Is Will Leitch's Career in a Deadspin?
R A Miller
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Long-time readers of this site know Will Leitch from his debut book, 2003's Life As a Loser -- published with pride by Arriviste Press. Readers of said book know (and secretly love) that Leitch is somewhat of a journeyman wordsmith, plying his trade at venerable institutions such as The New York Times and The Sporting News, at less remembered institutions such as Brill's Content, and at just plain quirky diversions like The Black Table.

Readers also know him as a pretty funny bastard.

So what is the 21st century's everyman doing now? Well for starters you can find (and harass him) at one of Gawker Media's latest projects: Deadspin -- a sports blog that claims among its strengths no special access to sporting events or athletes, slanted coverage of the Arizona Cardinals, and special dedication to the "whole side of sports that, because of either corporate obligations or just plain laziness, never makes it into the public consciousness."

A_P: When the Life As a Loser weekly column ended -- not long after the book came out -- you were working at a stable-if-not-glamorous financial rag, still cranking out Black Table, and seemingly settling into life as a grownup. Now you've gone and chucked it again. Are you crazy or retarded?

WL: Well, both, though my decision ended up more "grownup" than I would have suspected. Working for Gawker Media on Deadspin has been the most fun job I've ever had; I can assure you, writing about sports all day is a helluva lot easier than desperately trying to care about financial stuff that I really didn't. I actually felt kind of bad for my boss at my old job. He was a really nice guy and really believed in me, but, honestly, at the end of the day, I really don't care about Morgan Stanley. So I ended up doing the sports site for Gawker. Other than the nauseating notion that I am a "professional blogger" -- this is the first time I've ever blogged in my life -- the move has been the best one I've ever made. And the pay is more than comparable. I'm having a shitload of fun, and I even get to work at home. Beat that.

A_P: Aside from sitting around waiting for royalty checks we never send you, what lingering effect has the Loser series had on you professionally or personally? Do people still ask about it? Many people felt really connected to you through those columns and/or the book.

WL: Totally. I find it amazing how many people I meet that know the Loser stuff. Writing the columns and the book was the best possible professional move I could have made. It allowed me to do something on my terms, the way I wanted, a chance to show off what I could do. That continues to pay off to this day. I'm very proud of the book, and not just because [Tom] Perrotta wrote the foreword, though I still kind of have to pinch myself about that one.

Personally speaking, writing that column was a joy, but I'm glad I don't anymore. It's nice to just live my life by myself. Plus, if I were writing as openly about my life now as I used to, my girlfriend would kill me. Justifably.

A_P: Now that you're with Deadspin, what's happening with Black Table? Are you as actively involved as you have been in the past? All the principle drivers seem to have moved on to bigger things (Eric Gillin is at Maxim; Aileen Gallagher is at Media Bistro; A J Daulerio is, we assume, nursing his hepatitis...)

WL: A.J.'s actually running Oddjack, another Gawker blog, a really unappreciated one, if you ask me. (Personally, I think Daulerio is the best pure writer we have on the site; it's just a matter of time before people realize this.) Gillin is going to be running Maxim in five years, everyone on the planet knows it and I just hope he remembers me when he becomes the first Jewish president. And Aileen is not only freakishly smart, but she's a much better writer than people realize. (I will no longer do a reading after she's read; she makes me look like an amateur, every time.) Now that I've adequately kissed everybody's ass, I don't know what's going to happen with The Black Table. It is the thing in this world that, honestly, I am the most proud of. Nothing else I've ever been a part of has been as exciting and revolutionary and different and great. The four of us, just doing what we think worked, and people reacting to it. Anyone who reads The Black Table, honestly, is my best friend.

But times change, you know? When we started The Black Table, Gillin and Daulerio were living at Camp Bowery, Black Table World Headquarters, and we were writing and editing most of our stories over Tall Boys and bong hits while screaming at professional wrestling. That evolved into something a bit more professional (thankfully), and we all got really good at bouncing stuff off each other. But it has been three years, and all of us have benefited, tangibly, from our work at The Black Table. We've also all gotten older. Camp Bowery has closed, everyone's hugely busy with other stuff and we just don't get to see each other as much as we used to, which makes me incredibly sad. That is not to say that the quality of The Black Table has dropped; I really don't think it has. But, inevitably, it sometimes has to take a back seat to other stuff. We're figuring out how the BT fits in with our new lives. But we certainly don't want it to ever become an afterthought; when I die, I want The Black Table to be in my obituary.

