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Culture War Roundup for the week of February 9, 2026

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And, in the end, an LLM isn't deciding the motion or the case. Its typically a judge. Know your judge (or jury) is often the most important thing. When I was in law school I had a stubborn progressive con law professor that would always waive me off when I asked whether Justice Kennedy (or sometimes I'd use Frank Easterbrook as my example) would find this argument compelling. But that is kinda the whole game. When I was doing a lot of chancery work I had basically 4 judges where all my cases were. A winning argument in Judge 1's room is often not one in Judge 2's. Its not that they eventually apply the law all that differently, the opinions look the same, but what emphasis sways them is very important.

This is, IMO, even more prevalent in some of the high volume types of courtrooms. Criminal law particularly. You could have two defendants fairly similarly situated, and Prosecutor 1 could ask for 3 years on a gun case and the judge gives the Defendant 1, while Prosecutor 2 asks for 5 and gets it. How? Maybe 2 knows the judge has particular prior convictions he cares a lot about, or maybe the Defendant has a lot of arrests where he got off and thats what the judge cares about. One judge I knew hated all guns, but was deathly afraid of being called a racist in the press. So the way to get him to give longer sentences on felon with gun cases was to convince him the gun itself was particularly dangerous, while ignoring why the defendant was dangerous. That way he could say something like, "this gun belongs in Ft. Bragg in the hands of a trained soldier, not on the streets of our city in the hands of an untrained felon."

And an LLM will never figure that out.

And an LLM will never figure that out.

An LLM could absolutely figure this out. The technique is to have the llm create a file on each judge to update with perceived biases. It would not only figure this out but it might figure it out more completely and more thoroughly than any human could. This is in fact some of the stuff they're actually super human at. They can detect Russian ESL speakers in 6 words of a prompt, you think they can't scan through a history of judgements and find exploitable biases? Their most useful quality is that they are inhumanly patient and willing to do ungodly amounts of legwork.

Yeah, I don't think non-professionals realize that for most issues there's a lot of leeway with particular questions and the answers are unlikely to be resolved on appeal since most judges encourage the parties to settle and the parties are going to settle unless either things go completely off the rails or they really want a favorable appellate ruling and are willing to risk a multimillion dollar verdict (or long prison sentence) to get the answer. I'd also add opposing counsel to the list of relevant people that LLMs will never be able to understand. The bulk of my job consists of analyzing facts so I can figure out how much the case is worth from a settlement standpoint. Unless you've settled a few cases you aren't going to have any idea how much yours is worth. And I'd assume that most pro se litigants would insist that their case is worth either full value or nothing, depending on what side they're on. You may think you have a good argument, but chances are that a professional wouldn't take it to trial unless they absolutely had to.

I think a lot of attorneys are actually really bad at settlement, and its a place I think LLM might help them. Some are just absurdly overconfident in their chances of winning a case, and also of their own estimates as to damages.