Interview: Benjamin Wittes // May 8, 2018

Benjamin Wittes is the editor-in-chief of Lawfare, a widely read national security blog, and a Senior Fellow in Governance Studies at the Brookings Institution. He speaks frequently about detention, interrogation, and national security issues. You may also be familiar with his Twitter account. After huge news stories break, he posts videos of his baby cannon blowing things up. I’m delighted that he took the time to talk with me. 

When you were in high school, what were you interested in? Were you already into journalism and national security?

No. Not at all. I played the french horn; I was pretty serious about that. I kind of knew I wanted to write, but I did not have a particularly refined sense of my interests substantively. I had an interest in history, but it was pretty diffuse. Yeah. My interests in this area came later.

Did you have any important teachers or role models when you were a high school student?

I was a terrible student. I hated school. I had many important role models; they did not tend to be school figures. And you know, I am the rare person in my field who never went to law school and has no advanced degree of any kind. That’s partly a function of the fact that I didn’t like school very much. You know, I almost didn’t finish high school. And then, when I went to college, I kind of figured out that if I didn’t do it very quickly, I wasn’t going to finish it at all. So I did college very, very fast. When I left, I kind of swore a blood oath that I would never be a student again. And I have lived with that ever since.

Oberlin is an excellent school, but is part of the reason that you went there because it’s a freethinking place where you could explore different interests without having it set in stone?

Yes and no. So the real reason I went there is that I got in. I was a poor enough student, and almost all colleges were easier to get in then than they are now. Oberlin is a quite selective institution, but it was much easier to get into then than it is now, and it was the school that I got into. Or one of a very small number; the other was also a small liberal arts college that had relatively liberal admissions policies.

In addition, I went to Oberlin because I was a pretty serious musician, and there’s a really excellent conservatory of music there. And that turned out to be irrelevant to the rest of my life, because I had a bad facial injury in the summer of my senior year. I had surgery on my jaw, and I never really played horn seriously again after that. So I went to Oberlin for reasons that have very little to do with anything except — I mean, I’m very glad I went there, because among other things, I met my wife there, and we’ve been married ever since. And I, in many ways got a very good education there, and I’m fond of the place in a weird sort of way. But it had very little to do with who I am professionally.

I’m also interested in how it affected you politically. Because Oberlin has a reputation for being very, very liberal, but you aren’t a hardcore leftist. You didn’t become a neo-conservative either. So how did you develop your “contrarian-centrism” there?

So, when you go to a place like Oberlin, you have four choices politically. One is you can drink the political Kool-Aid and become part of the political culture of the place, which was then as now, hard left, politically correct, and quite oppressive.

The second option is that you can become a reactionary conservative, kind of in response. So one of my classmates was Michelle Malkin, who graces Fox News with her right-wing fever swamp anger.

One possibility, and I think a lot of people chose this, is what you might call quietism. Right? You just opt out of the political discussion entirely. So this was most true of the people in the conservatory. They were just like, “I’m a conscientious objector from this, I’m just going to sing.” [laughs] “I’m going to do my thing, and I’m going to pretend none of this is happening.”

And then there is a group of people who have — and I was one of them — who kind of have a different attitude. My reaction was to say, “I am not going to let the atmosphere of this place define my political views in any way.” I’m not going to do it in reaction to it, I’m not going to accede to the political climate, but I’m also not going to define my politics in opposition to the political climate here. I’m just going to insist on my sovereign authority as a human being an an independent mind to make up my own mind about things. I think that’s the fundamental impact that Oberlin’s political climate had on me — a sense of “fuck you, you don’t get to determine how I think politically: either by dominating my brain and bullying me, or by making me a reactionary in response to the attempt, or by forcing me out of the conversation.” And a kind of fierce insistence on independence. That’s what I took away, although I would never have been able to articulate it at the time.

It’s cool that you took a positive away from that experience. Because college is the time when most people discover themselves politically, while you felt like you had to keep it to yourself.

