is only a sliver of what dictates outcomes. What’s more, lawyers stuck with bad law, bad facts, or both are less likely to win and more likely to feel forced into writing choices that could muddy the pool of losing briefs. Think of how Supreme Court justices often write more vividly in dissents than when they have to win over skeptical colleagues. For the data analysis, I retained part of a team that developed an algorithm to predict which Supreme Court justice wrote an opinion. Here Are Some Ground Rules First, artificial intelligence and machine learning are fantastic tools, but you need human expertise too. A simple example: The phrases “default judgment” and “trust assets” appeared much more often in the random set than in the heavy-hitter set, but those differences reflect the subject matter of the litigation. You also need expertise to ferret out the take- aways behind the data. What’s going on in the lawyers’ minds that draws them to the best writing choices? And if great legal writing is more than just “I know it when I see it” or even just “Write short and to the point,” what do the data suggest you can do to make readers happier—and more persuadable? Second, relative rates are what matters. Almost any word, phrase, or device can work sometimes. So if you look at the right-hand columns in the tables below and ask, “Isn’t such-and-such OK when you . . .?” the answer is probably “yes.” Again, it’s all relative. Third, gaming the system doesn’t work. If you take an in- effective brief and sprinkle in some “good” words and devices below, it will be just ineffective. The analysis applies only to ac- tual filed work product that grapples with real facts and real law. Finally, the analysis doesn’t consider quoted language. Now, on to what artificial intelligence and I discovered together. Let’s begin with some conclusions that might surprise you. Myth busters, you might call them. On average, the top brief-writers, both trial and appellate . . .
• do NOT write shorter sentences. • do NOT write shorter paragraphs.
• do NOT file shorter briefs or motions. (In the October 2018 Supreme Court term, for example, members of the elite Supreme Court bar who ultimately prevailed on the merits submitted longer merits briefs on average than any other group.)
Illustration by J.F. Podevin
Published in Litigation, Volume 46, Number 4, Summer 2020. © 2020 by the American Bar Association. Reproduced with permission. All rights reserved. This information or any portion thereof may not be copied or disseminated in any form or by any means or stored in an electronic database or retrieval system without the express written consent of the American Bar Association. 2
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