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Interview with Will Leitch
Former Deadspin editor, current New York writer, forever St. Louis Cardinals fan
He’ll be here all week, folks (Photo: Gelfmagazine, via Flickr)
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Before I even turn on my voice recorder, Will Leitch and I have already discussed The Simpsons, Carolina Panthers, New York Mets (my favorite team), Back to the Future Part II, King Kong, Lord of the Rings, and Nirvana. Speaking of the ’90s (and forced segways): Leitch is a bit like a Guided by Voices album (let’s go with Bee Thousand); it’s sporadic and often as soon as you’re focused on something he’s saying, he’s moved onto something else. But he’s also extremely heartfelt and possesses a certain boyish charm, similar to Robert Pollard. Plus, there’s beer. Lots and lots of beer.
The recently married Leitch is best known as the founding editor of Deadspin, Gawker’s sports blog, working alongside current-editor-in-chief, A.J. Daulerio, but he’s also: A writer for New York magazine, running The Sports Section on their website; co-founder of the sadly departed The Black Table, which ran from 2003-2006; and a columnist for the Sporting News. He’s also has written four books, including the recently released Are We Winning? On its surface, it’s a book about baseball, but once you look past the picture of two guys drinking beer at Wrigley Field, you’ll quickly notice that Winning is actually about how baseball shapes the relationship Leitch has with his father. Or about any father and son relationship, really.
Encore recently had the chance to speak to Leitch at, where else, a bar.
I assume you’ve basically heard every question there is about going from The Black Table to Deadspin?
I always get sad when people forget The Black Table. To this day, it’s the most fun I’ve ever had doing anything.
Why is that?
It had a “hey kids, let’s put on a show!” vibe to it. When we started, A.J. was at Philadelphia magazine; Eric [Gillin], who had the best job of all of us, was working at TheStreet.com; Aileen [Gallagher] was working for a private investigative company; and I was working at Registered Rep magazine, covering the financial services industry. I apologize to everyone: I did not uncover the financial crisis that was to come. I was a horrible, horrible financial reporter. As a reporter, you have to have some basic interest in what you’re covering. I did not. Anyways, we would get together twice a week, Tuesdays and Thursdays, and just sit and drink and figure out what stories we’d be doing. We were just paying the bills, and we all come out here [New York City] to try to do something else, and we all got so frustrated because of the dot-com crash. So we said, “Let’s just give it a shot and see what happens.” And it worked.
This was obviously a time before social media, like Twitter and Facebook, so how did you get the word out?
We just started doing it. It started January 2003, two-and-a-half years before Deadspin began, and it lasted three years. The original idea was just to ruin killed stories from magazines. I had just had a story killed, so we were all so frustrated and thought, Let’s just have a place where writers can come and put that stuff. It seemed weird that a place like this didn’t exist on the internet yet. And it just kind of developed its own voice in many ways. We updated all the time and got on Google News, which made a big difference. About two weeks after we launched, Gawker launched too, and they were looking for writers in New York.
To go back and look at the masthead for The Black Table, we were very honored. We had Tom Perrotta, James Frey, pre-Oprah. Roger Ebert, too. By the time I started Deadspin, I think I was ready. I had been blasted by blogs, and I had people who hated my stuff. We’ve talked about having a Black Table reunion week, but we’ve never gotten around to it—yet.
So I guess I can it ask then: How did you go from The Black Table to Deadspin?
My name was out there, and Lockhart Steele, who runs Curbed now but was the managing editor of Gawker then, e-mailed me saying, “Hey, we’re starting a gambling site. We have a sponsor for it and we think you’re funny, so would you be interested in doing it?” I think gambling on sports is wrong—
Don’t tell The Sports Guy.
It’s not morally wrong, but just against what I think sports are supposed to be about. I told them I couldn’t do a gambling site, but suggested that they do a sports site. So I met Lockhart and told him we should try it. He was like, “Nick [Denton] is not going to want to do this because he doesn’t know anything about sports, but I’ll do it.” They told me to give it a shot and gave me six months. It was just practicing writing, and we were told that we’d paid $10 per post. I was so excited to be doing something other than writing for Registered Rep that I was doing 28 posts a day, and they were like, “Okay, okay, slow down.” Because of that, they always considered Deadspin to be found money, and they basically said, “We didn’t think this was going to work, but now that it’s working, let’s just leave them alone and let them do their thing.” Which is good, because my big thing is that I never look at pageviews. Now, working at Gawker and not looking at pageviews is insane, that’s the centerpiece of everything they do. I think A.J. is doing such a better job than I did. If I were still the editor, I don’t think there’d be a Deadspin anymore. For that site to survive, they need someone entrepreneurial, which A.J. has been, and smart. At The Black Table, A.J. was the last person to edit anything, but now, he’s such a good editor. Occasionally, Deadspin will ruin something that makes me go “Uh…” but I’m wrong. That’s why I’m not the editor anymore; that’s why it has to be someone like A.J.