Well, I didn’t keep it to myself! But there were a number of known paths, and I did refuse them. Now, whether my own path was a form of reactionaryism — it may be. [laughs] So I don’t want to say that my way was right. But it was what I did.

After you graduated, you started writing for the Legal Times (which sounds like a dream job out of college). What kind of stories did you report on there?

So first of all, there was a period of time between Oberlin and Legal Times. And I think particularly, for somebody like you, it’s probably worth dwelling a little bit on that period of time. I came out of school having no freaking idea what I wanted to do with myself, other than than I knew that I wanted to write and I didn’t want to go to grad school. That’s kind of all I knew. So when I left Oberlin, I took a bicycle and I put it on an airplane. And I flew to New Zealand, which is about the farthest place that it’s possible in the world to be from Oberlin, Ohio or the east coast of the United States. I spent a number of months riding around New Zealand on a bicycle.

When I came back, I did two things. One is I got engaged. The second is that I started looking for a job. I spent three years kind of trying to write stuff, and I thought I wanted to write fiction. It took me a little while to figure out I was terrible at writing fiction. That’s something you don’t actually figure out until you try it for a while. And the reason I was terrible at writing fiction was interesting; it was that I have no imagination at all. That’s not something that people often say about themselves, because they’re ashamed of it or something. And I’m not ashamed of it. I’m just not an imaginative person. I’m kind of intellectually imaginative, but making up stories? Just not good at that. Making up characters? Not good at that. So that makes it pretty hard to write novels. We have this idea when you’re a teenager or early twenty-something that if you’re a good writer, that means you can make stuff up. Those are actually completely separate skills. There are highly imaginative people who cannot write, and there are people who write gorgeously who couldn’t make up a story if you put them on a desert island with nothing but a pad of paper and a pen. So what I found as I tried to do this for a few years was that I had nothing fiction-wise to say that anybody wanted to read — even that I wanted to show anybody to read. But whenever I would kind of try to write something that was true, I could publish it.

And I found something else, which was interesting. I lived in Washington, since it’s kind of where I’m from. There are all these public record rooms in Washington — you know, government offices and shit. I would go into these offices, and I would walk out with stories that other people didn’t notice. Because I was good at that. Just good at figuring out what’s important in a pile of information. And what I found was that I was a pretty natural analytic reporter and a really bad fiction writer. What I learned from that — what really moved me in that conversation with myself — was that, you know, the market is sending you a signal here. The market is telling you what it wants from you, what the world actually thinks is valuable in you. And the question is, do you listen to that?

My interest in law came later. So, in a relatively short period of time after that, I had my staff job at Legal Times. That was an incredible group of people who worked with me. They all went on to do amazing things. Danny Klaidman, Naftali Bendavid, Eva Rodriguez, Tom Watson, Carrie Johnson — who’s now the Justice Department reporter for NPR — it’s an amazing group of people. Stuart Taylor. It was a really, really strong group, and I learned a huge amount from them.  

They were all fundamentally political reporters and institutional reporters, and I was a law nerd. And that meant that they got all kinds of stories that I didn’t get, and I read all kinds of things that they didn’t read. And I learned a shitload of law. So they went on to be great reporters, and I went on to be a legal analyst at the Washington Post and then here. And if you had met us all at Legal Times and said, “Who’s going to be the great investigative reporter here?” you would have said Danny Kleidman, and that’s exactly what happened. And if you’d said, “Who’s going to be the great beat reporter here,” you would have said Carrie Johnson.

But that place gave us all a lot of opportunities to kind of define who we were, and for me a lot of the definition was actually that I was substantively interested in the legal areas that we were looking at. I wasn’t as interested in what the political or institutional story you could tell was; I was really interested in what the substantive arguments that were being made looked like.

What did you learn from your editors at the Legal Times about what to do and what not to do in the editorial role?

Journalism is one of the last true apprenticeship professions. There’s no license. To be a lawyer, you have to join the bar. In almost all states, that means you have to go to law school. So there’s a formal training. To be a dentist, you have to get a license to practice dentistry, and that means you have to go to dental school. To be a massage therapist, right, there’s some training associated with it and a license in most jurisdictions. To be an accountant… you can play this out over a lot of fields.

