Mastodawn

A woman sues her insurance company for terminating her disability benefits. They reach a settlement and agree that the suit will be dismissed with prejudice.

She decides she doesn't like the settlement and asks her lawyers to reopen the case.They say they can't: it was dismissed, and in the settlement she agreed not to reopen the case.

She asks ChatGPT if her attorneys are lying to her. It says they are. She fires them and continues pro se, advised by ChatGPT.

CharGPT generates legal arguments for reopening the case, which she files, and 21 more motions, a subpoena, and eight other notices and statements, which she files.

The court denies her motion to reopen the case.

Advised by ChatGPT, she files a new suit against the insurance company and submits 44 more motions, memoranda, etc., which include citations to nonexistent cases.

Now the insurance company has sued OpenAI for tortious interference with their settlement contract.

🍿

https://storage.courtlistener.com/recap/gov.uscourts.ilnd.496515/gov.uscourts.ilnd.496515.1.0_1.pdf

Mark Dominus Mar 13

“OPENAI, through its AI chatbot program ChatGPT, provides legal advice, legal analysis, legal research and can draft legal documents and papers for submission to a Court. ChatGPT provides these legal services to any user who requests them. ChatGPT is not licensed to practice law in Illinois.”

They're asking for declaratory judgement that OpenAI has been practicing law without a license, a permanent injunction barring them from providing the disgruntled woman with any more legal assistance, $300,000 to reimburse their costs in responding to the bogus motions, and $10 million in punitive damages.

David Zaslavsky Mar 13

@mjd hahahahahahaha

(not mocking laughter, it's a shame that this happened to the woman, it's just that this fight between two big corporations promises to be both legally enlightening and very entertaining)

Mark Dominus Mar 13

@diazona I don't think it is a shame that this happened to this woman. It appears that she is a very ordinary type of vexatious litigant, except that she is also being aided by ChatGPT.

David Zaslavsky Mar 14

@mjd Yeah fair point... I was thinking more along the lines of, whatever happened to her (possibly long ago) to put her in the frame of mind to pursue this case regardless of the legal merits, and to believe ChatGPT over actual lawyers, is a shame. But I'm definitely not trying to absolve her of responsibility for her actions and their consequences.

Mark Dominus Mar 14

I agree with you 100% on the hahahahahahaha 🍿 thing though

WellsiteGeo Mar 16

@mjd @diazona Though I'm not a lawyer (thank Cthulhu, or belly rubs to it's acolyte Menhit @antipope_cats) I do recall the Scottish courts taking exception to a "vexatious litigant" a while ago. It ended badly for said litigant.

tessarakt Mar 14

@mjd the punitive damages seem a bit on the low end.

@mjd they also, AIUI, accuse OpenAI of generating spam that allows the abuse of the justice system. It's interesting how the legal universe will respond to the diminishing cost of writing legal text that sounds like something maybe worth attention. I guess the high cost of generating such text had shielded courts from flood until recenty.

milla🧷Mar 16

"It's interesting how the legal universe will respond to the diminishing cost of writing legal text that sounds like something maybe worth attention."

Remove the word "legal" and this applies to all LLM output. There's more and more text and less and less of it is worth reading.

@milla @mjd yeah but most other professions either cannot be DDoS'ed by such texts (an engineer isn't required to read any report that comes to their desk), or have already developed methods to deal with it (email anti-spam comes to mind).

A court however has to process any suit filed that follows the correct form. (Forgive me if I'm using the wrong terms, not a lawyer and not a native English speaker) I guess what kept the courts from being utterly disabled was the cost of producing something that looked like a legit suit.

Mark Dominus Mar 16

@qwazix @milla I wonder if the result will be that AIs do pre-filtering on the filings before they go to a human clerk for final vetting.

At least one credible person thinks this would work.

https://adamunikowsky.substack.com/p/in-ai-we-trust
https://adamunikowsky.substack.com/p/in-ai-we-trust-part-ii

In AI we trust

AI is already able to decide cases correctly.

Adam's Legal Newsletter

@mjd @milla I find it hard to even read an article that asserts that "This is not a drill. Right now, present tense, AI can accurately decide cases and write judicial opinions."

Mark Dominus Mar 16

@qwazix @milla Coincidentally, the same guy published another article today suggesting the same thing!

“If everyone fulfills their role—if the lawyers try their best to be both persuasive and credible and the judge tries to resolve the dispute as accurately as possible—then we’ll have AI deciding between two AI-written submissions, with the human lawyers claiming that their submissions are credible precisely because humans were not involved. So much for our legal system.”

