Interview with Samuel Issacharoff
Samuel Issacharoff is an American legal scholar and lawyer. He is the Bonnie and Richard Reiss Professor of Constitutional Law at New York University School of Law and was a senior legal advisor to the presidential campaigns of Barack Obama.
Lt. Robert Bork Behind Enemy Lines
Contents
Max Raskin: You were one of my great teachers in law school, and I wonder if you had any favorite teachers either from college or law school.
Samuel Issacharoff: I thought the most intense experience I had in education was my first year of law school, and I had two teachers that were shaping influences on me. One was my civil procedure teacher, Owen Fiss, who was this forceful sense of the possibilities of law, and I still can hear his voice in my head.
MR: He's still alive, no?
SI: Owen? Yes. He just published a new book on why we vote. Very intellectually engaged.
The other one, who's no longer living, I resisted more, but he got in my head in a way that over time, I realized was a huge influence, and that was Robert Bork, who was my con law teacher first semester.
MR: What was that like? Do you have any memories of him that really stick with you?
SI: Well, two things. One was he had just been Solicitor General of the United States when he came back to Yale and was my professor, and his approach to teaching was more close to his experience as a lieutenant in Korea, and it was daily combat. He would just basically throw a casebook on the table and say, "This is this case. You know what I think of it — who wants to take me on?" And the arrogance of first semester Yale Law students is unbounded and so we would, and he would rip everybody apart.
But what I really took away from that was he was the first person I ever heard ask the question: Who should decide? Not “What is normatively the best or right answer” in a Ronnie Dworkin sense, but what institutional arrangements should resolve this — especially if it's contested issues. And that has really been a grounding point for my entire career.
MR: One of the first things you said in our election law class was to ask whether the law should protect minorities. And everyone says, "Of course. We need to have special rules to protect minorities against the tyranny of the majority." And you said, "Great. What about billionaires?" And you went on to make the point that billionaires are minorities. And then people start scrambling.
Did you get that from him?
SI: Well, I think my mother would say I was born with that predilection to be contrarian. What I got from both Fiss and Bork was the importance of standing up against the priors of your students to forcing them to confront what they came in believing when they knew less about the subject matter. That's something that's become more difficult in the academy. We've gone through periods of intense student concern about their fragility and concerns about feeling intimidated or something of that sort. But I got that from both of them. I think that's the secret to good teaching. We talk about the Socratic method. I mean, you read Plato's account of the Socratic dialogues and there's nothing memorable that Socrates says in any of those dialogues. It's just the sense that everything opens up a question and leads to more searching.
From ’68 to Milei
MR: I joke with you a lot that you're a closet conservative. Have people ever said that about you?
SI: Oh, sure.
MR: Why do you think that is?
SI: Because I tend to have faith in markets. I tend to have faith in competition over choice. Where I depart from what I would call real conservatives is I see more areas of market failure than they might.
But I'm also distrustful of public power for a lot of public choice reasons. I think that one of the reasons that you responded to my courses is I'm thoroughly pluralistic in terms of where power should be allocated rather than concentrated. And I think that someone like yourself who hews to the libertarian impulses found that quite compatible. We had many discussions about this, as you know.
MR: Let me ask you this — when you're Obama's lawyer, for instance, do you feel out of place on the Left, especially on the professional upper-echelons of the Democratic world? Or do you feel you’re a voice that gets listened to?
SI: When I worked for Obama, I was one of his senior legal advisors. There were a half dozen of us and I thought pretty much that my role was to be a lawyer and not to try to direct policy. It’s a hard role for lawyers because they tend to be very expansive in their view of their role. I was probably among the more conservative people in that environment, but that was easy because, there, my role was to provide legal advice.
MR: I know you were a lefty in college.
SI: I started high school in 1968. My first day of high school was an occupation of the high school by people protesting against the teacher strike. I was 13 years old at the time.
New York in the late sixties, you grew up fast and I was too young for the whole SDS, which was on the college campuses. And afterwards the protests were over the Allende overthrow in Chile and things of that sort. But I went to law school and became a lawyer.
MR: Were there any books or people who influenced your switch from leftist to not?
SI: I think that when I was younger, I thought that you could have a comprehensive view of the world that should guide all conduct. But the history of the 20th century and just studying more made me very suspicious of complete ideologies. And one way of thinking about the history of the 20th century is as soon as somebody has a comprehensive ideology that covers everything and explains everything, you're probably best off just shooting them because nothing good is going to come from that.
MR: I know this is a complicated question but do you like Milei?
SI: So, had I been in Argentina for the vote, I would've voted for Milei, no question.
