Milbank partner Neil Katyal raised eyebrows this week when he revealed in a new TED Talk that he is using AI tools to prepare his case against President Donald Trump’s tariffs before the U.S. Supreme Court.
Mr. Katyal, a former acting attorney general who has filed more than 50 cases in court, argued the case in November after winning a coin flip over another lawyer, Mr. Akin’s Pratik Shah. The court ultimately ruled 6-3 in favor of a coalition of companies challenging global tariffs.
“I stepped up to the mahogany podium and won,” Katiyal said in a speech published Thursday, before revealing what he called his secret weapon in case preparation: a “custom-built AI system” trained on 25 years of Supreme Court documents that was able to predict not only the justices’ questions but also their final opinions.
It is unusual for an advocate like Katyal to take so much personal credit for a Supreme Court victory, especially given that the case involved several elite law firms and dozens of court briefs, and his comments provoked a backlash from court watchers.
The backlash was immediate, with a flood of posts on social media and critical columns on the National Review website and the Volokh Conspiracy, a law blog hosted by Reason magazine.
“I think people just find the idea that Katiyal’s preparation with a mindfulness coach and AI made a huge difference a little bit ridiculous,” said Daniel Epps, a professor at Washington University School of Law in St. Louis.
Xiao Wang, director of the University of Virginia Supreme Court Litigation Clinic, said Katyal undoubtedly put his “blood, sweat and tears” into this case. But Wang, who argued twice before the justices, said the high court defenders were only part of getting the case across the finish line.
“I thought it was a little weird for a quarterback here to say there’s actually an ‘I’ on the team,” Wang said.
Mr. Katiyal, along with Mr. Milbank, did not respond to multiple requests for comment, but seemed aware of how his presentation would be received.
“I know how this sounds,” Katiyal said in a lecture filmed in Vancouver last month. “A lawyer wins a big case, gets an invitation to give a fancy TED talk, and gives a 14-minute talk about his greatness.”
That was not the case with his TED talk, he assured the audience. Rather, it was about the four coaches he brought in to help prepare him for better relationships with the judges. One is Harvey, a mindfulness coach, improvisation coach, meditation coach who worked with tennis great Andre Agassi, and an AI model that he said helped predict how judges think.
And while the TED Talk focused almost exclusively on his own preparations, in a social media post promoting it, Katiyal praised “the best legal team in the country” for assisting him, especially Milbank partner Colleen Law Sinsdak and the Liberty Justice Center, which organized the business plaintiffs.
Five months ago, I argued before the Supreme Court against the president’s $4 trillion in tariffs.
In 237 years, the court has never struck down a signature initiative by a sitting president. Legal scholars said that was impossible. Some of my own colleagues said it was impossible.
we won. pic.twitter.com/g3O0mw99ny
— Neal Katyal (@neal_katyal) May 6, 2026
tech talk
The rapid adoption of LLM and other AI tools is transforming the legal industry, especially as courts grapple with a penchant for citing hallucination cases. But Wang predicted that Supreme Court supporters, like himself, will increasingly use the technology in digital moot court, even if not many are using it yet.
Katyal’s AI “coach” was built by Harvey AI, a San Francisco-based company that creates large-scale language models for the legal industry. Mr. Harvey said his company’s client list includes Walmart Inc., Comcast Inc. and O’Melveny & Myers Inc., and that it was used to prepare at least other Supreme Court cases this quarter.
A Harvey spokeswoman said in an email that there is no arrangement with Mr. Katyal to promote the company’s services, and he does not hold any investments or equity interests in the company. Katiyar did not respond to a request for comment Friday.
In his TED Talk, Katyal displayed Harvey’s anticipated questions along with excerpts from the actual oral argument transcript, saying some were “almost verbatim.” He also credited the tool with identifying a “way out” to get Chief Justice John Roberts on his side in the case.
“Harvey glanced at the narrow door, I held it open, and the Chief Justice walked through,” Katyal said.
Epps, who clerked for Justice Anthony Kennedy, echoed other critics who said the comment gave the impression of “arrogance” and could damage Katyal’s standing with the justices.
“I think he really undermined the credibility of the judges,” Epps said, adding that Katiyal sounded as if he was saying he could manipulate the judges to change their votes.
Still, Mitu Gulati, a University of Virginia law professor who studies the Supreme Court, said Katyal’s presentation highlighted the potential value of AI-driven predictive tools.
Gulati said advocates value consistency among judges, and the fact that AI models can identify patterns in judges’ questioning and reasoning is reassuring.
“Regardless of the argument, it doesn’t mean they’re results-oriented,” Gulati said.
Gulati said that even though Katyal was exaggerating the role of AI models, the meeting ultimately highlighted the preparation and track record skills that have made Katyal the go-to lawyer for high-stakes Supreme Court cases.
“Everyone reads everything, and it’s hard to imagine oral arguments changing anyone’s vote,” Gulati said. “But if you can change your vote, you should pay someone to do it.”