“On the other hand, the current situation is not much better. The government claims it has no choice but to keep billions of dollars in illegally-exacted tariffs, and there’s nothing anyone can do about it. ”

“Pick your poison!”

https://adamunikowsky.substack.com/p/pick-your-poison

Pick your poison

How hard is it to refund the tariffs?

Adam's Legal Newsletter

@mjd @milla that translates directly into "one of the three AI companies decides" because who would pass up a chance to surreptitiously steer the whole legal system.

Colin Rowat Mar 13

@mjd has she sought a second opinion (e.g. unfrozen Grokman lawyer)?

Colin Rowat Mar 14

@mjd Levine (12/03/26):

Here’s a Perkins Coie memo from last month:
> On February 17, 2026, the Southern District of New York, in United States v. Bradley Heppner, held that a criminal defendant's written exchanges with a “publicly available AI platform” are not protected by attorney-client privilege or work product doctrine and, thus, could be inspected by the government.

Mark Dominus Mar 14

@rowat_c Wild times we live in.

@mjd on LinkedIn I saw a breathless post about how the professionals of the future are using autonomous agents to do all this magic....

Then I come back here for a reality check

Mark Dominus Mar 15

@krupo It's an interesting time. Many of the successes are overstated. So are many of the failures. Nobody knows how it will shake out in the end.

millennial fulcrum Mar 16

@mjd @krupo it will be a financial bubble pop, followed by what we will call 'the AI recession,' then limited, appropriate use. the shit is the dot com and GFC playbook all day.

millennial fulcrum Mar 16

@mjd @krupo that MIT article demonstrated 5% of AI implementations are profit making. 95% are loss making. so when the investment goldrush mania ends or winds down, 95% of invested amounts will be wiped out. it's billions so it will have a disruptive and negative economic effect that I think we will likely experience as recession. and then that 5% of profit making implementations will be what carries forward, with further investment being modelled on those (anyone can do that right now).

WellsiteGeo Mar 16

@falcennial @mjd @krupo
Looking to the foreseeable future, the AI boosters (especially those using AI to write their "opinions") will blame the bubble-burst on the Trump-Bibi War (no, they can't escape the blame) and *it's* crash.
How much are Darien Scheme share certificates worth these days?

Bill, organizer of stuff Mar 15

@mjd The only use case for Generative AI is fraud.

Mark Dominus Mar 15

@wcbdata That is demonstrably false.

Bill, organizer of stuff Mar 15

@mjd Try me. There isn't a use case for it that isn't, at its core, fraud.

Bill, organizer of stuff Mar 15

@mjd Couldn't think of even one reasonable candidate in 15 minutes, even with your precious AI right there in front of you? I rest my case.

Marsh Ray Mar 15

@mjd “41. On October 29, 2025, OPENAI amended the terms and usage policies of ChatGPT to prohibit users from using ChatGPT to provide tailored legal advice. Prior to the October 29, 2025 emendation, ChatGPT’s terms of use did not prohibit users from using ChatGPT to draft legal papers, conduct legal research, provide legal analysis or give legal advice.”

Mark Dominus Mar 16

@marshray I wonder if that will help get them off the hook. If not, it shows that they were aware that what they were doing could be a problem.

Q.H. Stone Mar 16

@mjd @marshray But they didn’t do anything to stop it.

WellsiteGeo Mar 16

@marshray @mjd
Any dates for the (alleged, legal modesty board) AI legal advice?

What's that, Lassie? You hear the sound of distant hard-drive shredders working overtime?

Marsh Ray Mar 16

@WellsiteGeo @mjd <https://storage.courtlistener.com/recap/gov.uscourts.ilnd.496515/gov.uscourts.ilnd.496515.1.0_1.pdf >

Simon Richter Mar 16

@mjd Wouldn't that be "tortuous inference"?

millennial fulcrum Mar 16

@GyrosGeier @mjd torturous interference

Simon Richter Mar 16

@falcennial @mjd I mean, because running an AI model is called "inference."

Mark Dominus Mar 16

@falcennial @GyrosGeier They're all closely related. They're from the Latin verb “to twist”.

fan boy 🪭Mar 16

@mjd
> They reach a settlement and agree that the suit will be dismissed with prejudice.

It's done, put a fork in it.

samiamsam Mar 16

HA!!!!!!!