Sullivan & Cromwell’s Robert Giuffra on AI, Mamdani, Font Choice

Sullivan & Cromwell co-chair Robert Giuffra Jr. worries that the legal industry’s golden age is over.

“Maybe everybody will just have dueling briefs that’ll come out of some Elon Musk-created AI system,” he said in an interview last week. “I hope not, but who knows what the future holds.”

A nearly four-decade litigator at the Wall Street firm, Giuffra is representing President Donald Trump in appeals of Trump’s hush-money conviction and civil fraud penalty. (He declined to discuss those cases.)

His past work includes representing Volkswagen in the German automaker’s years-long emissions-cheating scandal and defending Goldman Sachs in litigation arising out of the financial crisis.

He told Bloomberg Law what’s on his mind and on his bedside table heading into a potentially tumultuous new year for lawyers.

This conversation has been edited for length and clarity.

AI, Specialization

Q: What’s the biggest challenge facing lawyers in 2026?

The profession has become very specialized. Young lawyers are being forced to pick their specialty really early.

And for litigators, there’s not as much in the way of trial experience. In the bigger cases, clients want more senior lawyers to do the heavy lifting to a degree that’s different than it was 20 years ago.

We as a law firm are against specialization. We encourage generalists. I think our recruiting reflects that, because a lot of younger lawyers, particularly more talented ones, don’t want to be pigeonholed.

I think we’ll get to the point where AI will write briefs, oral argument outlines, cross-examination outlines, opening and closing statements, slides for trials — all the things lawyers spend enormous amounts of time on. It may not happen in two years, but it could happen in 10.

We could end up with a situation where after my generation is gone, one, you won’t have a lot of lawyers with a lot of generalist experience and, two, there’s no training for younger lawyers. A lot of the work that we did when we were younger, like learning how to do legal research, you won’t need to learn because you can just put a question into a computer and out comes a perfect memo.

I may have been lucky to practice law during the golden age. Technology has eliminated a lot of the drudge work that lawyers did, but the question is going to be could they be replaced by AI.

Is the golden age of being a lawyer over?

I worry about it. It may be better, though. It may become a new golden age, where lawyers are only doing really high-end analysis and high-end advocacy and less drudge work.

But the problem is you’ve got so many lawyers going into the profession. I think there’s going to be more stratification. You’re going to have elite firms, and then what happens to the firms that are doing more commodity work? There could be less demand for them.

Why couldn’t a computer do due diligence for an IPO or draft a merger agreement?

Mamdani, Arial-18

What New York law would you add or repeal?

New York City rent control laws. We have a housing crisis in New York City, and I think the premise that underlies those laws, that the government can control prices, doesn’t make any economic sense. It’s politically popular, but I think it doesn’t have the effect of actually giving private developers the incentive to build housing, and particularly lower-income housing.

So the city ends up with two separate markets. One is market-driven and one is regulated. It hurts young people and people new to New York City who don’t have the benefit of getting the rent-controlled apartment.

I take it you’re not a Mamdani voter?

I have my doubts about what he’s proposing.

What book is on your bedside table?

“Golf Is Not a Game of Perfect” by Bob Rotella. He’s the premier mental coach for golfers. It’s got a lot on positive thinking, visualization, not being too focused on technique, enjoying the moment — principles with broader application than just playing golf.

I find lawyers who come up to the podium with a big binder of documents or a very long outline invariably are not able to speak in the moment, respond to questions, or deal with whatever the judge is thinking about.

I have a methodology that I use — very short talking points in Arial 18-point. I learned when I worked in Washington that that’s what a lot of politicians use for speeches and such. You’ll see somebody with an outline in Times New Roman 10-point, and they can’t read it. They’re looking down. If I have the talking points in 18-point Arial, I can look at it, and it doesn’t even look like I’m looking down.

On Sleeping Well

Which of your past cases keep you up at night?

I never think about my past cases. I focus on cases that I’m dealing with right now.

We’ve settled cases that were hard cases because it was smart to settle, but I can’t remember one that ended disastrously. The only client I had that went to prison was Al Pirro. We negotiated a resolution after he was convicted. He served less than a year and ended up getting his law license back, so it was a good result.

Are you someone who tosses and turns? Or you go home for the day and you leave work at work?

I sleep pretty well. I had an argument representing Argentina in an $18 billion appeal, and I slept fine.