

In the Missouri v. Biden (later Murthy v. Missouri) case, Judge Terry Doughty—in a ruling that seemed to consist entirely of Twitter threads pasted into a judicial ruling—declared that the White House sending angry emails to Facebook “arguably involves the most massive attack against free speech in United States’ history.”

Never mind that the Supreme Court later reviewed the evidence and found that the platforms frequently ignored those emails, showing a lack of coercion, leading them to reverse the lower courts for lack of standing. To the “Twitter Files” crowd and the self-anointed “free speech absolutists,” the mere existence of government officials simply requesting private companies to look at terms of service violations was a sign of the end of the Republic.

So, surely, now that the Department of Homeland Security is issuing administrative subpoenas—legal demands that bypass judges entirely—to unmask the identities of anonymous political critics, these same warriors are storming the barricades, right?

Right? Riiiiight?

According to a disturbing new report from the New York Times, DHS is aggressively expanding its use of administrative subpoenas to demand the names, addresses, and phone numbers of social media users who simply criticize Immigration and Customs Enforcement (ICE).

In recent months, Google, Reddit, Discord and Meta, which owns Facebook and Instagram, have received hundreds of administrative subpoenas from the Department of Homeland Security, according to four government officials and tech employees privy to the requests. They spoke on the condition of anonymity because they were not authorized to speak publicly.

Google, Meta and Reddit complied with some of the requests, the government officials said. In the subpoenas, the department asked the companies for identifying details of accounts that do not have a real person’s name attached and that have criticized ICE or pointed to the locations of ICE agents. The New York Times saw two subpoenas that were sent to Meta over the last six months.

This is not a White House staffer emailing a company to say, “Hey, this post seems to violate your COVID misinformation policy, can you check it?” This is the federal government using the force of law—specifically a tool designed to bypass judicial review—to strip the anonymity from domestic political critics.

If Judge Doughty thought ignored emails were the “most massive attack on free speech in history,” I am curious what he would call the weaponization of the surveillance state to dox critics of law enforcement. Or… would he think it’s fine, because it’s coming from his team?

As the Times reveals, this is really all about intimidation.

Mr. Loney of the A.C.L.U. said avoiding a judge’s ruling was important for the department to keep issuing the subpoenas without a legal order to stop. “The pressure is on the end user, the private individual, to go to court,” he said.

The DHS claims this is about “officer safety,” but documenting the public actions of law enforcement officers in public spaces is a foundational First Amendment right. The moment these subpoenas are actually challenged in court by competent lawyers, the DHS cuts and runs.

The account owner alerted the A.C.L.U., which filed a motion on Oct. 16 to quash the government’s request. In a hearing on Jan. 14 in U.S. District Court for the Northern District of California, the A.C.L.U. argued that the government was using administrative subpoenas to target people whose speech it did not agree with.

[….]

Two days later, the subpoena was withdrawn.

This is the government effectively admitting that its demands are legally baseless. They are relying on the high cost of litigation to intimidate both the companies and the individuals. It is a bluff backed by the seal of the Department of Homeland Security.

And this brings us to the most glaring hypocrisy of the current moment: the absolute silence of Elon Musk and X.

Years ago, the “old” Twitter—the one Musk falsely derided as a haven for censorship—was the gold standard for fighting these exact types of demands. In 2017, Twitter famously sued the federal government to stop an administrative subpoena that sought to unmask an anonymous account critical of the Trump administration. Twitter argued, correctly, that unmasking a critic violated the First Amendment. They won. The government withdrew the subpoena.

Twitter (the old company, not the new monstrosity known as X) has a long history of this. In 2012, they challenged a court ruling that said users had no standing to protect their data. In 2014, they sued the DOJ for the right to be transparent about surveillance requests.

Contrast that with today. The Times report notes that Google, Meta, and Reddit have received these subpoenas. It mentions that Twitter previously fought them. But there is zero indication that Elon Musk’s X—the platform ostensibly dedicated to “free speech absolutism”—is lifting a finger to stop this.

While Musk is busy personally promoting racist ahistorical nonsense, the actual surveillance state is knocking on the door, demanding the identities of political critics. And we’ve yet to see anything suggesting Elon is even remotely willing to push back on his friends in the administration he helped get elected, and then gleefully was a part of for a few months.

And where are the scribes of the “Twitter Files”? Where is the outrage from the people who told us that the FBI warning platforms about foreign influence operations was a crime against humanity?

Matt Taibbi, who has spent the last few years on the confused idea that platform moderation is state censorship, offered a tepid, hedging response on X, saying “if true” this is terrible, before immediately pivoting to a strange whataboutism regarding investigations into actual proven Russian attempts at election interference.

It is true, Matt. The New York Times saw the subpoenas. The ACLU is fighting them in court. This isn’t a vague “if.” This is the government using administrative power to bypass the Fourth Amendment to violate the First Amendment.

It seems like we actually found that “censorship industrial complex,” huh?

Meanwhile, Michael Shellenberger and Bari Weiss seem to have nothing to say. Weiss now runs CBS News, which has its own problems with government pressure on speech—the network just pulled a Colbert interview with a Democratic politician after Brendan Carr threatened consequences for talk shows that don’t coddle Republicans. As far as I can tell, neither CBS News nor Weiss’s Free Press has mentioned the DHS subpoena story. The Free Press is instead running think pieces on how we may “regret” the release of the Epstein files.

Really speaking truth to power there.

This is what so many of us kept pointing out throughout the “Twitter Files” hysteria: the “free speech” grift was never about protecting individuals from the state. It was about protecting a specific type of speaker from the social consequences of their speech. The framework was always selectively deployed—outrage when a platform enforces its own rules against their allies, silence when the surveillance state comes for their critics.

The Trump administration is betting on that asymmetry. They’re betting that Google, Meta, Reddit, and Discord will quietly comply rather than spend millions in litigation over users who aren’t famous enough to generate headlines. They’re betting that the “free speech absolutists” will look the other way because the targets are the wrong kind of dissident.

Right now, the only institution consistently fighting these subpoenas is the ACLU. The platforms are folding. The “Twitter Files” journalists are hedging. And the man who bought a social media company specifically to be a “free speech” champion is busy posting memes.

Turns out we found the censorship industrial complex. And everyone who spent years warning us about it just shrugged.