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The Man Who Explains O.J., the Supreme Court, and Donald Trump

How Jeffrey Toobin — author, ‘New Yorker’ journalist, CNN legal expert, and prestige-TV muse — makes sense of an increasingly senseless United States of America

When Jeffrey Toobin walks into the lobby of CNN’s New York City headquarters, he’s alert. He has to be, given the state of things, and his role in helping us understand those things.

Lately, it’s felt as if Toobin is everywhere. He has to be. In The New Yorker, where he’s been on staff since 1993, he writes about everything from the death penalty to Clarence Thomas to Hulk Hogan and Gawker; this week, he published a profile of Leonard Leo, the executive vice president of the Federalist Society, whom Toobin credits with anointing one-third of the current crop of Supreme Court justices. He has near-daily appearances on CNN, where he’s been the network’s senior legal analyst since 2002, to weigh in on the legal matters du jour. Elsewhere on television, it was his book, 1996’s The Run of His Life: The People v. O.J. Simpson, that served as source material for last year’s American Crime Story series on FX, which picked up nine Emmys in September. American Crime Story has since optioned Toobin’s 2000 book on the Monica Lewinsky scandal, A Vast Conspiracy: The Real Story of the Sex Scandal That Nearly Brought Down a President, for the show’s planned fourth season. Meanwhile, the writing team from the first season has developed a screenplay for a feature-film adaptation of Toobin’s seventh and latest book, American Heiress: The Wild Saga of the Kidnapping, Crimes and Trial of Patty Hearst, which was released in paperback this month.

Somewhere along the way, he became America’s go-to legal expert. Want to know what to make of Donald Trump nominating Neil Gorsuch? What’s the precedent for Barack Obama’s executive actions? What about the way the Supreme Court makes itself accessible to the media and public? There’s Toobin on national TV, calmly parsing the intricacies of our legal system. On Twitter, he’s been known to tease critics and have some fun at his own expense.

Recently, when a follower tweeted at him that he admired Toobin’s legal perspectives and wished he were his lawyer, the writer fired back. "Thanks, but don’t get carried away," he wrote. "I just play one on tv."

That’s not exactly true: Before Toobin was a journalist, author, prestige-TV muse, and news-network talking head, he was, in fact, a lawyer. I spent an afternoon with him, to ask about how he went from federal prosecutor to legal soothsayer of the people, what’s inspiring the boom of crime-of-the-century stories on television, why we can’t stop talking about O.J. Simpson after all this time, and how to approach big stories in the time of Trump.

You went to law school and then you became an assistant U.S. attorney. How, and why, did you make the jump from law to journalism?

As my father used to say, to make a long story unbearable: My parents were journalists. My mother [former ABC and CBS correspondent Marlene Sanders] was one of the pioneering women television correspondents. My dad [Jerome Toobin, the longtime producer of Bill Moyers] was one of the founding fathers of public television. I grew up hearing about journalism at the dinner table, but I also grew up hearing about how difficult and unpredictable it was. And my parents’ explicit advice to me was to go to law school, be a lawyer, be a prosecutor, run for office, and do something different from them. And that was where I was headed.

But throughout my childhood and young adulthood I also wrote for the school paper, and I was sports editor and editorial chairman of The Harvard Crimson. I started freelancing when I was in law school. I guess I feel like I came into my genetic destiny. Right out of my clerkship I worked on the [Iran-Contra] Oliver North case, and I decided to write a book about that, which I did — my first book, Opening Arguments. But I thought it was kind of a one-off thing.

Then Tina Brown got hired at The New Yorker right when I was looking to leave the U.S. attorney’s office, and they were looking for people to write "Talk of the Town" stories. I thought, what the hell, I’ll try it. I did it for a year, and then a year later the O.J. Simpson case happened, which really put me on the map as a journalist. It all sounds more planned out and orderly than it actually was.

Was the plan always to write about politics and the law?

Not at all. The plan was to veer toward politics: to run for office, to work in the government. I always thought of writing as a sideline. But I was fortunate — I managed to make it my full-time job. And for a journalist, hitching yourself to a huge story has always been a route to success, and certainly that’s what O.J. was for me.

When you started appearing on TV, was that specifically in conjunction with the O.J. trial?

People don’t realize that the institution of the television legal analyst did not exist until the O.J. Simpson case. And many of us who still do it, like Cynthia McFadden, Dan Abrams, and Greta Van Susteren — all of us sort of got our start with O.J. I started doing TV for free during O.J. because I wanted to get known and I wanted sources to cooperate with me, and I just thought it was fun. And then once the O.J. civil case happened and my book came out, it became clear that there was an opportunity to be employed as well as just appear on television. So in 1996, I signed with ABC to be their legal analyst, and I did that for six years. And I moved to CNN in 2002.

