How It All Started: Q&A With Best-Selling Author Jeff Pearlman

As I continue to gain traction in the sports writing world, one question that continually gets asked of me is, “Aaron, how did you get started in sports writing?” It seems like everyone wants to be a sports writer, reporter or TV personality, yet no one is entirely sure how to go about getting there

For me personally, it was easy. I wanted to write about sports, thought I had some valuable opinions, and when no one would hire me to do it out of the gate, I decided to start this very website that you’re looking at right now. I know, I know, that’s not a very good or inspiring story. Then again, I haven’t really achieved all that much success yet either.

So with that, instead of trying to answer the question myself, I took a different approach, and decided to start a series of long-form interviews with some of the most successful people in sports media. These won’t be podcasts (since some folks can’t listen at work), but instead, written out interviews, which you can read, digest, and then if you find something valuable, be able to go back and reference them at a later time. The ultimate goal is to teach anyone who wants a start in the sports industry that there are a lot of different paths to success, and you don’t need to go to Syracuse or get hired by ESPN right out of school to get there.  What’s much more important is being smart, creative and resourceful; something that I suspect will be a common theme in these interviews.

No one personifies that last point better than the first person I’m interviewing for this series, former Sports Illustrated staff writer and current best-selling author Jeff Pearlman.

Jeff is interesting, in the sense that not only did he decide at an early age that he wanted to be a sportswriter, but that he actually declared it to his parents, telling them in his early teens “I will write for Sports Illustrated.”

Eventually he did, but not without taking several unique turns along the way, including entering his name into the 1993 NBA Draft after his junior year at the University of Delaware (despite having never played college basketball), and working as a fashion and food writer as his first job out of college. From there he got to Sports Illustrated, and is now a best-selling author, with five books out, including the recently released "Sweetness" about Water Payton. Maybe my favorite sports book of all-time, “The Bad Guys Won,” was also written by Pearlman.

So how did it all start for Jeff Pearlman? Let’s take a look:

Q: So Jeff, I hate to start with the cliché question that you get in every interview, but I know that when you were young, you spoke with your parents and told them, “I will write for Sports Illustrated.” What was it that compelled you to go out on a limb as a young person and make a statement like that, and then what were the early steps to start on the path toward achieving that goal?

A: Yeah, I don’t remember what actually led me to say that. It was weird since I haven’t had that many moments in my life where I really felt like I knew it was going to happen. But I really did.

I remember I was 14 or 15 and I told my mom (I will write for Sports Illustrated), and my mom said “Well, you’ve got to be realistic, you should be a lawyer,” like any Jewish mother would. And I said, “No, I’m telling you” (I will write at Sports Illustrated). So when I did get hired at Sports Illustrated it was very emotional for me, because I felt like I’d fulfilled something I’d sort of dreamed of.

The early steps were really pretty basic. I wrote for my high school newspaper and from an early age I was looking for stories that were a little different… I remember there was this story in the New York Times about a homeless basketball player who’d signed to play at the University of Maine, and remember being moved by it. So I called the kid’s high school and got him on the phone, and did a profile on the kid.

So it’s always been sort of about reaching beyond the normal and looking for stuff that’s out there. My dad was a writer- he’s actually an Executive search guy, a head-hunter by trade- but he used to write columns for our weekly newspaper, and it used to really inspire me, and got me eager and enthusiastic to write. I saw how he wasn’t a great athlete, he didn’t look like Tom Cruise, but he was doing something different, something to make him stand out. And I think that inspired me.

Q. Going back to that original proclamation “I will write for Sports Illustrated,” was it a conscious decision ‘I want to write for Sports Illustrated,’ or more an unconscious ‘Sports Illustrated is the apex of what I want to do, and if I get to Sports Illustrated, it means that I’ve achieved success. Does that make sense?

A. I think it was kind of both.

My goal was always to write for Sports Illustrated. When I was in high school the goal was to write for Sports Illustrated, when I was looking for internships the goal was to write for Sports Illustrated and when I had my job at the Nashville Tennessean I was always thinking ‘How will I get to Sports Illustrated?’ It was like a dangling carrot for me. I always thought I’d be in my early 40’s, late 30’s before I got there. It was always this golden beacon on a hill.

But actually a couple things got me there.

I was a writer at the Tennessean- I wasn’t even a sports writer, but a food and fashion writer, followed by a cops writer- and I kept writing them (SI). The Chief of Writers finally said ‘Why don’t you pitch up some ideas for freelance.’ They didn’t want a profile of Peyton Manning or anything, they wanted unique stuff. And what I did in college at Delaware, I applied early for the NBA Draft. I wasn’t a basketball player, I was a runner, just for one year. But there was a whole sequence of events where I got a call from Rod Thorn, I got letters from the league asking me ‘Who are you,’ and I pitched that to SI, and it ended up being my first freelance story for the magazine.

Again, it’s about doing something that isn’t ordinary. About finding something that makes you stand out or unique or makes people say, ‘Wow, that guy thinks differently.’

