A Q&A with Jeff Pearlman on writing books, his fascination with sex workers and the key to a good Q&A

Every week we will run a Q&A with a wonderful reporter to talk about what’s right and wrong with journalism, their interests and random other stuff. Some are friends. Some are just people whose work we really respect. Some cover sports. Some don’t. Hopefully all will be interesting.

This week, it’s with Jeff Pearlman, a best-selling author of multiple books on topics such as Walter Payton, Roger Clemens, and, most recently, Brett Favre. Not only is Jeff a fantastic reporter and writer, he is also the proprietor of a renowned Q&A series called The Quaz, which features interviews with fascinating people from all walks off life. Here, we talk to Jeff about his career, his website and the secrets to asking the right questions.

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The questions are in bold. The answers are not.

1.We start all our Q&As in the same way–at the beginning. So: How did you break into journalism and what led you to where you are now?

Well, I could cut and paste a long blog post I wrote on this very subject, but that’d be pretty lazy. So… I knew I wanted to be a journalist dating back to high school. I went to Mahopac High, and I was sports editor of the student paper, Chieftain. I was a solid student, a solid athlete, moderately liked but generally just… a kid. Then I started writing, and people started noticing. I wrote a piece on why cheerleading wasn’t a sport, and the cheerleaders (aka: hot popular girls who otherwise ignored me) were incensed. Yelling at me, surrounding me in their short shirts. For the 17-year-old me, that was powerful stuff. Then the baseball coach would get mad at something I wrote, the AD would get mad. It was electric, and I was being noticed.

Took that to college; was a bunch of positions at the Delaware student paper, The Review. Typical college journalist—ripping frat boys, slamming the administration. Again, it was this unbelievable sense of empowerment. But… here’s the funny thing. It was all juvenile bullshit. What began as a love of attention turned, 20-some years later, into a love of reporting, interviewing, understanding, uncovering. I think some of that has to do with my first stop, as a features writer for The Tennessean; and a lot of that has to do with my time at Sports Illustrated. I’d never been around a more intelligent collection of people; a more curious collection of people. It was contagious. You aspired to be great, because so many around you were great. And it was impossible to reach the level of others. But you wanted to; you fought for it; thought about it all the time. Etc… etc.

Anyhow, I spent about six years at SI, wrote my first book while I was there. And, well, here I am.

2. We wouldn’t be doing our job as interviewers if we didn’t bring up perhaps your most famous (infamous?) story: this now-legendary profile of John Rocker. Rocker’s comments in this piece are so well-known that it’s easy to forget that they originated in one piece, written by one journalist. But as a fellow reporter, I’ve always wondered what it was like putting that story into the world. On the one hand, John Rocker is clearly a racist, a xenophobe, a homophobe and more. On the other hand, this was clearly a story that would upend this man’s life forever. How difficult was it to pull the trigger on the piece, and how much, if any, guilt have you felt in the years since?

It wasn’t hard at the time, and — despite what some said — it shouldn’t have been. As a journalist, you work and work and work to get people to open up. It’s the greatest challenge of interviewing: How do I get this person to confide in me? How do I get past spin? Past the PR people and the fear of a battered image? And here’s this guy, either dumb or confident or both, opening himself up. Yes, he was a racist xenophobic asshole; a truly bad man. But at least he had the courage to be honest and put himself out there. It wasn’t my job to protect him. It was to profile him. Why hand back great material? It’s not every day someone refers to a black teammate as a “fat monkey” and tells you Disney World’s employees are “a bunch of faggots.”

Now, the aftermath was different. I felt awful. Guilt? Some. But mainly anger. Major League Baseball has employed thousands upon thousands of ballplayers. They are expected and encouraged to speak with the media. They’re not all going to be open-minded, liberal, etc. These are guys from all over the U.S. This is who Rocker was. I thought all the punishment was bullshit.

3. Lots of newspaper and magazine writers say they hope one day to write books. You’ve actually done it and continue to do so to this day. How difficult was that transition for you? Why did you want to prioritize that over magazine and newspaper pieces and go into this world?

Well, I love being a father significantly more than being a writer—and being a writer kicks ass. And I didn’t want to be away from my family for long stretches. Even though I was happy at SI, I could see a future where I wouldn’t be happy. So I left. My first book, “The Bad Guys Won!” came out, and it was received well. And I could write from home, or nearby cafes. And there was no editor hanging over me. And I dictated the pace, the flow, the narrative. It was pretty amazing. So I wrote another. And another. And another. Seven all told, working on No. 8. And, best of all, I’ve rarely missed a dance recital, a water polo match, a baseball game, a concert, a parent-teacher conference. Kids grow up SO quickly; I just didn’t want to devote my summers to the Brewers and Reds when I could devote them to Casey and Emmett. Books allow that.

4. When authoring a book, it strikes me that the possibilities are endless. How do you go about choosing a topic for a book, like Brett Favre, your most recent subject? How do you know it’s the right choice? What makes a story so special or compelling that you’re willing to commit years of your life to pursue it?

Well, Favre was a quirky one. My dream sports book project has long been the USFL, only I couldn’t get a deal. So I started thinking, “Who could I package this with? Who would make a marketable subject?” And I came up with Favre — huge name, no definitive biography, been retired long enough, iconic. So I pitched the two as a package, and got the deal. And the funny thing — Favre really didn’t interest me. It was so I could do the USFL. Then I started digging, reporting … and it was a friggin’ blast. My favorite project.