Was there a moment that you felt like you shifted from being an O.J. Simpson expert to being a sort of jack-of-all-trades legal expert?

I’ve always thought my job, both in print and on television, was to translate legalese into English. I assumed that once the O.J. Simpson case wound down, interest in me as television performer would wind down as well. But what I didn’t realize was that the O.J. trial created its own demand among viewers for explanation of what was going on, and while there’s never been a case as big as O.J., there has been a steady diet of important and interesting legal issues that I have been covering for the past 20 years.

You’re on TV just about every day at this point. Do you get recognized on the street?

You know, it’s funny. The culture of New York City, where I live most of the time, is that people almost never say anything. But it happens all the time elsewhere. I’m big in airports. But it’s very strange — I spend most of my time in New York, and the number of times people say something to me on the street is really very small. Yet, as soon as I leave, it starts happening all the time. It’s a very interesting cultural difference.

When people do approach you, is it because they recognize you from CNN? Or do you get more specific responses to the stories you’ve worked on?

For a long time, people would say to me, "Oh, you’re that O.J. guy." But that hasn’t been true for a number of years. People have moved on. I think I’m recognized as a guy who talks about law on TV.

(CNN)
(CNN)

For years, an older African American woman worked at the polling station near my home. And every time I would go to vote, she would look at me and she would say, "You know, you were unfair to O.J." And she would say it every Election Day. It was interesting, because it was just sort of funny, but she was also the perfect demographic for believing in O.J.’s innocence. All the surveys and research on both sides said older, African American women were most sympathetic to O.J. And she completely bore that out. [Toobin wrote about the prosecution’s research on this subject in a 1996 story in The New Yorker.] Long after anyone else was talking about it, this woman still had an ax to grind.

Do you feel less like an interpreter of legal issues when you write?

I kind of have a hierarchy in my mind. I used to think that my role on TV was to be very much a neutral explainer. In The New Yorker I allowed myself a greater voice, a more opinionated voice. And in books, I felt almost obligated to take clear stands on issues because I think people expect if you’ve written a book on a subject you should have some opinions. I think television has changed in that we’re expected to have more of a voice than we once did. So that distinction among the three outlets is less clear than it once was.

So you’re almost in the position of being a pundit?

I really just hate that word. I don’t even know what it means, exactly. CNN hires people who are Democratic strategists or Republican strategists, but that is very much not my role or my interest. That is not to say that I have no opinions, but it’s just not the way I like to express myself.

How do you choose stories to cover?

I think choosing stories is the hardest thing I do. I feel like once I’m on a good story I know exactly what to do — I know how to report it, I know how to write it. We live in a world where all good news outlets are becoming more magazine-y, so if there’s a good New Yorker sort of story out there, The New York Times may be doing it, New York magazine may be doing it, The Washington Post, Vanity Fair. And I’m competitive, so not only do I want to be the best, I want to be first. So finding something that is big, but mine, is the challenge that I have.

With your books, are you explicitly setting out to write the definitive history of X?

Not really. I’m very conscious in terms of books of just wanting to write something that people would want to read. I am deeply aware of the number of distractions that are available in modern life — I mean, I’m on my phone as much as anybody else. It’s a challenge to get people to sit down and read a book. So I am much more concerned about being interesting than I am about being definitive. Now, obviously if you’re going to go to the trouble of trying to write a book, you’re not going to try to write a half-assed book. And certainly, with Patty Hearst, no one had written about this in a journalistic way for 30 years — and frankly I don’t expect people will again having seen my book. So in that respect, I wanted to tell the whole story.

The adaptation — or adaptations plural, since there are two more coming — of your books have come in this boom of anthology series on TV. American Crime Story is going to look at Hurricane Katrina (Season 2) and then the assassination of Gianni Versace (Season 3). There are separate projects focusing on the Branch Davidians in Waco and the Menendez brothers. There’s been a recent explosion of not just true crime stories, but crimes that really captured the popular imagination. Why do you think that’s happening now?

I think there are a variety of factors. One is that we are in a kind of golden age of television. You have a period now where the best actors, writers, and directors want to work in television after a hundred years when they all wanted to work in feature films. I think crime is also an enduringly fascinating subject that raises all the big issues at a macro level, but there are also juicy, fascinating, gory, interesting stories.

Tina Brown always used to talk about high and low: You want stories that are about serious issues, but you also want juicy, down-low stories. And O.J. was really just the perfect combination of the two. It’s also just Hollywood being Hollywood: People imitate success. And O.J. was successful, so they figured, let’s do more of that.

How did you get involved with FX?

That was complete random fortune. I wrote The Run of His Life in 1996 — a long time ago. And I had many conversations with people about [adapting] O.J. And the thing you heard over and over again was: People know the whole story and people are sick of it. I felt strongly that neither of those things was true, but what difference did it make what I thought? I wasn’t the person writing the checks.