MR: Really?
SI: Oh, absolutely. In my lifetime, Argentina is one of the two countries in the world that has absolutely stagnated or gone backward in economic level, the other one being Zimbabwe. The answer to the question of why is Peronism. And Peronism is just the idea that you can make everybody dependent on the state, you keep giving away what you have in order to foster that dependence, and the country will somehow survive. And the secret to Argentina is that it hasn't. You walk through the streets of Buenos Aires and you see the magnificent echoes of a very wealthy past. In the 1920s, it was the fourth-wealthiest country in the world, and now you go there and 40% of the population is below the poverty line. It's terrible.
So when you have an election between the Minister of Finance who's running 140% inflation and decides that on the eve of the election, he'll suspend tax collection so that people feel wealthier, you can't vote for that. And Milei, we'll see what he can pull off. We'll see how much political authority he has. Already, the trade unions are mobilizing against him. He doesn't have a party, so he doesn't have a constituency in the congress. It's a very difficult role he has set about for himself. But he won big and certainly I would've voted for him.
Bad, Bad Sam Issacharoff
MR: Have people told you that you look like Jim Croce?
SI: When I had hair, I used to be told I looked like Billy Joel. And then I have an Italian friend who swears that I look like Paolo Conte, who's an Italian troubadour of the Leonard Cohen style.
MR: And also Bruce Pandolfini. He's a famous chess instructor.
SI: Him I don't know.
MR: So here's my question: Why do you have a mustache? How long have you had it?
SI: I've had it I think since college or something. I don't know the answer to why. It's sort of something that's natural in Argentina. All my cousins have mustaches down there. I don’t know.
MR: You speak fluent Spanish, correct?
SI: Yeah.
MR: Do you speak any other languages?
SI: I speak French. I used to speak it very well. I don't use it that much. It's rusty. And because I speak French and Spanish, I can bluff my way through in Italian or Portuguese.
MR: Your family's Jewish, right?
SI: Yes — we're from two different sides. My mother's family is Polish, Ukrainian, Russian, Belarusian, and whatever the mix of that area is — Jews from Eastern Europe who fled in the 1920s. My mother was born in Argentina to immigrant parents, a very common story there. My father's family is more complicated. They're from Samarkand in Uzbekistan. Then it was Afghanistan. My grandfather was born there, and my father was raised in Uruguay.
MR: So Bukharian, right?
SI: Yeah, absolutely. Bukharian Jews…very good. And you know Issachar, which is my family name, is one of the lost tribes, and the O-F-F is added in the late 19th century when it's conquered by Russia.
MR: Are you religious at all?
SI: No. I wasn't bar mitzvah-ed. My father wasn't bar mitzvah-ed. My mother has a grandfather who was a rabbi in the old country, but we're many generations removed from that.
MR: Do you believe in God?
SI: No. I don't have any religious impulses.
MR: Do you believe in an afterlife?
SI: I'd like to, but no.
A Class Act
MR: So you do a lot of work on constitutional matters around the world, including your new book, Democracy Unmoored. But you are also a giant in the world of class action and complex litigation but mostly defending class action agreements.
SI: I consult mostly with plaintiffs, but sometimes I'm brought in by both sides or by the court to help structure the agreement and then defend it on appeal.
MR: Who does your natural sympathies lie with? The defendant? The plaintiff? Or the court?
SI: I think that I'm deeply an institutionalist and I deeply believe in courts. Part of why I think why I've had some measure of success in this is because I do think about things institutionally.
But there's another side to it also, which is that usually the defense side of these fights has a lot of resources, and they have an organization already formed. Sometimes it's the government, sometimes it's a publicly traded corporation, and so they've overcome collective action problems either by the democratic process or by the process of being incorporated. On the other side, you have little people, and my sympathies tend to go to the little people, and they need a form of representation. You think about some of the cases I've been involved with, the Deepwater Horizon and the contamination of the Gulf, or the VW emission scandal, or the NFL concussion case, or now the opioids litigation — I tend to try to see myself providing the service to organize the other side of that collective battle.
MR: Do you enjoy writing briefs?
SI: Yes.
MR: What’s your process for writing?
SI: When I write briefs, I usually get pulled into a case that has been at some level advanced by other lawyers and I almost always appear on behalf of lawyers. So I like to work from somebody drafting some initial points with authorities and all that so I don't have to do the groundwork of putting in the cite and stuff like that. And then I just work and rewrite from that.
