New Yorker staff writer, CNN senior analyst and fantasy football fanatic Jeffrey Toobin is a Harvard Law School graduate who has written several books about various high profile court cases. His work includes The Run of His Life: The People v. O.J. Simpson and his most recent book, The Nine: Inside the Secret World of the Supreme Court. At an upcoming talk at the Society for the Advancement of Judaism, Toobin is slated to discuss the impact of Obama’s presidency on the Supreme Court.
West Side Spirit recently sat down in Toobin’s Times Square office, decked with items including children’s artwork and a press pass from the 2006 World Cup, to talk about his writing, where he grew up and who he’d cast to play himself on screen.
WSS: How do you come up with ideas for your pieces?
JT: I would say for 90 percent of my work for the New Yorker, I come up with the ideas. And I frankly consider coming up with ideas to be the hardest part of my job. Because particularly with the kind of work that I do, you want stories that are timely and newsy and relevant, but not duplicative of things that have appeared in other major publications. And so sometimes I will do a story that is very much off the radar and it’s obvious no one else is going to do it. But often I’m doing stories that are in the heart of the news, and I’m concerned about beating the competition.
WSS: Do you understand all the cartoons in the New Yorker?
JT: I would say 90 percent. Occasionally I’m baffled. We have a cartoon issue every year, and at least a couple of times we have done features in the cartoon issues about cartoons that no one gets. But I think that’s part of the appeal, you know? Part of the appeal of the New Yorker is that it’s for smart people, and I consider our audience the million and a half smartest people in the country. If there’s something that’s over their head and over my head sometimes, that’s fine.
WSS: I understand that you are into fantasy football.
JT: I’m newly into fantasy football. This was the first year I’d done it. I’d never done it before, and I’d always been contemptuous of it because I’m a Jets fan, and I always thought that fantasy football weakens your allegiance to your team, and all you care about is how your players do. That’s completely true, and I don’t care, because I was just so into it. Now that my fantasy football league is over, and I won, and now that the Jets are unexpectedly doing so well in the playoffs, I can go back to being a Jets fan.
WSS: You grew up in New York City.
JT: I grew up on the Upper West Side. My wife thinks it’s very ambitious of me to live 17 blocks from where I grew up. I just like the neighborhood where I grew up. But she has become even more of an obsessed New Yorker and West Sider than I am, so it’s not like I had to twist her arm. She just loves the city, and now she works for the city. She works for Bloomberg. She’s the chief talent officer for the New York City school system.
WSS: Do your kids go to local schools?
JT: My daughter is now in college, but they both went to Fieldston. My son is a junior.
WSS: Are either of them interested in your line of work?
JT: Hard to tell. My daughter is a freshman at Macalester in St. Paul, Minnesota. My son is a big soccer player, and he plays for Manhattan Soccer Club, for a team called the Manhattan Phoenix, which is one of the great experiences of his childhood and my parenthood.
WSS: Meryl Streep played New Yorker writer Susan Orlean in Adaptation, so if someone were to cast a movie based on your life, who would play Jeffery Toobin?
JT: You can’t go wrong with George Clooney. That would certainly please my wife and daughter, who are big fans, even if it’s not the most, I suppose you call it typecasting, but if I get my choice, he’s my guy.
WSS: Any advice for budding journalists, like, ‘find a new profession’?
JT: I think the single easiest thing to do in the world is not write. It’s very easy to find excuses not to write. And my advice to a budding journalist is to write, whether for a small paper, a school paper, an Internet publication. Get lots of practice. Try to get paid—even if you can’t get paid.
Jeffrey Toobin appears at The Society for the Advancement of Judaism, 15 W. 86th St., Saturday, Jan. 23 at 1:15 p.m.
For more information about the event, which is free, call 212-724-7000.
Transcript has been edited for brevity and clarity.
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