Joe Regalia Profile picture
Jun 6, 2022 8 tweets 3 min read Read on X
Check out the cool writing choices made by the stellar #legalwriting teams at @WinstonLaw and @Kirkland_Ellis in this single-paragraph introduction kicking off a reply filed today.

Even replying, these pros package everything readers need into a powerfully-written package. 1/x Image
Verbs chosen with care: Not what most would write (the statute is applicable only to...). Instead, the subject is an actor (the Supreme Court) and it's carrying out actions that push the advocacy points (narrowing, requiring, demanding, urging to criminalize...). Image
Choosing persuasive labels for concepts that push advocacy points. "Commonplace gratuities" hits differently than "payments," or even just plain "gratuities." Image
Echoing words in a key sentence so that it stands out from the background. How many times have you read lawyers writing about "alleged quids"? Probably never. And so readers are likely to notice and remember. Image
Using examples to make powerful points. Noting that the punishment is "five times" as much as other provisions may not be legally relevant, but it's a choice example that makes hits hard. Image
Subtly weaving in policy-based details: Like mentioning that the government's pitch would create the "one" immune statute. And a hypothetical with a parade of horribles: If the government were correct...look at the bad things coming. These are simple tools you can apply! Image
This last one is so powerful when you can show that other settled cases would have turned out differently if only the lawyers had mentioned an argument...
I also love when legal writers suggest that the other side is arguing for the opposite of [insert thing we care about--policy, settled law, holding, congressional intent, and so on]

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More from @writedotlaw

Mar 4
Agents are changing the game for lawyers.

If you’re still thinking about “prompt engineering” as a spell-casting exercise, you’re already behind.

Let’s slow down and get clear on what’s actually happening. 🧵
An agent is a system that can break a task into sub-tasks, decide what to do next, evaluate intermediate outputs, and revise its own work.

Instead of one prompt and one answer, you get a loop.

Think less “question and answer” and more “junior associate with a workflow.” (2/7)
The new reality: workflow > wording.

When you’re using an agent, the real leverage is upstream and downstream:

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Feb 27
The Supreme Court just heard a major case: whether the President can use a 1977 emergency-powers statute to impose tariffs.

The private respondents—represented by Neal Katyal and a team of elite advocates—filed a merits brief that reads like a legal writing masterclass.

🧵
☑️ Open By Telling a Story, Not Stating a Rule

Most lawyers launch their briefs with procedural history or legal standards.

The best legal writers do something different—they tell a story first. Before readers can care about your rule, they need to care about the stakes. (2/6) Image
☑️ Turn Your Opponent’s Own Words Into Your Best Evidence

There’s no more devastating move in legal writing than using the other side’s own words against them.

When your opponent concedes a point, don’t let it slide by—put it center stage. (3/6) Image
Read 6 tweets
Jan 3
Most lawyers spend more time fighting Microsoft Word than using it.

That frustration usually gets chalked up to Word being “quirky.” It isn’t.

Here are the Word tools and skills that actually matter for lawyers and power users in 2026. 🧵
☑️ Start by Letting Styles Do the Heavy Lifting

If you format headings by changing font size and bolding text manually, Word treats every heading as unrelated.

That’s why numbering breaks, tables of contents fall apart, and cross-references stop updating. (2/7) Image
☑️ Fix Numbering the Way Word Expects You To

Legal numbering fails when people click the numbering button and hope for the best. Stable numbering comes from multilevel lists linked to heading styles.

The correct workflow looks like this: (3/7) Image
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Dec 5, 2025
Kirkland & Ellis’s brief in the blockbuster AI case, Thomson Reuters v. ROSS, lands like a masterclass.

It shows how advocates frame a narrative, marshal facts, and push the reader toward one inescapable conclusion.

Let’s unpack the writing techniques that make this one hum. 🧵
1️⃣ Choose a Frame That Carries the Whole Story

Kirkland doesn’t warm up. It opens with the entire case in a single hit. (2/8) Image
2️⃣ Distill the Point Before You Dive Into the Details

Great briefs announce the takeaway before the reader ever has to work for it. Kirkland does this over and over. (3/8) Image
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Aug 5, 2025
If you’re still unsure where GenAI fits in your legal writing, start here: summarizing and restyling.

Why these two? Because you’re feeding the tool your own material. Full control. Low risk. High reward.

Here’s how to do it right 👇 (1/8)
1⃣ Summarizing: Compress Without Losing the Thread

GenAI is fast and ruthless when it comes to boiling text down. Give it a long court opinion or a five-page email chain, and it’ll give you something short, useful, and readable. As long as you tell it how. (2/8)
➡️Prompt: Summarize a Court Opinion for Internal Use

You’re giving the model a role, a clear goal, sectioned instructions, and formatting constraints. That reduces fluff and hallucination. (3/8) Image
Read 8 tweets
Dec 23, 2024
The best legal writers are those with the biggest boxes of authority evidence.

These attorneys can work creatively to make readers question, even when a precedent seems like it binds the result.

Here are five tools to help you start filling your authority-evidence toolbox. 🧰
1️⃣ Use multiple types of authority evidence for key points.

Often it’s more persuasive to combine multiple types of authority evidence—a quote, a comparable fact, and so on—rather than relying on only one dimension of an authority. (2/6) Image
2️⃣ Quote authority.

Use quotes to illustrate how rules work. As with all quotes, use the smallest portion of text that will illustrate the most useful information. (3/6) Image
Read 6 tweets

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