I take a lot of pride in appellate briefs, in the introduction that I write. Even though it's not formally called for in the rules, I spend a lot of time writing three to four pages as an introduction. And my view is if I can't win the case in those three to four pages, it's never going to happen. The remainder of the brief is filling that in and sustaining it with more citations and footnotes for refuting small points.
MR: And then what about for oral argument — how do you prep?
SI: For oral arguments, I spend time before the argument itself, just plotting through how I think it's going to go. And then I do two things before the oral argument that are a disciplining technique. The first is that I imagine, "How would I write the opinion that I'd lose in? What's the easiest way to write the opinion against me?" And so that's what I focus on in the immediate period before the argument.
And then I have a habit of, the night before the argument, I go out to dinner with the people I represent, and at some point I say, "Here's how I think the argument may go, and here are some of the issues that I think we're weak on. I would like your permission to give the following points away. That is, even though we make this argument, I want to give it up. I don't want to rest on it. I want to move beyond it as quickly as possible." That has the effect of making everybody part of the decision. And then I have in my back pocket concessions I may need to make at argument in case I do.
I think that courts respond well when it sounds like you're listening to what they're saying, and you engage with them. I've seen too many lawyers who get up and think their role is to dig in and fight on everything. My approach in court tends to be, I want to be a part of the process with the court. So I want to address the court as, "We have a collective problem. Obviously, I have clients, I want it to come out a certain way, but this is how I think it should play out."
The Best of the Bar
MR: If you could have one person represent you in court — it doesn't matter what it is, it could be criminal, antitrust, class action, civil rights — it could be anyone dead or alive.
SI: Well, I haven't heard many dead people argue.
But I think the best that I've been up against is Paul Clement. I mean, that's hardly a controversial statement, but one of the interesting things about his arguments is he doesn't try to overwhelm you with fancy language. If you listen to his argument, it's very plain-spoken. There's not the flowery, eloquent moment that you'll take away. It's just he engages plain and simple and he has a fierce memory so he knows the record backwards and forwards. And so when I go up against him, it's a challenge just to have that comprehensive a knowledge of the record and the law.
MR: If you could have clerked for any judge of all time, who would it have been?
SI: It probably would be somebody who was just a fierce, independent thinker way out of step with his time. I would think somebody like Holmes would come to mind, although I don't agree with many of his views. Certainly Harlan II would come to mind. I am a huge fan of the writing of Robert Jackson. I don't know that he was as consistently systematic a justice as Holmes and Harlan, but those are the ones that readily come to mind.
One more that may be unusual — Joseph Story — because he had a vision of law as part of creating the American Republic. That sustained him over this amazing career in which he was the main treatise writer and this incredibly important Supreme Court Justice and a pioneering professor at Harvard. That combination is just overwhelming.
MR: Did you ever want to be a judge?
SI: No, I didn't really. I like what I do. I like the classroom, I like the writing, I like the independence of it, and I like the advocacy role.
MR: Do you like money?
SI: Well, at this point I'm comfortable, so that's fine. But sure. I mean, I had kids, I had to put them through college and all that.
On the Court
MR: If someone said to you when you were 40 or 50, "Here's $10 million — go be a federal judge," would you have done it?
SI: I don't think so. It's not the role that I wanted.
MR: Interesting.
SI: The problem with being a judge, and I have many judges as friends and so on, is that it has to come to you and you're dependent upon what others bring to you. You can't create the world that you want to engage. Sure, you engage it with a lot of power and authority, but it is not the role that I saw for myself.
MR: You’re a big guy, do you ever play basketball?
SI: I used to play a lot of basketball.
MR: Did you ever play with Richard Epstein?
SI: Yes.
MR: Was he good?
SI: Actually, surprisingly so, yes. Richard's older than me. When we both came to NYU, we had a faculty game that one morning, I think it was Thursday mornings, that John Sexton would organize, and Richard had an ability that I've never seen in all my years playing basketball. He would come out there and he would tell the match-ups — it was a pickup game — and he would decide the match-ups for his team, who would guard whom, and then he would tell the other team what their match-ups were. It was so outlandish that we just kind of went along. "Okay, that's who we cover."
MR: What was John Sexton like as a basketball player?
SI: Very engaged. He was enthusiastic beyond his abilities.
MR: Michael McConnell clerked with him on the Supreme Court, and they would play and he said he was a trash talker.
SI: Always.
MR: Do you have any other hobbies?
SI: No, not really. It's one of the problems I have in thinking about what would life be like if I weren't doing what I'm doing, is there aren't really a lot of things. I work a lot. I write a lot. I teach.
MR: What do you do to unwind, for instance?
SI: To unwind? I do exercise. I have my bike. I ride my bike. I ride my Peloton when I'm in the country.
