Toobin looks for the middle ground between the unknown and something that resonates with the reader.

Question: How do you approach long-form nonfiction?

Jeffrey Toobin: Well, I guess, I start with what’s written on the subject. I just sort of do research. Have there been newspaper articles, have there been other magazine articles. Now, one of the tricks with New Yorker stories is you want to pick a story that is familiar enough that people will want to read about it, but not so familiar that they feel like they already know everything and they don’t want to read a whole, long New Yorker stories. So usually when I pick a subject, there’s some stuff written about it but not a ton.

And then, when I feel like I sort of know what the issues are, I kind of work around the edges of the story first. I’ll often talk to, say, with me it’s often the law professor who’s familiar with the story, who can sort of outline what’s at stake, you know, what’s interesting, what’s the hot controversy about it. And then, maybe I’ll start to talk to a more peripheral players in the story. And only at the end or at least the end of the beginning, will I try to interview the protagonist.

Because, I think, in order to ask good questions, you have to know a lot about the subject to start with. So I am a great believer in not going to the main characters first ‘cause I need to educate myself about it so I can ask the right questions. And then, it’s often just a matter of finding scenes. I often think of New Yorker stories in terms of set pieces, in terms of, you know, watching something happen as a reader and thus as a writer. So how can I go and see if I’m writing a profile, see the person, you know, interact, give orders, give a speech, perform, be backstage, just sort of, how can I dramatize the story. One thing that I always worry about, I mean, is that… I am in the business usually of writing stories that have issues at their core.

Is Alberto Gonzalez doing his job as attorney general. You know, what are going to do about Guantanamo. The challenge is to take those issues and turn them into stories people want to read. I always want a story to be a narrative. Here’s how it started and their complications ensued and here’s how it ended. That, you know, it takes you along with you. That it can’t just be about an abstraction and that’s a tug I often feel. So in my reporting, I’m always thinking about how do I make this into a story and how do I, in the famous journalistic instruction, how do I show, don’t tell. How do I show things happening rather than just sort of explain it.

Recorded on: September 5, 2008