Will Leitch Leaves for New York Magazine, but He'd Like to Be Deadspin's Tom Brokaw

Will Leitch has spent the last three years as the web's most influential sports blogger, and now he's joining the dreaded mainstream media.

New York Magazine is about to become his home, but before he leaves sports blogs behind, he agreed to talk to me for an interview in which we didn't discuss Buzz Bissinger (other than him assuring me that he had been talking to New York before the Bissinger blowup -- "it's not like they thought, Oh, that guy was on a TV show, let's get him'") but did discuss Deadspin's past and its future.

What will Deadspin look like post-Leitch? He told me, "I guarantee you, Deadspin is going to be considerably larger in a year than it is now." A full Q&A is below.

Why leave Deadspin now, and why for New York Magazine?
I've written for New York for a while -- my first piece for them was actually in 2004. My editor there, Hugo Lindgren, I've known since back in the Black Table days, so I've actually been working with him for a long time, and I enjoy working with him.

I wasn't really looking to leave Deadspin, because it's really fun, but I did tell the New York Magazine people I'd like to keep working with them, and it sort of turned into an accidental negotiation where they put the offer out there. New York is one of my absolute favorite magazines, one of the two or three magazines I read cover to cover. It wins National Magazine Awards. To have them wanting me was a cool thing. Also, I'm going to be doing long, 8,000-word features for them, and I'm looking forward to that.

I'm also making sure I diversify a little bit. We were discussing trying to split the baby, almost having more of a figurehead role at Deadspin while doing this, but I thought if I were going to do it I had to do it right. Deadspin has evolved from the days when it was just me and Rick [Chandler] doing it, and it's in pretty good hands. I'll still be writing for the site, but I also don't want to be hanging over the new editor's head.

Do you feel burned out? Is this part of the trend the New York Times has reported on of bloggers working so hard they drop dead?
I'm on my fourth heart attack, but I'm not burned out. No, I've never felt burned out. Before Deadspin I was working at a trade publication pretending to care about Morgan Stanley, so for me to be able to write in my own voice about stuff I cared about was exciting. People said I would burn out, but that really never happened. It's actually still really fun to me. There are still things I do that aren't fun -- I do payroll, that's not fun -- but I still wake up in the morning and write and assign and edit things that I care about. Having not done that for a very long time, I've always appreciated that. If the New York Magazine thing hadn't come along I would have done Deadspin into the forseeable future.

When you look back at your time at Deadspin, what are you most proud of?
I'm most proud of how many other people started their own sites. There were sites out there before Deadspin -- Free Darko is older than Deadspin, Can't Stop the Bleeding, Mr. Irrelevant, all of those sites have been around, but I think Deadspin helped people think "Hey, it's really this easy." I think that's actually a really good thing. People get excited about the notion that they can just write the way they want to write, not write an AP inverted pyramid story.

I really think a watershed moment in the site was when Kissing Suzy Kolber launched. Whatever you think about the quality of their site -- I think they're great, not everyone agrees -- it was so awesome that Deadspin commenters approached each other and said, "Hey, that screen name is funny, so let's get together and do this." And it grew organically. Obviously, you and I know there are a lot of junk blogs out there, but there are a lot of good ones that launched that were inspired by Deadspin. There's so much more quality stuff than there used to be -- there's no sports fan who's under-served. And when I first started the site I thought there were a lot of fans who were under-served.

Do you regret anything you've written at Deadspin?
Yes, like anyone who's ever done anything for public consumption in the journalistic forum, whenever you get something wrong, you regret it. The best example is the Pujols HGH thing. You know, sometimes you get burned by a source. Any journalist out there in any medium or any form. But that didn't happen that often and when it did happen I felt like I had to fess up to it.

But whether you agree with my justification for the stuff I've written, I had my justifications. So I don't regret anything as far as my standards, but certainly I do regret if I got something wrong.