The other thing is that when I actually applied officially for a job, instead of sending a normal cover letter, I actually designed my cover letter to look like the front of the magazine. They have letters from the editor on the front next to the masthead, so I cut out the masthead and instead of writing a (cover) letter like: “Dear Sir’s I’m interested in writing for Sports Illustrated,” I wrote a fictitious letter from the editor saying something like “When we first decided to hire Jeff Pearlman, he was an eager young guy. His lifelong dream was to write for Sports Illustrated.”

When they hired me a lot of people mentioned that letter, how it stood out, caught their eye.

I think there’s a real value in trying- without being offensive or egregious or overly desperate- to stand out.

Q. And if I’m not mistaken, when you first got to Sports Illustrated, you were a fact-checker first, right?

I was hired as a “reporter,” and what a reporter did was went through the stories word-by-word with a pen, and circled anything that could be questioned and looked it up. It was pretty arduous stuff. But, because of my background, being a few a few years out of school, they were a little more open to me writing. They definitely gave me some opportunities that some of the others might not have had.

The other thing was, I busted my ass. The best thing I did while at SI was, we worked on a four day work week- which was really cool- and I would always go in five or six days a week. When no one was there, I would take out a directory called the CoSIDA Directory, which lists every Sports Information Director for all the colleges in Division I down to NAIA. I wouldn’t call the big schools, but call Division II, Division III, NAIA, small Division I, introduce myself and ask, ‘Do you have any story ideas whatsoever?” But it couldn’t just be about a 1,000 yard rusher. It had to be a running back with one hand, or a gymnast who moved here from Kenya, blah, blah. I started getting tons of story ideas, and I kept pitching these ideas, and they had to wonder where I was coming up with this stuff. But (from it) I started getting tons of stories, in the Scorecard section (of Sports Illustrated) or other small stories to write.

The other thing was, they used to have things called “Catching Up With,” where they caught up with old cover subjects and wrote updates. I must have pitched 8,000 of those things. For a long time I was the all-time SI leader in “Catching Up With.”

Q. Do you remember any of those under-the-radar stories you did when you were going through the CoSIDA book?

I think it was my first story when I was on staff at SI, there was a guy in Portland named Ronnie Duquette who had the world’s largest collection of autographed sneakers. I saw his name in a kid’s book from like five years earlier and he was mentioned, and I always remembered the name Ronnie Duquette. So when I was at SI, I was like ‘There’s this guy in Portland who follows NBA players around and gets their sneakers’ and that ended up being my first story.

Also I used to Google obscure sports, like….rodeo. I Googled rodeo and found these two brothers Jet and Cord McCoy who were like the hot rodeo brothers at the time. They were both 18-years-old and coming up in the ranks and SI sent me to Oklahoma for a week to drive around in a truck with Jet and Cord McCoy.

I got these amazing, rich experiences just from digging around for these unique ideas.

Q. It’s funny, I don’t know if you’ve heard this story or not, but living in Connecticut, there’s a school, Trinity College, which up until this year hadn’t lost a squash match in I think 13 years. From like 1999 until this past winter, they never lost. And I interviewed their coach last year, and people said ‘How had I never heard this story before?’

A. Yeah, it’s a mistake I think a lot of people make in this business—looking (too much) at the obvious.

For example during the Super Bowl, the storylines were Tom Brady, Eli Manning, Mario Manningham, whatever. Then they mentioned that the Patriots cut this guy from Rutgers (Tiquan Underwood) the day before the Super Bowl. And I thought, ‘What a great story.’ To me, that was the story I’d want to write. How did he spend the day of the Super Bowl?

I just think that for young writers who want to move up, they’ve got to find those stories. The world does not need another Tom Brady profile or Eli Manning profile. Those stories are kind of golden.

Q. Let me transition into what you’re doing now in books. As I mentioned, I really enjoyed ‘The Bad Guys Won,’ as well as ‘Boys Will Be Boys,’ which I really enjoyed as well. How do you pick your book subjects? Because writing books full-time, it seems like you have to pick compelling, broad stories that are interesting to a lot of people. How do you go about picking book subjects that are interesting enough to appeal to a broad audience?

A. It’s actually pretty hard. I don’t have free reign to write about what I want by any stretch, and unless you’re Stephen King, you’re working book to book, trying to sell your next idea off the last one. It’s like being a free agent every time. My dream is to write a biography on Shannon Hoon the deceased lead singer of Blind Melon. But I’d probably sell four copies and would have to be independently wealthy to do it.

As far as subjects, I have some criteria. When looking for a subject I go to bookstores, wander around, see what’s been written, what hasn’t been written. First and foremost I’m thinking what I would be interested in. I think, ‘What subjects would I want to spend two years of my life diving into?’ For example, I wrote a biography about Roger Clemens, and even though I was well compensated for the book, I always sort of considered that a mistake. I didn’t enjoy him (Clemens). I didn’t enjoy the subject. It wasn’t fun. I consider that my weakest book, and it wasn’t enjoyable. So I want to find subjects I want to write about, and they also have to be books that at least have a chance of being on the best-seller. Again, a Blind Mellon book isn’t going to be on the best-seller list.