Toobin’s character on ‘American Crime Story’ (FX)
Toobin’s character on ‘American Crime Story’ (FX)

I got a call from Brad Simpson, who is partners with Nina Jacobson in a company called Color Force, who said we want to buy the book and we want to work with [showrunner] Ryan Murphy on a miniseries. But it’s not like I did anything to encourage them. I don’t want to give myself any sort of credit. The one thing I will take some credit for is when they set out, they wanted to look at O.J., and they said, "What’s the definitive book?" And I do think, without false modesty, I have the best O.J. book.

Some of the characters portrayed in the O.J. series have spoken about watching it. Marcia Clark, for example, talked about watching every week while it was airing. Do you know if O.J. has seen it?

I don’t. My sense is no, because FX is premium cable and I don’t think they have that in prison in Nevada. So I don’t think so. One of the weird aspects of my career is that I have never met O.J. Simpson. I’ve never interviewed him, we’ve never even had a conversation. I’ve written to him quite a few times since he’s been in prison, and he hasn’t responded. You know, it’s interesting — I don’t think he’s responded to anyone since he has been in prison in Nevada.

Do you get the sense he knows how much attention the American Crime Story series got?

The only thing I know in that regard is in this weird 2016 Year of O.J., there was also Ezra Edelman’s ESPN project, which I thought was absolutely brilliant. It opens with video of some sort of hearing, and it’s the first time I’ve seen video of O.J. since he’s been locked up in Nevada. You can see he’s really aged. I mean, prison is rough. Even not the worst prison is still a bad place to be. O.J.’s also pushing 70 now, so it’s rough for him to be in prison. And you can see how physically diminished he is — he’s very overweight and very gray, and he looks pretty awful. But that’s all I know about his life in prison.

There were rumors that he didn’t like the casting of Cuba Gooding Jr. to play him.

You know what? That’s too bad, O.J. I don’t know what to say. It wasn’t up to him. I’m sure there are a lot of things he doesn’t like, starting with the fact that he’s in prison.

A lot of your writing about O.J. — both in your reporting and in your book — mentioned how unique his trial was, and that what made it so explosive was all these different elements coming together at the right time. Why does the case still resonate so strongly?

The line I have always used about it is that it’s a story that combines everything that obsesses the American people: It had sex, it had race, it had violence, it had sports, it had Hollywood. The only eyewitness was a dog. So it really was this perfect compilation of things.

What I was especially pleased with about the FX series is that, while it was very much its own adaptation of my work, the theme of my book was race. That was certainly the theme of the FX series as well. And there’s no bigger, more enduring story in American life than race.

Another reason why I think the series touched such a responsive chord is that, purely by chance, it ran in the more or less immediate aftermath of Ferguson and Black Lives Matter, a story where relations between African American suspects and white cops was at the heart. It just felt relevant again.

It seems like you identified that race would be the issue in the trial very early on.

Well, you have to remember that the whole reason I am identified with this story is that I wrote this piece about Mark Fuhrman and the plan to blame him for planting the glove very soon after the murders. And Episode 3 of American Crime Story is very much about my New Yorker story, and there’s an actor who plays me. So I was linked to the racial part of the story very early on. It also happens that in addition to being a crime reporter, I am also someone who’s very interested in the Constitution and the Supreme Court and these bigger issues in American history. So it was especially interesting to me to view this case through the prism of race rather than other ways you could look at it, like celebrity.

What was it like seeing yourself played by an actor?

That was so crazy. I happened to be on the set when Chris Conner, the actor playing me, did his big scenes with [John] Travolta, and it was one of the more bizarre experiences of my life. Including weird stuff, like in writing my book I had never really described [Robert] Shapiro’s office. It didn’t seem all that relevant. But one of the things I remembered was there was this spiral staircase leading right up to his door. The set just by coincidence had this spiral staircase that looked exactly like the real one — like wow, that’s a karmic, bizarre element.

I watched the scenes between Travolta and Chris — that is, Shapiro and me — and I remember thinking, "Well, this was 20 years ago, and I don’t remember exactly word for word what happened." But it did seem pretty darn accurate. I was a pretty new reporter at The New Yorker when all this happened, and it mostly took place in Los Angeles. And the idea that 20-plus years later this would be acted out on film with John Travolta? The surreal aspect of it hit home.

Did Chris Conner study your mannerisms for the role?

I don’t think so. Although he did kind of look like a younger version of me. Fortunately, he was better looking, so I’m preserved in posterity. But I think they nerded him up a little — he had a corduroy jacket, and I’m not so much a corduroy-jacket kind of guy. But one of the things I did do is — I’ve carried the same size of reporter’s notebooks my whole career. I always have one with me in my bag just in case something comes up. And as they were shooting, I gave my current one to Chris. So he had an authentic Jeffrey Toobin notebook with him.