To be a journalist, you have to do journalism. That is the only definition of a journalist. There is no license, there is no formal credential, there is nobody who will ever put their hands on your head and pour olive oil on your head and say, “I anoint you journalist.” It just doesn’t happen that way. You start doing it and you become it because you do it. And that puts a very heavy premium on the training you receive at the hands of others who are doing it. I was very blessed by working first at Legal Times and then at the Post with really superlative individuals. The process by which I learned journalism was the iterative process of writing and being edited and being sent back for more information. And doing it again. And then doing it again every day. There’s nothing like writing an editorial every day for ten years, which is basically what I did. Actually, nine years, and it wasn’t quite every day — but I wrote a lot of editorials, you know. And every day you write an editorial and you internalize a little bit and you get better at it.

The other thing is that people think the only way to learn law is to go to law school. And that’s the bar lying to you. You spend a few years writing editorials about law, and you know a lot more law than most people who go through law school. It’s spotty, because I couldn’t pass a first-year torts final right now. But I could teach a lot of classes. It’s a very different kind of legal education. So, you know, it’s a funny thing. I’m not sure I would recommend it to others that they do it that way, but it’s the way I did it.

In one of your interviews with Julie Hilden, you said that you wrote about Ken Starr partly because you were dissatisfied with the existing literature. Was this also a reason that you started Lawfare, and what did you think was lacking in the national security debate?

Jack and Bobby and I were looking to create a forum for a particular kind of writing that we were doing, and not because we were particularly trying to plug a hole in the debate. But we very quickly realized that there was a big hole in the debate. We had been frustrated for some time that the debate was so dominated on the one hand by the human rights groups and civil liberties groups, and on the other hand, the litigating position of the federal government. And there wasn’t a place that was a home for just strong analytic writing that did not assume the government was the problem in every case. And so we discovered that there was a real hunger for that kind of writing, and the site really took off because there was this hole in the debate. We quickly realized that we were filling it. I would say within a couple of months of starting LawFare we were pretty self-consciously trying to fill that discussion — trying to write to that space in the debate. And that has been the animating spirit of the site ever since.

Lawfare was probably kind of small when you first started it. Now it’s grown into a very big, very popular site. Have you consciously changed the style or content of your writing now that your audience is more mainstream?

Yes and no. We started the site to speak to 5000 national security lawyers, academics, journalists; I just made up the number 5000. But I mean, not friends and family, but small. And it was a professional audience that we were trying to provide a service to. That number kept growing, but it stayed a broadly professional audience until relatively recently. Over the last two years, it has broken through to a mass audience, and last year we had a 11.5 million visits on the site. Those people are not all capable of using the vocabulary that the site traditionally uses. And so we have this problem, which is how to serve this new readership that is really hungry for the work that we do, and that I feel a real obligation to. If they’re coming to Lawfare and they’re willing to do the work to read it, I feel an obligation to service that readership.  

But I also don’t ever want us not to keep faith with our core readership and do the work that we started the site to do. The tone of those types of writing can be very different in the level of altitude. If you look at the piece that Steve Vladeck and I just posted, that’s a dense legal analysis. And we made a point of writing it in a way that was not dense. We want people to be able to read and engage with it, because lots of people want to. But we also always want to do the work so that it’s credible to the legal audience — that is, the core audience. That is a very difficult dance, to try to serve the new readership while keeping faiths with the old readership.

Sometimes you do that by writing a piece in an artful fashion, and sometimes you do it by saying, “OK. This piece is for the 200 people who need it, and it’s not for anybody else.” And you just get down and dirty and get dense with it. Sometimes you’ve got to do that, and sometimes you say, “This piece is for the new readership. It’s not for the old readership, but there’s a lot of people out there that need an explainer about, say, what a grand jury subpoena really is.” My core readership doesn’t need help on that. But there are a lot of people out there that need help on that. When everything’s going well, you can marry the two types of writing and do it in one post. When everything is not going well, you sometimes do need to choose.