So I’m always thinking, ‘What at least has a shot?’ and I feel like every book I’ve ever written at least had a shot. Three of them made it (to the best-seller list), two of them didn’t. But they were all big subjects with great storylines, fascinating characters. Even with the Payton book, it made the best-seller list, but I thought it would sell better because he’s got such an amazing story and narrative.

Q. You just mentioned the Payton book, and in hearing you interviewed about it, the thing that stood out was the work that went into it. How you went down to Mississippi a second and third time just to make sure and get your facts straight. Tell us what goes into writing a book that in-depth, because sometimes I don’t think people realize what a grueling process it is.

A. It’s interesting, I never rip books anymore. I may rip a movie, but I never rip a book, especially biographies, because it’s just painful. Not being ripped, but doing the actual work.

Payton was the best example, because I really became obsessive about him; literally obsessive. I probably read 10,000 articles about Walter Payton. I probably spent two years going back and forth, Chicago to Mississippi, Chicago to Mississippi. Two years on the phone. I interviewed 678 people, because my thing is you don’t just want to interview Willie Gault or Mike Ditka, you want to talk to the guys who were the seventh round draft picks who never stuck, you want to talk to the ball boy, you want to talk to every single person who might have a memory of Walter Payton.

That’s the thing about icons. Were Walter Payton alive, he probably wouldn’t remember the sixth round from Bucknell, but the sixth round pick is going to remember his moment with Walter Payton. So I try to find anyone who had any connection to the subject at all. Even if they only have one story, one nugget, you almost become a collector of little nuggets, stories and figure out how to add them all into the book.

And that’s really what my day is like now. Going day by day, clip by clip. It’s really a labor of love.

Q. Changing gears, you’ve been very vocal that your No. 1 job is as a parent, not as a writer or author. Do you want to get back into magazines and feature writing, or do you like writing books because of the schedule it provides?

A. I feel like life is short, and there are probably other jobs I’d like to try in my life. But my kids are eight and five and I drop them off every morning, pick them up from school, I take them to different sports, I know their friends… I’ve never been the kind of dad who doesn’t know how to change a diaper. It really is like a dream for me.

Now I would’ve never said that coming up when it was all Sports Illustrated. I don’t know if I would’ve ever envisioned myself saying that at age 39 that a big part of the dream was that I’d be taking my son to tennis. But it really is.

The other thing is- and I’ve heard other book writers say it too- is that once you write books, it’s a little harder to get motivated to write feature stories. You really, really get into the digging of it all, the research. I mean obviously you research an SI story, but it’s a totally different level. It’s hard, and it beats you down, but the obsessiveness of writing books is something that I really feed off of.

Q. If you don’t mind me asking, do you have a favorite book you’ve done? Or is it like picking your favorite kid?

Payton, easily.

Actually, I’ll rank them for you. ‘Sweetness’ is my favorite, second is ‘Boys Will Be Boys,’ third is Barry Bonds, fourth is the Mets book and fifth is Clemens.

Q. I know you said that with Clemens, you just didn’t like the subject. But otherwise, why in that order?

With ‘Sweetness,’ I feel like I put everything I’ve learned from the other books into that one. It was well researched, it was the best narrative, and of everyone I’ve ever written about, he was by far the most interesting and fascinating figure.

The Cowboy book (‘Boys Will Be Boys’) I really enjoyed the experience. It was a great topic, great subject, fascinating characters and I feel like it had the reporting of the Bonds book with the fun of the Mets book.

The Bonds book turned out bitter, because it came out two weeks after ‘Game of Shadows,’ and it sort of got annihilated. Now ‘Game of Shadows’ was a great book, there was no anger. I feel like the reporting in the Bonds book was good, overall I feel good about that book.

The Mets book I very much like, and that was the subject that was closest to me. But in hindsight I wish I had done some more background on the players. I was a rookie and had never written a book before.

And then Clemens, it was just not a fun experience.

Q. And I was going to ask, I’ve heard you say with the Mets book that there were things you wish you could’ve done differently. What does Jeff Pearlman the author of 2012 know that he would tell the author from a decade ago?

A. Really it’s all about character background. There’s not enough in ‘The Bad Guys Won,’ of (things like) where Gary Carter came from, where Keith Hernandez came from, where they developed who they were.

There were two fascinating guys in Daryl Strawberry and Dwight Gooden, and I barely get into their boyhoods in Los Angeles and Tampa. Now, I really think that’s the backbone of a book. If you really want to understand who a guy was in 1986, you’ve got to understand who he was in 1966.

I feel good about ‘The Bad Guys Won.’ It’s taken on a cult following, which is kind of cool. Especially since being a Mets fan is so sucky, if I can give them a good moment or two, I’m more than happy to do it.

Q. I have to say, I really did love that Mets book.

A. Well thank you. My favorite part of that book was definitely there was this video ‘Get Metsmerized,’ and it was fun tracking down the producer, and George Foster trying to make money.

That little stuff just does it for me.

Be sure to follow Jeff on Twitter, and check out all his work at JeffPearlman.com.

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