A_P: Speaking of Black Table, how do your experiences with that site help in the development of a site like Deadspin? Black Table started with nothing and grew into a fairly highly trafficked site -- at least if you put any stock in Alexa rankings. How did you grow that site, and are you using that experience to grow Deadspin? (Or is Denton just writing a check and letting you market like crazy?)

WL: Well, I hate marketing and I hate trying to convince people to do anything. I prefer to just produce quality work and wait for people to find it. But that will only work to a certain point, and it will only work very slowly. I think Deadspin is good, I'm very proud of it, but this isn't an art project, you know? It's not supposed to be a cult hit. It's a site with advertisers and page views to hit. I've found the best way to do it is to reach out to the rest of the blog community; there's so much great stuff out there, and I feel like it's extremely important that people see it. So Deadspin's a good place for that. And being a part of Gawker Media has been an immeasurable help, not just because of their larger sites, but because of the experience, smart people there. They all know what they're doing much more than I do, so I try to tap into their knowledge as often as possible. But the bigwigs there seem pleased so far. Personally, I don't check the traffic numbers; if I'm doing something wrong or we're not getting enough people, I'm sure they'll let me know.

A_P: Seriously, getting another crack at working in sports journalism has to be a heady experience for you. We've appreciated your love of sports since we kicked your ass in Yahoo's Pro Football Pick'em last year. What do you want to accomplish with this job?

WL: Honestly? I have no idea. I just want to put out a good product that people enjoy. I want this to continue to be as fun as it has been so far. And I want it to help sell my books and get my name out there to do more stuff. I did an interview with 50 Cent for Maxim, and I was pretty amazed by how incredibly intelligent he was. He said something that stuck with me, something along the lines of, "Listen, I'm a businessman. To me, it's just exciting to have the opportunity to play on this big a playing field. I can run with the big dogs now." That's what I want out of this; to get playing on a bigger playing field. If I do my job right, Deadspin will continue to be a very fun read, I'll continue to bust ass on it and even more opportunities will come up. The only thing in the world I know how to do is write -- OK, I'm also very good at Tetris -- and whatever allows me to keep doing that and only that is exactly what I'm going for.

A_P: You rip on a large number of your sports-scribe colleagues on a pretty regular basis. Do you worry that that may come back and bite you later on, or is this a "respect-not-love" ploy, or is the whole thing tongue in cheek?

WL: Well, everything on the Gawker sites is somewhat tongue-in-cheek, but I really try not to be a negative asshole. I mean, I like sports. I like reading about sports and watching sports and pretty much everything involved with it. Anything I say that's negative is pretty much what anyone who watches sports thinks is negative. I have a ton of readers who are actually sports journalists -- some of the people I poke fun at, actually -- and their reaction is almost always positive. They usually tell me how envious they are that I can write whatever I want; they wish they had that kind of freedom.

A_P: What has been your favorite post on Deadspin so far?

WL: The Kyle Orton drunk photos. The guy who actually took those just sent them to me. (His ex-girlfriend is right next to Orton in those pictures.) That was so cool that someone saw the starting quarterback for the Chicago Bears drunk at a bar and thought, "Jeez, I gotta take a picture of this and send it to Deadspin." That's the best.

A_P: You have a new book coming out, called Catch. What's it about?

WL: It's a novel about a kid from (yes) my hometown who is trying to figure out if he wants to go to college or not. It's more exciting that it sounds. I'm very excited about it; it's the first time I've ever written fiction. I think it turned out well, actually. Writing another one now. I think anyone who liked Loser will be into it. I hope so, anyway.

A_P: What else do Will Leitch fans need to know -- i.e., justify your existence for the previous two years...

WL: You should buy my girlfriend's book, which comes out in April 2006. It's called "Family And Other Accidents," and it's about a thousand times better than mine. And I now live on the Upper West Side of Manhattan, which means I accept all your scorn. Oh, and I still have my hair. I just turned 30, and I'm still not going bald. That's very pleasing.