When FanHouse launched, you wrote that with so many different writers, "the collage of voices could potentially cause us a little whiplash." But now Deadspin has reached a point where there's a collage of voices and it's less dominated by your voice than ever before. Were you happy with that, and does that play a part in the fact that you're leaving?
It definitely is not playing a part in the fact that I'm leaving. Certainly, there is a little part of me that is wistful for the days when it was just me and Rick. That is not to say the site isn't improved -- when you look at what A.J. [Daulerio] is doing, he's doing really good stuff. I'm wistful for it not in a quality way, I'm wistful in the way that middle-aged sports writers are wistful for the days when Mickey Mantle was just a guy who hit home runs. I still think everything on the site is generally in the spirit of what I've tried to do.

I do think I'm a better writer than I am a copy editor -- and those hockey guys, I'm still not sure what they're doing -- but that was just a different time. Deadspin has a lot of writers, but looking at larger sites, we're bare. I'm not sure Deadspin would have been successful if it had launched the way it is now.

The one decision that was kind of forced on me that I didn't like was the decision with the redesign where you had to click on the posts to read them. But that's the way these things are going to work now. It makes absolute sense, and I learned to work with it and actually grew to enjoy it a little bit.

FanHouse, if it would have launched three and a half years ago the way that it is, people would have been so overwhelmed, but now I think people can sift through and handle it better.

Will you blog at New York Magazine?
I'll be writing a weekly column for their web site, but I will not be running a blog. One of the great things about New York is they have embraced the web to the point where when I do stories for New York or writing for the web site I'm filing generally to the same set of editors. There's not this idea that there's the "web people" and there's the "magazine people." It's a magazine that understands the web. John Heilemann is one of the best political writers in the country and he writes for the web site all the time.

I'm guessing New York won't let me write that much about Rick Ankiel.

Will we see your writing anywhere else?
Yeah, I'll still be able to write for other places. The Sporting News is re-launching in September and I'll be writing something for them. New York does not have a rule where you can't write for other publications, and I'm glad because that would have been a sticking point. They will be my full-time employer so they get my Grade-A stuff, but no, there will be tons of places, I'm working on the next book now and they're very encouraging of all that stuff.

New York recognizes that the way to make your magazine good is to make your writers happy. Too many publications go on the assumption "you should be happy that we let you write for us." Yahoo Sports is like that, not letting their writers write anywhere else. I think it's great that MJD and Skeets and Wyshynski are getting a large audience, but I don't think keeping them from writing for other places is a very smart long-term thing for Yahoo to do at all.

Will you keep doing New York Times op-ed pieces?
No, I won't. That's the one restriction New York has: You can't write for the New York Times or the New Yorker, and I think that's fine. It is a shame because I had been talking with the Times about doing a more regular online column and op-eds more often, but both the Times and New York didn't want me doing both -- the Times actually had a much larger issue with it than New York did. I think everybody understood.

What does a contributing editor at New York Magazine do?
Basically, everybody has a different deal. Jay Mcinerney has a contributing editor title for New York, and I think he does like one thing a year. But he's Jay Mcinerney. John Heilemann is also a contributing editor, he's in there every week, they have different deals for different people. I have a certain number of words per year that I write for the magazine. If I go past that number I get paid like a freelancer.

[Leitch declined to give the number of words but said he expected to average about a column a month for the magazine, three or four long features a year, and some online content: "I don't think they're going to be lacking for productivity from me," he said.]

Did Gawker Media try to keep you? Was there a bidding war for your services?
I would definitely not classify anything as a bidding war, but certainly when I went to them and told them about this they wanted to keep me and I think made a pretty good-faith effort to keep me -- to the point where it was touching.

Nick Denton would say so if he thought I was making a mistake by leaving, and he said, "I think this is a really good opportunity," which I thought was very nice. Whatever changes Gawker made, I've literally never had a substantial issue with anything they've ever done -- never personality problems. Nick is really smart, he finds good people to do good things and stays out of their way.

It's always funny, when I was on the book tour the most common question I got was, "What's it like to work for Nick Denton?" As if he had us down in a dungeon somewhere. He's actually a very friendly, very personable, very nice guy. Because he's secretive about his personality a little bit and because he tweaks members of the media he seems like this mysterious person. I can tell the world, Nick is a very nice guy who's been nothing but good for pretty much everyone I know who's worked for him.

