Jeffrey Toobin: ‘Supreme’ Writer

If there’s a legal issue of national significance—relating to the U.S. Supreme Court in particular—there’s a good chance Jeffrey Toobin is on the scene. Whether it be via feature article for The New Yorker or a bit of television analysis for CNN, Toobin is hardly just another talking head. Unlike many TV legal analysts, Toobin spent several years practicing law before becoming a full-time journalist and author.

His fifth book, <emThe Nine, took an inside look at the justices behind the highest court in the land. The book received widespread praise, and his reporting has helped put him in an ideal position to break a good deal of the news surrounding Justice David Souter’s decision to retire from the court and Judge Sonia Sotomayor’s nomination to fill his seat.

Name and current title?

Jeffrey Toobin: Staff writer, The New Yorker; senior analyst, CNN; author.

Law school?

Harvard Law School. Class of 1986.

Before becoming a full-time journalist, you practiced law. What did you do?

I was a law clerk then a federal prosecutor for about six years—first as a junior lawyer with the Office of Independent Counsel under Lawrence Walsh, then as an assistant U.S. Attorney in Brooklyn.

What was your worst moment as a lawyer?

My worst moment was probably my first solo trial, an acquittal on all counts.

What was your best moment?

My best moment was probably my last trial, when I won a conviction against a corrupt personal injury lawyer, after his first trial ended in a hung jury.

You’ve worked for ABC and CNN. How did you get into TV journalism?

The short answer is OJ. I was covering the Simpson case for The New Yorker, and the networks started looking for people who understood how criminal trials worked. (The job of television legal analyst did not yet exist.) So I started being called by TV Folks who were covering the case.

Admit it—isn’t being a pundit more fun than practicing law?

I really think of myself more as a journalist than a “pundit.” I have opinions, probably more than most straight reporters, but I try to ground them in actual reporting. I certainly don’t consider myself a partisan. And yes, it’s fun.

You received an Emmy in 2000 for your coverage of the Elián González custody battle. Did that change your career? Do Emmy’s matter?

The Emmy did not change anything. It was nice to win, and it’s nice to display, but I don’t think it had much impact on my career.

What was the moment when you said, “I’ve got to get the f*** out of law?”

I never said I had to get out of practicing law. Three years into my tenure as an AUSA, Tina Brown took over as editor of The New Yorker. David Remnick, then a young staff writer at the magazine and a friend of mine, suggested I submit my clips for a job. Forty-eight hours later, my legal career was over. It was more a lark than an escape.

You were an editor of Harvard Law Review. Does that make you a big man on campus at Harvard Law, or do people only end up gunning for you more?

I was not a big man on the Harvard campus. Most people had no idea who was on Law Review and who wasn’t. It’s a place full of self-confident people; they mostly didn’t care much (pro or con) about their classmates.

You cut your teeth as a lawyer during the Iran-Contra scandal and subsequent Oliver North hearings. There’s a long history of historic and contentious Congressional investigations, but these days (with the possible exception of recent bank hearings), the idea of an explosive Congressional investigation seems almost quaint. Are we post-hearing in the U.S.?

I’m certain there will be dramatic Congressional hearings in our future. For one thing, members of Congress are too addicted to the publicity. Long-running serials, like Watergate and Iran-Contra are rare, but I had the privilege (and fun) of covering the House impeachment hearings for President Clinton—and I expect there will be more in that vein in the future. (Though, for the record, I doubt President Obama will be impeached or get into that, uh, kind of trouble.)

In your latest book, The Nine, you take an inside look at the Supreme Court. Few reporters get the kind of access you did. What was the most surprising thing you learned?

I guess I knew in an abstract way that the Justices were ordinary people, with strong political views, but I certainly didn’t know the details until I started reporting The Nine. Specifically, the personal and political odyssey of Sandra Day O’Connor was my favorite part of the book.

Name three jurists who should have been on the President’s radar but, for whatever reason, would’ve never made the shortlist?

David Tatel, Judge, D.C. Circuit (too old); Laurence Tribe, Harvard Law professor (also too old); me (can’t be confirmed; unqualified).

You began your journalism career as a freelancer for The New Republic while you were in law school. Did you find Harvard boring or something?