To get back to the base of your question, I generally ask myself three things: a. Can the book potentially sell? b. Would I lose my mind devoting two years to the project? c. Has it been done/been done well?

5. Without a doubt, part of being a journalist is having a thick skin and being willing to take criticism. You’ve faced plenty in your career, particularly with the response to your book “Sweetness: The Enigmatic Life of Walter Payton.” Undoubtedly, it was not the first time you got blow-back after a book. What is it like when you’ve poured in countless hours and untold effort and emotional intensity into a book and then have it and you be criticized? Does it make you question your work? What is your reaction process to the reaction?

It’s crushing. Not criticism—criticism is OK. And a bad review or two? Fine. But Sweetness got personal. First, Mike Ditka said he’d spit on me without having read the book. Eddie Payton, Walter’s brother, called me a liar—also never read the book. And Mike Wilbon, a guy I respect(ed), suggested in a column that I wrote it for the money—also never read the book. What hurt was I love Walter Payton, put everything I had into that and really believe in the finished product. And I was being torn apart by people who only read a short SI excerpt. I’ve gotten some apologies, believe it or not. Like from the radio guy who led a book burning. But not many.

6. In addition to your reporting and writing work, you have a popular personal website and well-followed Twitter account. One thing that stands out about your online presence is just how open you are. Your Wikipedia page describes it as “an unusually personal online blog….He has also used the site to write about such intimate issues as seeing a rival book get publicity in Sports Illustrated, where he worked, or finding blood in his feces after using the toilet.” Why have you decided to be so open?

Well, the blog started as a vent. That was all. A way to go, “Fuck! Fuck! Fuck!” And, even as I’ve gained readers, I see it as such a tool. I shit blood, I think, “I’ll write about that.” I get a parking ticket —”Let’s write.” It makes me feel better, and I enjoy the back and forth that comes with it. I also think, professionally, it helps. The guy writing the book is just a schlub in a coffee shop with blood in his shit. He’ll chat and answer your questions and shoot the breeze. Too many media people these days think themselves to be celebrities, and it irks me to no end. We’re so incredibly fortunate to have these jobs; these platforms. I’m a guy who got lucky; a guy with blood in his shit. Let’s talk.

7. Today, you’re the “answer” component of this Q&A, but typically you’re doing the questioning. You have a fantastic Q&A series called The Quaz, which has featured tons of fascinating people. Clearly, we need advice: What is the key to coming up with good questions? What do you think makes for a great Q&A?

Hmm … I find the less famous, the less jaded. And the less jaded, the better interview. I also think—and I really can’t understate this—that far too often people forget to ask the best question around. Namely, “So, what was that like?” It’s a really tremendous thing. I’ll never play right field for the Dodgers; I’ll never be an American Nazi Party leader, or Miss Black Iowa, or a hooker, or the guitarist for Lit. So I want to know, more or less, what is your life like? How does it feel, standing on a stage before 10,000 fans? Making an error in front of 50,000 fans? Looking at a Jew and thinking, “I hate you.” So that’s the money question. And do enough research so you know whereof you speak.

8. You have interviewed a number of sex workers for The Quaz. Why the interest in their work and their world?

Man, they’re the absolute best. First, the stories are bonkers. Second, we’re all fascinated by sex, just as we’re all fascinated by death. Third, they’re so ridiculously accessible. I tend to put out Quaz feelers on Twitter, and while singers, dancers, professors, etc can be hit or miss … sex workers are always game. And some have become truly good friends. Which is a beauty of the Quaz series. My contact list is pretty fat.

9. When you teach journalism to college kids, as you do in your various gigs as a professor, how do you describe the job now? What do you stress and what do you tell them to ignore? What would you change about the way sports are covered and that you don’t want your students to take into their careers?

I tell them there’s always a place for great storytellers, and while the game has changed, the necessary skills have not. In other words: No, there aren’t as many 10,000-word features in 2017 as there were in 1997. BUT … the reporting, digging that went into 10,000 words still applies to 5,000. I also tell them that, thanks to social media, we live in a lazy-ass age of opinions on demand. Skip Bayless, bless his heart, isn’t talented. Wait, he is talented—at writing. He truly is. But the shit he does on TV? Yawn. A dime a dozen. But to report, to tell a story via words—that’s something that transcends time.

10. So to wrap, we’re stealing a beloved feature from the Quaz. Rank in order (from favorite to least favorite): “La La Land,” the New England Patriots, Westchester County, N.Y., Marco Rubio, Newsday, the University of Delaware, Dunkin’ Donuts, Herschel Walker, Skip Bayless, and cronuts.

Cronuts, Delaware, Westchester, Herschel, Dunkin’ Donuts, Newsday, Rubio (I still think there’s hope for the guy), Patriots, La La Land (didn’t see, but not a huge musical guy), herpes, skin rash, Donald Trump, Donald Trump’s hair, Skip Bayless.



One thought on “A Q&A with Jeff Pearlman on writing books, his fascination with sex workers and the key to a good Q&A

  1. Pingback: A Q&A with Jay Jaffe of Sports Illustrated on writing a book, the Hall-of-Fame voting process and the biggest Cooperstown snubs – The -30-

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