Supreme Court Briefing in the Year 2030

I had a dream last night that it was 2030. I was doing a virtual-reality-cast about how briefing Supreme Court cases has changed since the 20th Century. Here’s what I remember saying in the dream:

Robot45, thanks, it’s a pleasure to be here! I’m one of the old-fashioned dinosaurs from the MSB — Main Stream Blogosphere — so trying out a virtual-reality-cast is a new experience for me. What they say is true. It really does seem real.

You’ve asked me to talk about changes in how Supreme Court cases are briefed. Back around the turn of the century, most of it was on paper. Hard to believe, but true. The parties would write little books called briefs, and then submit them on paper. The only interaction between the lawyers and the Justices was the one-hour oral argument.

That changed around 2015, when litigants started to regularly host websites that would present their views of the case and respond to questions. The idea started as a place to host briefs, newsclippings, and generate media interest in favor of a case. But it soon evolved and expanded. Eventually, lawyers started regularly creating podcasts to explain their arguments. This let litigants both have short summaries of their cases (for the public) and also to go into remarkable detail about their cases (for lawyers and those interested).

The practice became regularized as it became clear that such websites were a way to communicate with the Court itself. The turning point is widely thought to be United States v. Grouse, handed down in 2018. In Grouse, an inexperienced advocate named John Hendelberry struggled greatly at oral argument and was widely thought to have lost the case. The next week, however, Hendelberry started writing a series of updates to his website — blog posts really — that were widely read among Supreme Court fans. Hendleberry’s essays responded to the questions he was asked at oral argument, and they were widely celebrated as quite persuasive. When Grouse was handed down, the Supreme Court’s opinion closely tracked Hendleberry’s discussion on his website.

After Grouse, many Supreme Court advocates started to post so-called “Hendleberry essays.” (As Black’s Law Dictionary now states, a “Hendleberry essay” is defined as “a public statement posted on the Internet, written by an attorney with a pending appellate case, that responds to questions raised and elaborates on arguments at issue in the case.”). In some cases, the two parties had competing websites, which as a matter of courtesy linked to each others’ site. In other cases, the parties would make a Hendleberry agreement and create a joint site. They would then agree as to format, length, frequency, and the like.

The Supreme Court formally recognized Hendleberry essays just five years ago, in 2025, at the urging of Solicitor General Tom Goldstein. The new rule is Rule 24.1, designated Supplemental Materials. The new rule formally permits parties to create public sites that provide additional materials and respond to public comments, additional briefing, and responses to oral argument, either with an eye to influence the public, the press, or the Court itself. (Such sites were seen as informally permitted before the rule change, but they made some lawyers uncomfortable. The rule change was designed to clarify that such sites are okay.)

So that’s how briefing has changed. It used to be just one round of paper briefs and one hour of argument. It’s now much more of an ongoing conversation, most of it via the Internet. The downside is that it’s a lot more work, as there isn’t just one brief to read. (That’s one of the reasons each Justice gets 9 law clerks now.) But the upside is that decisions are better: There is more high-level discussion of the issues by the parties, and more and better-developed briefing about the arguments even outside the formal limits of the briefs.

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