The next big thing

Q&A/Penn Law professor by day, novelist by night, Kermit Roosevelt talks about his journey from literary rejection to being named 'The Next Big Thing.'

Kermit Roosevelt wanted to be a philosopher. He ended up at Yale Law School instead.

Once he got there, he felt mostly disappointment.

Law school, he says, was too easy.

“Law school did not seem to be as intellectually demanding as philosophy,” Roosevelt said. “There were interesting legal questions, but they weren’t the sort of things that great minds had thrown themselves at for thousands of years.”

In other words, the easy road does not appeal to Roosevelt, whose career as a lawyer, law clerk for Supreme Court Justice David Souter and, now, Penn Law professor, prove he’s always up for a challenge.

Over the past three years, Roosevelt has directed his energies toward a big one: Literature.

And after spending countless nights and weekends at the computer—sometimes staying up until 5 a.m.—Roosevelt finally saw his debut novel, “In The Shadow of the Law,” published earlier this year. The novel, which tracks the experiences of associates and partners at a major Washington, D.C. law firm working on both a pro-bono death penalty case and a class-action lawsuit against a chemical company, has scored tremendously positive reviews. The New Orleans Times-Picayune dubbed Roosevelt “The Next Big Thing,” and the Washington Post called the novel a “readable, informed, sophisticated, often devastating look at the practice of law.”

The success has been both surprising and gratifying for Roosevelt, who saw three earlier novels—more “literary” works, he says—rejected by publishers.

We sat down with Roosevelt this summer to chat about the book and his experiences writing it. Turns out “In the Shadow of the Law” may owe more to George Lucas than John Grisham.

Q. Where did the idea for this book come from?

A. I had done some writing in the past, and had decided I wanted to try and write something that would appeal more to people than the other stuff I had been writing. Given the different jobs I had had—as a law clerk, as an associate and the difference experiences I had as a law student—I thought one thing that would be interesting to do would be to look at the legal system from the perspective of the people occupying all these different roles.

Q. Did you draw on a lot of your real-world experiences for this book? If so, were you concerned about how your former colleagues would feel about that?

A. Not in the sense that the characters are actually based on actually people or actual cases, but for the atmosphere and feel of the book, certainly I did [use my experiences]. But the lawyer characters don’t really resemble anyone that I worked with, and that’s pretty clear to people who know me or worked with me. I also didn’t think of the characters as being quite as loathsome and miserable as some of the reviewers seemed to find them. I had a certain degree of fondness for all the characters in some respects.

Q. Was this novel radically different than what you had written previously?

A. This was more character-focused and more story-focused and more idea-focused. What I had written before was just language-focused. I was trying to make the sentences interesting. I was not worried as much about plot or characters. [Writing plot] was a little bit of an adjustment, so it was something I had to tinker with.

Q. Did the writing come easily for you?

A. It all went pretty smoothly. Writing the first draft took about a year, and then through the first round of revisions, which also took about a year, I doubled [the book length] and then after that spent another half-year trimming and adjusting parts. I was surprised at how easy the revisions were. Each time I finished a particular version, I figured, “Well, this is finished,” and thought it had perfect artistic unity and that if you tampered with any part of it you would mess the whole thing up. But once I went about trying to implement some of the suggestions my editor had given me, I invariably found it got better.

Q. Where did the editor help you the most?

A. The first thing he told me was to make the book twice as long. That’s when I focused more on the characters. That was also when I started going back more into the past, instead of just focusing on the present. It was significantly smaller before—not quite half the length of the current book, but close to that. I found it surprisingly easy to make it longer, just because once I started getting a feel for the characters, it was easier for me to write more for them. And it was just fun to put the finishing touches on the book.

Q. When did you find the time to spend this much time writing?

A. I did nights and weekends. On days when I didn’t have to teach and in the summer I had a good routine here—I would come into the law school for 4 or 5 hours during the day, then go play some squash, go home and take a nap, then have a pot of coffee and stay up until 5 a.m. or so writing. Then I’d sleep until 1 or 2 p.m.

Q. Did you have a sense early on that you had a winning story here?

A. No. I just started out thinking that since nobody wanted to publish my literary novels, I was going to write a legal thriller. I started out feeling it didn’t have to be a good story, that this was just a very technical exercise that I should be able to do. And then I started to think there was a lot more possibilities and potential than I realized at first in both the genre and the type of story I had.

My mother had given me a book called “The Writer’s Journey,” about how mythic structure underlies the plot of various books and novels. “Star Wars” is the one everyone points to. So I adopted that structure. You can just about map the characters in this book onto the “Star Wars” characters, with a couple of twists where I was trying to subvert the “Star Wars” characters. Nobody’s picked up on that.

Q. Were you very disappointed when your earlier work didn’t get published?

A. Yes, although it was a disappointment that I was getting used to. The first two novels I sent out, I was just sending to publishers myself, which is what people had advised me to do, but it’s almost impossible to succeed doing that. For the third one, I had an agent and thought I had a more realistic shot with that one, but it also came to nothing. With this one I had a different agent, and I was cautiously optimistic that she would be able to get something done.

Things happened pretty quickly. She shopped it around and got a couple of people who said they were interested. I went in to talk with them about their visions for the book, and how they wanted to see it develop, then I picked one and took another two years to do the revisions and it was another six months before it came out.

Q. Have you been surprised by the great reviews? One newspaper called you “The Next Big Thing.”

A. That was the Times-Picayune. Yes, I was pleasantly surprised. I really didn’t know what to expect. I was hoping they would be positive, but didn’t expect to get as much media attention as I did.

Q. Have you learned anything about the publishing business in general through this process?

A. I’ve learned you should take every opportunity to sign your books, because once you’ve signed them, the bookstore can’t send them back.

 Kermit Roosevelt