How Close Can AI Get To Writing A Techdirt Post?
Fascinating look at an advanced AI user's partnering with AI; however, studies show that humans still objectively retain the home court advantage of Judgment.
Wed, Feb 18th 2026 01:35pm - Mike Masnick
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’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, ....
https://www.techdirt.com/2026/02/18/how-close-can-ai-get-to-writing-a-techdirt-post/
= new reply since forum marked as read
Not being as advanced as Masnick or you, probably, but it seems important to be able to use prompts that optimize AI as a tool of humans so that humans themselves don't become tools of AI.