You said you'll still be writing for Deadspin. What will you contribute?
I'm glad to be able to help them with the transition. A lot of it will depend on whoever the new editor is. If the new editor doesn't want me around anymore, that's his or her decision, but the way I would imagine it is almost like when Tom Brokaw shows up on MSNBC for election coverage. We know he's retired, but it's a big story and we figure we'll bring him around. Whoever takes over the site, it's their site.

How do you think you have changed the sports world over the last three years?
I don't think any influence Deadspin has had is because I'm brilliant, but if anything it's that there are more options now and more accountability in many ways. The quintessential example is when Michael Irvin made his comments about Tony Romo on Dan Patrick's radio show. Five years ago that would have been gone into the ether and no one would have known anything about it.

But now what happened is that it was seen enough by these citizen checks and balances that ESPN had to respond. That's something that five years ago would have been unfathomable. That's changed dramatically and I think that's great, not just for sports fans, but for ESPN -- there's accountability, there's a little more transparency than there used to be. I think Deadspin has probably had a role in that.

If there's one criticism I hear of Deadspin that frustrates me it's this idea that Deadspin has changed the sports world by doing nothing but posting dirty pictures. I think that's because the Roethlisberger photos or the Leinart photos were the first thing that introduced a lot of people to the site. We've actually run maybe 10 of those pictures, but that's what people remember.

Now you've got a site like TheDirty and they're doing their thing and they're getting their readership, and it's not the same as my thing, but they have legitimate news value. You can't tell me that the Matt Leinart photos are not newsworthy. Ask anyone who covered the Arizona Cardinals if those photos are newsworthy or not, if they contributed to an already developing story that was being written about Leinart.

I get tips every day with a photo of an athlete in a bar having a drink with an attractive woman, and that's not going to make the cut. They have to have news value or, more important, be really, really funny.

One thing a lot of people don't know about you is that, until you got the Deadspin job, you considered yourself more a "movie guy" than a "sports guy." Does a desire to cover the movies play a part in this decision?
I would say there's a desire to not just be shoehorned as a sports person. That's definitely true. I confess that there's some part of me -- my dream job is still being a film critic somewhere, but I kind of think the way things are going, in 25 years there aren't going to be any film critics.

People who don't understand Deadspin think, "They're just sports-obsessed." To me, one of the reasons I think I had a different perspective is that I'm not that sports-obsessed. Obviously, I love sports, but I'm not obsessed with it, frankly, the way that people who work in sports are obsessed with it. To them it's work -- and I never wanted sports to feel like work. That's why any time I get an offer to write something that's not sports I always take it and I'll be glad to do that a little more.

Deadspin editor is the dream job for dozens or maybe hundreds of people who have their own sports blog as a hobby. What do you think Gawker should be looking for in the next editor?
They need to have someone who understands the space. Not that it has to be someone who does it the way I do it -- they could take it in another direction -- but someone who understands where Deadspin's place should fall in all this. To me the goal has always been a site that is for fans. That sounds limply populist, but I mean that more in a way that it's not writing for other people who write about sports. You have to be true to the people who actually consume and actually care about this stuff. Otherwise you become Skip Bayless. Deadspin should always point out phonies.

I don't think Deadspin should be, "Who's the MVP?" That's a fine conversation for sports fans to have, but that's not what Deadspin's role is. But if they hire someone who disagrees with that, let them run with it. If that happens they won't need me to be the Brokaw.

Do you think A.J. Daulerio is the favorite to be the next editor?
I wouldn't know, but I think he'd be awesome. I think A.J. is really really good and would do a great job. He's respected by people who are really into this stuff.

I don't know who the favorite is. Whoever it is, it's their site. I'll never say, disapprovingly, "Look what Deadspin's become." It's going to be hard for whoever takes over. Readers have gotten used to a certain voice and now it will be different. The question Gawker will be asking is, Do we want to make the transition easy or are we ready to go off in a different direction?

What will you miss most?
There's going to be a moment that Monday after I leave -- I've got a week before I start at New York -- I'll wake up and no one's going to be waiting to hear what I have to say. That's going to be weird. It's intoxicating for any writer to write something and within minutes of it going up everyone's responding to what you've done. You can get hooked on that.

UPDATE: Who's Next? Odds on Deadspin's Next Editor