It makes sense that you speak so eloquently about this, because I saw that you teach a class on writing for non-legal audiences.

Well, you say that in the present tense. I taught it once. It was a fun little experimental course that I did, that I’d never taught before, so it was just something that I did this year. But yeah, I have given this a lot of thought.

How did that class go?
It was a lot of fun.

Was that your first experience teaching in a classroom?
Oh no, I’ve taught a fair bit. I guest teach in law schools all the time, and I teach undergraduates fairly frequently.

How hard is it to balance your Lawfare responsibilities and your teaching gigs with  book-writing?

I don’t sleep a lot. Sleep’s overrated. You know, Richard Posner, the great judge and public intellectual, who’s written more books than most people have read, was once asked, “How do you write so much?” He responded, “I don’t waste a lot of time watching sports on television.” I’m not nearly as prolific as Dick Posner. But I don’t waste a lot of time watching sports on television.

The Nationals have been pretty good over the past few years.

So I’ve heard! 

I’m a Yankees fan, and they’re doing super well. I probably waste a little too much time watching them.

That’s okay, you’re 15. Eventually, you have to decide what’s important. And for a lot of people, that’s what’s important. But we make choices, and one of the choices we make involves how productive we want to be.

Other than working hard and not sleeping, what’s your secret to being productive? Compared to someone else, who might do these things and not have a successful career. 

There are three elements to productivity. One is having something to say. You know, a lot of people don’t have anything to say. That’s not because they’re bad people or anything — it’s just because they don’t have that much to say, and that’s okay. And the problem is limited to the fact that they beat themselves up about it and they feel like they really should. Maybe the answer is that’s just not their role in life. There’s lots of other things to do than to have stuff to say in public.

The second category is people who have a lot to say and aren’t good at the execution of it. They have a lot to say, but they have a lot of performance anxiety, they get writer’s block, or they just aren’t efficient about their use of time. I don’t really know what to say to those people. There’s a certain discipline and training. There’s a certain character type that lends itself well to getting up every morning and writing stuff. Some of it is trainable, and some of it is probably characterological.

And then, there is this other factor. That’s practice. And people think they should be able to just write a book. Writing a book is fricking hard. And like anything else that’s hard, it’s hardest the first time you do it when you don’t know how to develop a rhythm about it. The tenth time you do it, you kind of know how to do it. By the way, writing editorials every day for nine years is a really good way to practice being productive. So I don’t really know the answer to your question. It’s some combination of characterological discipline that lends itself to productivity, a kind of set of disciplinary training over time, and just practice at the tasks in question. All I’ve ever done with my life is read documents and write what I think of them. If that’s all you’ve ever done, you develop a certain fluidity with it.

You said earlier that you had a pretty easy time walking into a government building and just identifying important information.

I’m good at that.

 Yeah. Why are you good at that?

I don’t know. By the way, that’s the same skill as reading the newspaper and having something interesting to say about what you read. It’s the skill of looking at a large pile of information and figuring out what’s important, figuring out what questions to ask. Who’s the person that you read about in the newspaper today who you wanted to pick up the phone and have a conversation with. What are the questions you wanted to ask that person. Those are skills, those are questions — some people are better at those questions than other people.

 Do you think people can be taught to know how to say interesting things?

I don’t know. Yes. I think there are a lot of people who have interesting things to say and are not good at believing that about themselves. And so it sometimes has to be teased out of them. I do think there are people who are just brimming with interesting stuff. A lot of them find their way to me, because Lawfare is kind of an interesting outlet for that sort of thing. Those people are really — there is a characterological element of that. When you meet somebody who has interesting stuff to say about all kinds of things, you really notice it.

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Other interviews conducted by Anna Salvatore: Neal Katyal, Leah Litman, Ian Samuel, Adam Liptak, Art Lien, Gabe Roth,  and Fane Lozman.