Are you referring to posts like the Greg Oden or Chris Cooley penis pics?
I would have covered those. The larger stories, though—I probably would have covered the Erin Andrews and Katie Lacey stories differently, but that doesn’t mean I’m right. In fact, I’m pretty sure I’m wrong. And certainly the Tiger Woods thing…I would have totally failed that story. For me, the Tigers Woods story is the absolute proof that A.J. is a better editor of Deadspin than I am. And I don’t mean that in a “they just like sex and porn” kind of way. He covered the shit out of that story. A.J. started at Deadspin with the idea of “I just have to keep this alive,” and now Deadspin’s the model of the other Gawker sites, which is thrilling and weird to see. When I write something for Deadspin now, it’s weird. I love it, but it’s obviously not my site anymore. I’m the guy who’s like “Here’s a Woody Allen quote!” but people are wondering, “Where are the drunk hook-up stories?” It’s a dramatically different site now than when it was when I left two years ago, and I think for the better.
When you do have a story on the site, like the MLB Season Previews, do you pitch that or do they contact you?
A.J. was best man at my wedding, so I have a pretty good line to him. And I think he certainly liked those. He was wondering what I’d like the headline to be, though. I wanted them to just say “MLB Season Preview: St. Louis Cardinals,” and he’s like, “No one’s going to click on that.” But that’s what I want it to be! If nobody sees it, I don’t care. I do it because I want to do it and I love it. I obviously would prefer if more people saw it, but it’s not really why I’m doing it. A good example of the opposite of that is the Roger Ebert story. A.J. actually came to me with that idea, and it’s a mix of what he does with Deadspin now and what I used to do. He told me that I should write about this because he was going to be on Oprah and he’ll become like Michael Oher from The Blind Side, ‘cause certainly a bunch of my mom’s friends are big Baltimore Ravens fans now. So, I wrote it and it worked out great. To me, that’s the ideal circumstance of what A.J. does so well at Deadspin and what I like to do. It got a lot of hits and it’s written the way I wanted to write it.
Did you hear about Deadspin being mentioned on Party Down?
I haven’t seen the episode yet, but I did hear about it. I remember when Deadspin first started, I wondered if they did another season of Playmakers, if they’d mention the site. I always remember an episode of some show, possibly Entourage, although I hope not because that’d be admitting I watched Entourage…Anyways, the point is the show mentioned The Smoking Gun, and I know The Smoking Gun guys, and how exciting it must have felt to see something they’ve put their heart in to on this program. But I hope it wasn’t Entourage.
It’s like how Bored to Death portrayed New York last season.
If Adam Moss were straight and an asshole and a guy who loves to go to parties, that’s what he’d be like. I love Adam; he’s so devoted to what he does.
When you think you have a frontpage-worthy article for New York, like the Lebron story, is that something that the editors bring up to?
One of the reasons why I wanted to go to New York in the first place is because I know how good of a magazine it is. Every time I have story in there, whether it’s a small piece or a column, I’m always like, “Holy crap, I’m in New York!” Another reason is because although I was brought in to mainly write about sports, I’m also able to write about other things. Sports are fun to write about, but I don’t want to write so much that I end up not liking them.
My pitches are usually about entertainment, and I will say that I probably get more satisfaction out of a feature about Sarah Silverman or writing about Parks and Recreation than out of a baseball piece. Certainly as a writer, you’re just happy to have the ear of such smart editors. A lot of times, people will ask, “Is it weird working for magazines as opposed to the web?” but I just kind of do my own thing. I had written for New York before, in the exact same voice as on Deadspin and The Black Table. Because of that, I knew I wasn’t going to go there and they’d say, “Now you cover city council.” They knew what I did, and to me, that was one of the most exciting things about working for them. They’re a writer/editor-orientated magazine, and that’s pretty rare these days.
Do you find it tough to write about the Mets and the Yankees when you’re such a die-hard Cardinals fan?
The Mets are such an amazing team to write about because there’s so much going on. Some good, many more not so good. I mean, they’re in the Wild Card hunt right now, but no one thinks they’re actually going to win, which is a fascinating thing. With the Yankees, when they were out of first place, people said, “Obviously they’re going to be back in the first,” and for the Mets to share that kind of air space with a team like that is fascinating.