You have a knack for finding spectacular moments in politics and culture. I’m curious what you think about writing in the time of the Donald Trump administration, when rarely a day goes by without some sort of spectacle.

David Remnick, the editor of The New Yorker and my boss, one of the things he likes to talk about is he wants to hear big, dumb ideas. I think a lot of us at The New Yorker and in the magazine world — we’re always looking for the clever, untold, behind-the-scenes story. And David is always saying, "No, no, tell us the big story. Tell us what’s really important."

(Getty Images)
(Getty Images)

Trump’s obviously this giant story that is not just about politics. It’s also about culture, it’s about personality, it’s about wealth, it’s about economics. It is such a big story. He is such a big story. But it’s so much in progress. One of the things about bigger projects is you want to have some sort of arc to the story. My recount book [about the 2000 presidential election], Too Close to Call, was 36 days: How did the recount happen? You start with the incredibly close election and you end with [Al] Gore’s concession. It’s a pretty clear narrative arc. O.J.: You start with the murder; you end with the acquittal.

What’s the Trump arc? I have no idea. I have literally no idea. There are people who will tell you that this presidency cannot go more than six months: He’s too extreme, he’s too crazy, he’s too corrupt, and it’s just going to all fall apart. There are other people who will say, and I tend to put myself in this camp, that you know, most presidents get reelected, and it’s very possible he’ll be president for eight years. In light of those incredibly different scenarios, I feel like I have no handle on Trump as a subject. And, at least at this point, really have no sense of what kind of book you would want to write about him. God knows there are going to be a lot of Trump books, and certainly you could write a book about the campaign — I assume John Heilemann and Mark Halperin will write that book again, and they do a great job. But it’s not my thing. Someone said "Well, why don’t you do All the President’s Men about the Russia investigation?" What if the Russia investigation goes nowhere? I just feel like we are so early in the Trump story that I don’t see it as a book, at least for me, yet.

Are there unique challenges to covering politics in the Trump era?

Oh my God, Trump is like no politician I’ve ever covered. He’s like no president I’ve ever covered. I have felt almost literally a sense of vertigo in terms of covering him — the way he expresses himself, the incredibly chaotic and unfamiliar way he acts, the way he attacks people. I think regardless of party, we had, or at least I had, a concept of how presidents behave, and that’s completely out the window. It’s not just the tweeting. It’s the way he talks and the way he behaves and the kind of White House he runs. It’s just like nothing I’ve ever seen.

Do you find yourself logging certain moments that might turn into something?

Not in any sort of orderly way. One of the good things about working at CNN is that, because I’m on the air at least some every single day, I do sort of have a sense of what the big stories of the day are. The job doesn’t give me the chance to check out.

Jeffrey Toobin and Barry Scheck at the New Yorker Festival in 2011. (Getty Images for The New Yorker)
Jeffrey Toobin and Barry Scheck at the New Yorker Festival in 2011. (Getty Images for The New Yorker)

I think one of the lessons of the whole Trump story is how wrong people like me have been about what’s a big story. You remember during the campaign: Oh, Donald Trump said about John McCain that prisoners aren’t war heroes, "I like people who weren’t captured." Oh, it’s the end of his campaign. He said Megyn Kelly is bleeding from "her whatever" — now it’s the end of his campaign. He said terrible things about a Gold Star family — oh, he’ll never recover. Access Hollywood, sexual assault — oh, that’s it. So I am especially skeptical of my own judgments about what’s a turning point and what’s not. I really think Donald Trump should provoke a lot of journalistic humility. I certainly feel it.

How do you begin to look for the big story with Trump?

I think there are ways to look at the story. Like for example, one way to look at Donald Trump is through his businesses, and show how he made his money and show where he did well, where he did poorly, and how are those experiences reflected in his worldview. Another way of thinking about Trump is through the prism of gender: the way he has interacted with women throughout his life, the way he talks about women, and how that played out in the course of his campaign.

One of my early mentors in journalism, Fred Dannen, who was a magazine writer — I came up with some idea for a New Yorker article, and he said that’s a subject, not a story. Donald Trump is a subject.

Does the way the Trump administration handles facts change how you try to approach things, especially on TV? How do you reconcile that?

I think it’s been an adjustment. There’s been an evolution. It’s important to remember that the culture of CNN, certainly, was a very firm belief in balance: If one politician said the sky is blue, you would give the other party time to refute that. We have adopted the word "false" in our journalism much more thanks to Trump, because he’s said so many things that are just not true. We are now experimenting with the word "lie." Now, "false" is easier to establish than "lie." If Donald Trump says his inauguration crowd was the biggest ever, I have no problem saying that is false. But is he lying? What’s his intent? Mainstream journalism, at least in the form I’m most familiar with, which is CNN, has really evolved in terms of taking clear stands about what’s true or false. It’s not balance to let someone say something that’s just not true.

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