Exclusive Interview with Will Leitch

Danielle Solzman: Will, thanks for taking the time out for an interview with The Kentucky Democrat. How are you doing today?
Will Leitch: I am well, thank you.

DS: Now for the reason you are here, what can you tell readers about the new book, Are We Winning? Why they should buy it?
WL: Well, I hope it's funny and occasionally moving and isn't like any other book about this subject that people usually read.

DS: How does Brooklyn differ from Mattoon, Illinois?
WL: There are more people in a three block radius in Brooklyn than there are in all of Mattoon. So it's quite a bit different.

DS: One of your earliest claims to fame was appearing on Win Ben Stein's Money. Did you win his money?
WL: I did not. It was not a pleasant experience. He and Jimmy Kimmel, his co-host at the time, were nice, though.

DS: How did Deadspin come about?
WL: I pitched Gawker Media on the idea, and for some reason, they went along with it. I hope their instinct was proven correct.

DS: You stepped down back in 2008, right? Why was that?
WL: I was ready for a different challenge, and it was clear the site was headed in a different direction. Not better, not worse, just different.

DS: Why is it that I never heard of Deadspin until March 1, 2006? Which reminds me, how did you discover Lazy Tuesday? Kentucky Sports Radio, right?
WL: I think that's where I saw it, yes. And sorry you hadn't heard of it before then: We didn't have much of an advertising budget.

DS: How many times have you watched it since it came out?
WL: Twice? Three times maybe. Three times sounds right.

DS: Remember that time I accused you of being a Cubs fan? I'm glad I was wrong. I feel guilty of accusing you as such.
WL: You are forgiven.

DS: Were you always a Cards fan?
WL: Yes. I can't imagine anything else. It makes me sad to think of me cheering for someone else.

DS: I'm sure October 2006 was a fun feeling compared to the two years before. Shocking the experts was fun. Hell, MLB even was plugging the Mets as the 2006 NLCS winners. I still have that graphic somewhere.
WL: It was really quite great.

DS: We are one month into the 2010 Major League Baseball season. Brad Penny is looking red hot. Are you liking that acquisition right now?
WL: I am, quite a bit. Plus, I like baseball players that are in worse shape than me.

DS: Between Roy Halladay, Tim Lincecum, Chris Carpenter, and Adam Wainwright, who wins the National League Cy Young?
WL: Gotta think Halladay. He just torched my Cards again. I'm pretty tired of losing to the Phillies, by the way.

DS: Buzz Bissinger criticized you during a 2008 episode of Costas Now. Why?
WL: I think he thought I represented the entire Internet. I don't.

DS: Was it awkward to be sitting next to him during the special that aired soon after the 2008 All Star Game?
WL: Only when he put his hand on my leg. (He did not actually do this.)

DS: Jeff Labrecque of Entertainment Weekly gave it an A- in the May 7, 2010 issue. That has to feel good, right?
WL: Definitely. I grew up reading Entertainment Weekly, and to be reviewed by them was a real thrill.

DS: Did you ever date a Cubs fan?
WL: Yes. It didn't end well.

DS: What ended up happening?
WL: She murdered my whole family. (She did not actually do this.)

DS: Where were you during the Steve Bartman catch and what was your initial reaction?
WL: I was very, very happy, watching the game at a bar below my apartment, to see that the Cubs weren't going to the World Series.

DS: Thanks again for joining us. Anything else that you would like to add? Other than buy your book and the Chicago Cubs will never win a World Series.
WL: Both of those things sum it up quite well.