I remember the day of—I apologize to bring this up—but the day of Game 7 of the Cardinals vs. Mets NLCS series, Jason Fry [of Faith and Fear in Flushing] and I, illustrated with a picture from Heat when Robert De Niro and Al Pacino are talking to each other, we had this big time out before the battle. I remember us talking about how this was the Cardinals last chance, whereas the Mets would have more opportunities after this, and we proved to be very wrong on both of those. I said to Jason, “Give me a case of rooting for the Mets,” and he brought up the Yankees. That wasn’t the only reason, but he said, “We’re the other team in town,” and for someone who did not grow up here, the Mets and the Yankees were just the two teams from New York. Frankly, from my perspective as Cardinals fan, the Mets were a much bigger franchise in the ‘80s…
The Yankees were awful then.
Yeah, the Yankees sucked and the Mets owned the town. People go, “That’ll never happen again!” but look: I’m sure people in the ‘70s were saying there’s no way the Mets would ever be more successful than the Yankees. The Mets are a real fanbase, not a New York fanbase. The Yankees are a New York fanbase. Put it this way: If the Mets and Yankees shared a stadium, it would be called Yankee Stadium.
The Mets are such a fascinating team to write about, but I’ll be upfront with my enjoyment of the Cardinals. As if I, of all people, could pretend I was not a Cardinals fan. Ordinarily, it doesn’t come up. If it hadn’t been for 2006, no one would care.
Enough of that memory. To Are We Winning. When you went to the Cardinals vs. Cubs game that you wrote about, did you have the book in mind or did it come during the game?
I didn’t initially intend for the book to be about fatherhood. I often start something and don’t realize what I’m writing about until I’m finished. Roger Ebert once said, “The muse visits while you are writing, not before.” I knew I wanted to structure a book around a baseball game with each half-inning being a different chapter, but I didn’t know what the larger thing was going to be yet. So I spent most of 2008 going to baseball games, crappy ones, by the way. I kept waiting for a good one, but not finding it. I went to Tropicana Field that year.
Was it as bad as everyone say?
I went with a Mets fan, Jason actually, and he was like, “Oh my gosh, there are places by the park where you can have a drink!”
No chop shops?
He loved it. This was when Shea was still around. It’s not a great stadium, but I thought it interesting that the hallways when you walk into the stadium have all the other games that aren’t the Devil Rays, which I’ll always call them. If you wanted to, you could sit there the whole time and watch the Cardinals game. I don’t know what this says about their fanbase. Anyways, I spent most of that year looking for the right game, and it got to be September. So I thought, Cardinals and Cubs playing at Wrigley. I called my friend Mike to see if he wanted to go, and that was when Dad made his famous, “Why would I go to Wrigley Field? There’s just a bunch of Cubs fans there” comment. The father aspect wasn’t something I thought about being an aspect of the book until I got to the game. You don’t realize your father’s a character until you sit down and write about it. To me, he’s just Dad, but to everyone else, he’s probably kind of crazy.
Has he read the book? Does he recognize that there’s a sort of celebrity around him?
If he has read the book, he hasn’t told me. He didn’t read any of the first three books, not because he didn’t like them, it’s just because he’s not much of a reader. Frankly, it liberated me while writing this book because I knew he wasn’t going to read it. If he’s read it, he won’t tell me, which is exactly what I want my dad to do.
He’s on Twitter now, but all he really knows how to do is respond. If you don’t actually follow Cardinals beat reporters, you’ll have no idea what he’s talking about. At the wedding, there were a lot of people who kept going up to Dad and saying, “You’re exactly what I’d thought you’d be like!” He wondered, “Has Will talked about me to you?” I’m not sure if he’s gotten a lot of renowned out of this, but if he has, I bet he secretly likes it.
When you were writing the book, were you worried about it only appealing to Cardinals fans?
I still worry about it.
Was that the intention?
No. I hope that a discerning reader would put down their team loyalty. One of the most exciting things is people who like the book but aren’t even baseball fans. They get what I’m saying about baseball, but apply it to a larger thing.
Since the book’s been released, have you found yourself being more embraced by the Cardinals fan or getting more mainstream recognition?
It’s early. I mean, right now, yeah, but there’s always going to be the Deadspin thing. There are always going to be people who are weird about the Deadspin thing. I did the pre-game show on the Cardinals broadcast, which I didn’t actually see the video until later. But the actual disdain that the anchor has when he throws it to Will Leitch from Deadspin. It’s like, “Will Leitch…from Deadspin” [ED. NOTE Imagine a snake hissing at the “s”]. I think that’s always going to be there. I’ve found people almost surprised that the book’s as earnest as it is, which to me is a little disappointing. I hope that if people read Deadspin close enough when I was doing it that they’d recognize that I’m not a “Fuck everything! I’m destroying everybody!” kind of guy. The only thing that you control is what you write, and some people will see it and some people won’t.