October 7, 2008

Some eight years ago, I penned a handwritten letter to Gary Smith asking him how he does what he does.

I’m sure I rambled and sounded lame. I just wanted to know how he wrote these detailed, beautifully written stories that teach you something about yourself and make you understand we’re all burdened with the same inescapable truths. How was he able to explain people in a way that made them look completely different than before?

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I didn’t expect a response. But he sent me a 10-page typed letter offering an explanation that only Gary Smith could. He told me, among other things, to live in a foreign country, embrace complexity and read. And something about not being held hostage by my keyboard.

Best letter I’ve ever received.

I consider Smith the best sportswriter in America. He has written for Sports Illustrated since 1982 and has won the prestigious National Magazine Award an unprecedented four times. The movie “Radio” is based on one of Smith’s stories. He recently released “Going Deep: 20 Classic Sports Stories,” which is a collection of his finest work.

Unfortunately, thanks to three moves, I lost that letter. Smith, however, has not lost his touch. Here’s an edited version of a telephone interview in which we discussed how he finds, focuses and writes those incredible stories.

How did you decide to become a sports writer?

Smith: I just really liked sports as a kid. … Around seventh or eighth grade was when I realized I really liked writing and I was getting good feedback in writing. It just seemed natural to marry the two together. And then as I got into the business more and realized the room for creativity you had in sports writing was often more in the other sections of the newspaper, it reinforced that decision. I guess I felt like I could press the envelope a little bit more and go on a limb a little more, writing-wise.

Did you have any sense you were headed toward long-form, magazine writing?

Smith: I don’t think I knew it, but by my second year of covering the Eagles [for the Philadelphia Daily News], I would start to sit down with players and get their backstories, more than what you could put in the normal coverage on the beat. I started getting more of their life stories and I would ask the editor if I could do something longer.

… Then the magazine editor at Inside Sports, which was a literary monthly magazine that at the time was funded by Newsweek, noticed my writing. He was the first one who offered me a magazine writing job. That, by the way, was John Walsh [senior vice president and executive editor of the ESPN Internet Group].

How do you decide on subject matter?

Smith: It’s got to be mutually agreeable between me and editors at SI. If they have an idea I don’t like, they’re fine if I turn it down. If I have an idea they don’t like, they can turn it down. That’s pretty much how it’s worked — 50-50, my ideas versus ideas that have come from someone in the office.

What makes a story compelling to you?

Smith: I have to smell that there’s ripples to it, that the thing has some dramatic arc to it. To go 8,000 or 9,000 words, it’s got to have a couple twists and turns and somersaults to it. If it speaks to something larger, better still.

Have there been instances in which you’ve gotten into the reporting of the story and you realize the person wasn’t as interesting or the arcs weren’t there?

Smith: A little bit, that’s happened. What it usually does is compel me to start reporting harder around the person. If the person isn’t as revealing as you might ideally like, then you can start pushing even harder to get what you might need from other people around the person.

What other techniques do you use to get a source to open up?

Smith: A lot of times it’s rephrasing a question three, four or five ways. A lot of us have the pat answer or the safe answer or the quick answer, [which is] is the first answer we’ll give. Sometimes it takes that many times of coming back at it in a slightly different way to unlock a little something more. Sometimes it’s just getting the person to trust you more, relax with you more. … Hopefully the central character of the story gains more of a comfort level, and with time, more will emerge.

How much time do you generally spend with your subject?

Smith: Average, it could be about a week and a half or something like that. Not every moment of the day, but whatever they can fit in during that time.

Who was the person that was the toughest for you to get to open up?

Smith: Mia Hamm was a challenge because she was caught in a paradox of wanting to step forward for the sake of soccer and women’s sports, but personally not wanting to step forward. It was a very gut-wrenching process for her. We just kept talking and talking about the process and what I was doing. I was trying to bring her into it so she didn’t feel shut out or threatened by it.

When you approach a subject, what do you tell them about the process? How do you explain what you want to do?

Smith: I just explain that I want to try to understand their lives, what it’s like to be them and operate in their world, that it’s going to be very detail-driven, and it’s probably going to take more time than anything they’ve ever done with the media before. I try to make sure they’re aware of that before we enter into that relationship of writer-subject.

How are you able to reconstruct scenes so finitely?

Smith: By asking a zillion questions. When I sense a scene could really be a compelling one, a revealing one, an important one, I’ll just think of a million little questions about what that moment was like. I talk to other people who might have had some glimpse into it as well. It’s basically painstaking questioning, really.

What piece are you most proud of?

Smith: There’s really not one. The feelings you have about a story end up centering on the people in the story who somehow become a part of your life. That keeps it alive in a way for you and ends up coloring your recollection of the story.

The story I did that became a movie, “Radio,” [“Someone To Lean On,” published in 1996] that’s right up there near the top. That’s because Radio and the coach that took him up under his wing, Harold Jones, have remained a part of our lives. There’s another called “Damned Yankee” [published in 1997] about this guy, John Malangone, who threw a homemade javelin into the head of this kid who was his best friend who happened to be his uncle. That happened when John was five years old, and it created these incredible ripples that prevented him from possibly being Yogi Berra’s successor as the next Yankees catcher. John has remained a part of our lives. So that story is very high up there for me because I think it’s one of the best-written stories. Just incredible material that John gave me about his life and what was going on inside of him.

How does a story’s theme become apparent? What are you looking for?

Smith: I try not to look for anything too much because I might miss something that’s emerging right in front of me. One critical thing to me is staying as wide open as possible and seeing what emerges and then thinking about it a lot. Thinking about what that has to say about human beings in general. There are themes that touch on universal things. That really helps to determine whether the piece is going to work or not.

When you do get into that soil that’s more universal, readers then have a stake in the character because they have felt or experienced some of those things as well. Then the person isn’t exotic or up in a cage somewhere. He or she is one of us and going through things we all go through, whether they’re issues with our parents, how we’re raised, things we’re scared of, things we hunger for, things we move away for, what makes us comfortable.

Journalists are taught to look for the conclusion. What I notice about your pieces is you don’t feel the need to make everybody comfortable by wrapping things up.

Smith: If you’re going in looking for the conclusion, then you’ve just short-circuited the whole journey. [You have to] trust what you find and trust the process to bring you somewhere, but not want to wrap it up prematurely at all. …

The other thing I’ve found is that ambiguity is where the reality lies. It’s much more honest. When you inspect yourself about what’s pushing you to make one decision or another, it’s usually this whole flux of things that are going on inside of you, a whole mixture of things weighing and leaning on the choices you make. It’s not that clean. So writing in a way that just irons out the wrinkles and gets you more to the black and white mode of human nature is really kind of dishonest.

Welcome ambiguity and the complexity because it’s a lot closer to the truth. … There’s a gold mine there if you don’t try to skirt it.

What story did you agonize over the most?

Smith: The one about the Amish Mennonite town in Ohio [“Higher Education,” published in 2001]. At first I wrote that from [the point of view of] an abstract, created village person in the town telling the story … It didn’t render it with as much power as it should have had. That was an example of a story I had to start over from scratch and then pick three main characters to tell the story through.

One of the things you wrote me is that even if you’re not at the keyboard, if you’re thinking about the story, it’s still valuable.

Smith: Yeah. In the rush to get to the keyboard you can be increasing the amount of time you’re on a story. If you head down the wrong road and you’re halfway into the story and you didn’t think it out, you create a longer process.

Jemele Hill is a columnist for ESPN.com.

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