Evaluating Expert SCOTUS Briefs Based on Rules of Legal Writing

Do top Supreme Court advocates follow tried and true legal writing techniques?

Chief Justice Roberts provides a simple test for advocacy: “I have yet to put down a brief and say, ‘I wish that had been longer.’” He has also said that bad writing forces judges to “hack through a jungle,” while a good brief carries you along. Great Supreme Court lawyers understand that. They lead with an answer, argue in their headings, and write sentences that can guide the justices in their decisions.

This article uses transparent rules derived from legal writing scholarship to develop a 100‑point scorecard—the 12‑Law Writing Score. Like a previous post on this Substack, it then trains an LLM on those rules based on this defined scoring rubric to generate an overall score for each brief. The five main briefs are from:

· Kannon Shanmugam in Warner Chappell Music

· Lisa Blatt in A.J.T. v. Osseo Area Schools

· Paul Clement in Glossip v. Oklahoma

· Neal Katyal in Coinbase v. Bielski and

· Seth Waxman in NCAA v. Alston

To validate the coding outside of the elite members of the Supreme Court Bar, I randomly selected two additional briefs from the 2022 term from non-repeat Supreme Court players. These were:

· Lawrence Robbins in Health and Hospital Corp. v. Talevski

· James Barney in Arellano v. McDonough

This all comes with the caveats that these counsels of record are not the only authors in each brief, and the topic of each brief may somewhat dictate how a brief is written. It is entirely plausible that other attorneys listed on each brief had large roles in brief drafting. Still as counsels of record these attorneys take on a supervisory role so whether they write certain sections or oversee the writing, they are responsible for the output. As for brief topics, legal writing rules are consistent and agnostic to topic and so while topics play obvious roles in language choice, these should not force the authors to deviate from certain legal writing mores.

How It is Scored

This method uses a 100‑point score. Ten things carry the points: saying the answer up front, headings that tell the reason, a clear rule with a short explanation, step‑by‑step analysis that uses “because,” a fair treatment of the other side, a clean fact section, clear sentences, economy, smooth flow, and clean citations. Most items are worth two points; a few are worth a bit more. It removes all the points in a category if a brief misstates the record, hides a controlling case, or argues in the fact section. Simple software helped us spot mechanical tics; people did the reading and the judging.

These rules were extracted from the following articles

· 10 Tips for Better Legal Writing (ABA 2019)

· How Judges, Practitioners, and Legal Writing Teachers Assess the Writing Skills of New Law Graduates: A Comparative Study (Susan Hanley Kosse & David T. Ritchie 2003)

· Style Matters: A Review Essay on Legal Writing (James Lindgren 1982)

· Toward a Unified Grading Vocabulary: Using Rubrics in Writing Courses (Jessica Clark and Christy DeSanctis 2013)

· Critiquing and Evaluating Law Students’ Writing: Advice from Thirty-Five Experts (Anne Enquist 1998)

· Eight Strategies That Enhance Legal Writing (Douglas Abrams (2021)

· Scribes Journal Supreme Court Interviews with Bryan Garner (2010)