Seriously, though, what was your first pitch? How did you break in?

I loved the first year of law school, but I got restless and even a little more so in the second year. That’s when I started freelancing for The New Republic. I looked for legal stories I thought I could make interesting for a general reader. That’s still what I do, all these years later.

In BigLaw, there’s been more talk lately of alternative billing models and the possible death of the billable hour. Meanwhile, in journalism, it looks like the sky is falling. What will journalism and BigLaw look like as we begin to rebuild our economy?

I’m more confident about the future of BigLaw than I am of big (or biggish) journalism, especially newspapers. Lawyers can always, more or less, create demand for their services, but we can’t force people to read, watch or buy that which they don’t want to read, watch or buy.

We read a lot legal news here at Bitter Lawyer. One thing we’ve noticed is that journalism has become an endless series of “hat tips,” with reporters and bloggers incessantly attributing news around to each other. Do you ever feel like the Internet is just one big feedback loop with no fresh content out there?

I love blogs and do some blogging myself, but my main complaint about the field is the dearth of original reporting and surfeit of . . . opinion. Real journalism—the seeking of facts and information—is the grist for most blogging, and I think it’s important that the financial incentives continue to exist for people who search out the news. It’s expensive and time consuming, and bloggers (who are mostly unpaid) are not in a position to do it in a sustained way.

You’ve written five books, can you tell us what you’re working on next?

No new book. Looking for a good subject for one. [Since this interview he has written a new book, The Oath: The Obama White House v. the Supreme Court, expected to be published in September 2012.]

Any advice for lawyers out there looking to start a new career?

My only advice is to try to do what you love. And be lucky. I drifted from law into legal journalism just before a boom in that field, but I never could have predicted what would happen. Enthusiasm is more important than just about anything.

  • Anonymous

    Cool guy. More down to earth than I thought he’d be.

  • Anonymous

    How funny, I actually watched him on CNN yesterday.  Supreme Court Justices sort of freak me out.  They’re not quite real people.

  • RC

    @9:30:  great point.  i think the same thing.  they wear robes at those state of the union addresses… i always wonder if they think it’s a little silly.

  • Anonymous

    @ RC,
    The robes are little silly. Kind of like baseball managers wearing uniforms. What’s with that? Except this is kind of like Joe Torre walking into a bar wearing his uniform. Wish they would just wear suits when not on the bench.

  • George22

    I always see him on CNN. He sounds like a cool dude.

  • BL1Y

    @RC: I think it makes sense for them to wear the judicial uniform for the State of the Union.  They are present as justices, just as the joint chiefs show up in uniform because they’re there in their capacity as military officers.  If it was the press corps dinner, I’d expect to see both groups in tuxes.

  • Anonymous

    Oh BL1Y,
    Can you ever just agree with anyone?

  • Anonymous

    comments about robes and joe torre in baseball uniform are brilliant.  love it.  this bl1y guy seems a bit obvious and hyper-literal, no?  oh, wait, he’s a first year associate.  that’s his job.  to be literal dude. hey bl1y, perhaps you should just sit this dance out?

  • Anonymous

    I wonder what these people wear under those robes?

  • Anonymous

    Perish the thought!  Somehow thinking about Ruth Bader Ginsburg and this new woman and what’s underneath the robes is enough to make us think of having them wear Burakaz!

  • Anonymous

    What kind of butt-wipe is daman?

  • Anonymous

    you’re a tool.

  • JJ

    Great interview.  I’ve always liked this guy.

  • Steve

    Interviews are my favorite part of this site.  How do you guys get such big names?

  • Allison

    I agree with Steve.  LOVE the interviews. Need to talk to some interesting women though.

  • ANon

    I was always curious about this guy – thanks for the good interview.

  • mike

    Toobin looks like a typical liberal idiot, after his comments during the Weiner incident, and what Toobin said about Breitbart. Regardless of what you think about Breitbart – he got the story right all along, and Toobin had it wrong. Dead wrong. Maybe that’s because Toobin in his life seems to have real issues with the truth regarding his own sexual activity. Not exactly the “expert” that I would put on CNN for qualified opinions about Weiner!

    Like I say…”typical”.