In November, I attended the oral argument in the tariff case. I wrote a lengthy post about how I perceived the case. Ultimately, my bottom-line prediction was wrong. Trump would not get to five votes, let alone four votes. But I did have the occasion to reflect on the advocacy in the case. Here is how I described Neal Katyal's performance:
[S]everal Justices seemed skeptical, and even frustrated by Neal Katyal's presentation. He was polished, but wooden. Far too often, it seemed like he was giving rehearsed answers, which were not entirely responsive to the questions that were asked. Katyal may have also misread the room, and came in far too overconfident after the Solicitor General sat down.
I then explained how Katyal frustrated several justices, including Justice Gorsuch, who ultimately ruled against the government. At one point, Gorsuch said, "Well, you're not answering my question, though, Mr. Katyal." When Gorsuch asked about the Indian Commerce Clause, Katyal said, "I don't know that I have a position on that. It maybe is a little too afield for me to…" I observed: "Who played Justice Gorsuch in Katyal's moots? Did no one bring up the Indian Commerce Clause? General Sauer addressed this point directly during his rebuttal, so the government was ready." At another point, Justice Barrett asked a question about licenses that Katyal completely missed. He said, "Sorry. Could you say that again?" Katyal then had to back off and say he didn't concede something. Barrett chided, "Okay" with a tinge of sarcasm.
I closed my post with a reference to Jason Willick's Washington Post editorial, urging Michael McConnell to argue the case. I wrote:
Prior to the argument, Jason Willick wrote that Michael McConnell should have taken the podium instead of Neal Katyal. He explained that the respondents should have selected the conservative McConnell over the "partisan liberal lawyer." With the benefit of hindsight, I think Willick was correct. Michael McConnell clerked with Chief Justice Roberts the term that Dames & Moore was decided. He served with Justice Gorsuch on the Tenth Circuit. He traveled in the same law professor circles as Justice Barrett. McConnell would have been uniquely situated to bring this argument forward. And it would have been so much more powerful for an actual proponent of the separation of powers to argue this case. Indeed, at one point, Justice Alito ridiculed Katyal for making a non-delegation doctrine argument that he likely would not raise in any other context. Alito said, "I found it interesting to hear you make the nondelegation argument, Mr. Katyal. I wonder if you ever thought that your legacy as a constitutional advocate would be the man who revived the nondelegation argument." An uncomfortable laughter followed. Even Justice Kagan, who was Katyal's former boss, suggested that one of his arguments "cuts against" him.
I don't think Katyal was the right advocate for this job. If the government prevails, I think eyes will turn to him.
It's true that Katyal's side won, and he got 6 votes. But I don't think his advocacy had much to do with it. Any other competent member of the Supreme Court bar could have won that case. Indeed, I thought the Oregon Solicitor General, Benjamin Gutman, who had never argued before the high court, was more effective than Neal Katyal.
Anyway, I hadn't given much thought to the argument until I saw Katyal tweet about his imminent TED Talk:
Five months ago, I argued against the President's $4 trillion tariffs at the Supreme Court.
In 237 years, the Court had never struck down a sitting President's signature initiative. Legal scholars said it was impossible. Some of my own colleagues said it was impossible.
We won. 6-3.
But the real story isn't what happened in that courtroom. It's what happened in the months before. And its the subject of my TED talk, coming out tomorrow.
I had the best legal team in the nation, especially Colleen Roh Sinzdak, the most outstanding legal strategist I know. Huge thanks, too, go to the Liberty Justice Center (and in particular its fearless and hyper-intelligent leader Sara Albrecht), who organized the client small businesses, as well as to the brave small businesses themselves.
I also had four teachers preparing me.
A mindset coach who'd worked with Andre Agassi.
An improv coach who taught me that "Yes, and" works in Supreme Court arguments the same way it works everywhere else.
A meditation coach who taught me stillness.
And Harvey.Harvey predicted many of the questions the Justices asked — sometimes almost word for word. Brilliant. Tireless. Occasionally insufferable.
Here's the catch: Harvey isn't a person.
Harvey is a bespoke AI I built over the last year with a legal AI company, trained on every question every Justice has asked in oral argument for 25 years, and everything they've ever written.
Tomorrow, TED releases my talk about what really happened — and what I learned standing at that podium.
AI can predict. AI can analyze. What AI cannot do is the one thing that actually won the argument.
Connect. Read the room. Hear not just a Justice's words, but her worry — and answer the worry.
That is the irreducibly human skill.
Find yours. Go deeper. In this age of AI, that's where your edge lives.The talk goes live Thursday, May 7 at 11am ET: http://go.ted.com/nealkumarkatyal
What's the irreducibly human skill in your work — the thing AI can't touch?
Harvey is not the only thing insufferable about that tweet. Really, the posting looks like it was drafted by AI. Could the Ted Talk be even worse? Yes, it can. I thought of how best to break it down, and settled on simply annotating the transcript. If you want to read on, please do, but I won't blame you if you skip it.