MR: What kind of bike do you have?
SI: I have a Bianchi, the original green and white color with electric gears and all that, and it's just too good a bike for me.
MR: It's a road bike?
SI: Yeah, a road bike. It's really a piece of engineering that's just beautiful. It's one of these things, you ride it, and you just can't believe how well-made it is.
MR: Are you a cosmopolitan guy? What's a vacation for you — going abroad or staying home?
SI: Going abroad. We have a country house in northwest Connecticut that sits on a lake and it's wonderfully peaceful. I swim across the lake and it's great.
Noisy Neighbor?
MR: Yeah. Do you watch any TV?
SI: Yes.
MR: What’s the last show you binge-watched?
SI: The last show we binge-watched was True Detective.
But our real preference at this point is the Swedish noir series The Bridge, which has an autistic woman as the chief detective and with gruesome murders, and that's just spectacular. I liked a French show called Engrenages. In English it’s called Spiral and it's the gritty side of Paris. It’s a French police detective style where each side has its code — the bad guys have their code and the good guys have theirs, and sometimes the code of the bad guys is better than the code of the good guys. I like that kind of moral ambiguity.
MR: What kind of music are you into?
SI: While I work, and this may be unusual, I like to listen to music, and I am a pretty big jazz fan, so I listen to jazz usually when I'm working.
MR: What kind of jazz? Who?
SI: I kind of like classic stuff. I like Miles Davis. I love the various ways that my neighbor performs, Ron Carter.
MR: He’s your neighbor?
SI: Yeah, he lives upstairs from me here.
MR: Really?
SI: Yeah.
MR: That's pretty cool.
SI: He's very cool.
MR: I interviewed Branford Marsalis.
SI: He's great.
MR: Not into the Grateful Dead?
SI: I listened to them when I was in college and I have problems with it now because it's too undisciplined for me. I like Bach, I like Philip Glass, I like Telemann. I like stuff that has a recognizable arithmetic or mathematical pattern.
MR: What Miles Davis do you like?
SI: I like the pre-Bitches Brew stuff. I like the Miles Davis Quintet, the So What period.
MR: Do you like bop?
SI: I like bop, but not quite as much. Categorization is always a problem, right? So I admire Charlie Parker, but I like John Coltrane better.
MR: Oh, that's the wrong answer.
SI: That's the wrong answer?
MR: Yeah, sorry. Thank you for playing, but that's the incorrect answer. You could like John Coltrane more than Miles Davis, I guess. That's an acceptable answer. It's probably not correct, but…
SI: Miles Davis — I really like the note that's not hit. So Thelonious Monk, Miles Davis —they take you to a point and then you know what's coming next, and then all of a sudden you don't because you're going in a different direction.
MR: What's the first song that comes to mind right now?
SI: Well, you asked about more modern things, so I was just thinking of Leonard Cohen, who I mentioned a minute ago. I'm a big fan.
MR: What song?
SI: Well, it's obviously, “Hallelujah.” That’s the great song.
MR: Dylan or Leonard Cohen?
SI: Of the two, to be honest, I prefer Leonard Cohen. But that's hard because Dylan has so much.
MR: Why do you preface it by saying "to be honest"? Do you think there's something embarrassing about liking Leonard Cohen? Do you think Dylan is more the correct answer?
SI: I think that Dylan's influence on contemporary culture is just so huge. Part of it is his longevity, part of it is just how many songs he put out. Part of it is that he wrote stuff that he didn't even record, gave to other people, that made it into sort of the canon of the period that I was growing up in.
But if you ask what I respond to, it's that the tragedy of life and yet looking for something in it that can keep you and sustain you. That sensibility I find more in Leonard Cohen than Dylan.
MR: What about jazz vocalists? Who does it for you?
SI: So, currently, I really like Cécile McLorin Salvant. Do you know her? I tend to like the French style.
MR: Do you like Jacques Brel?
SI: Yeah. More Edith Piaf and that tradition…including Carla Bruni.
MR: Do you like art?
SI: Some, yeah. We have a lot of art in our house.
MR: Is there an artist that you love?
SI: The artists that I love are people who I can't afford to collect. Cezanne. Some of the Impressionists. I'm a big fan of Georges de La Tour. De La Tour is a Flemish painter in the late Renaissance, when you started to get real comfort with the human body and so forth.
MR: He's the chiaroscuro guy?
SI: Yes. He’d so hands over the candles, they're trying to figure out the anatomy and all this. There's a couple of his paintings that I saw in the Louvre when I was young and that just kind of blew me away.