In a Flash-Sideways Universe, the Chicago Cubs Always Win: An Interview with Will Leitch—Part Two

by 9 years ago



Two years ago, Pulitzer Prize-winning journalist Buzz Bissinger blew a gasket on HBO’s “Costas Now.” Will Leitch, editor emeritus at Deadspin, went from being a fellow guest participating in an on-air forum about “Online Media” to Bissinger’s verbal punching bag. The distinguished author of “Friday Night Lights” treated Leitch as a scapegoat, venting his frustration about the rising prevalence and mainstream media acceptance of sports blogs. Looking back two years later, the on-air sparring match was a classic generational clash between old media types vs. news media types: Bissinger’s childish, pompous rants about sports blogs snagging readers from the sports section of newspapers were akin to Walter Sobchak shrieking “This isn’t Vietnam. There are rules!” in a bowling alley. Leitch, fighting a difficult triple threat against an allied Bob Costas, Braylon Edwards, and a very agitated Buzz Bissinger, defended his position about an enterprising generation of online sports bloggers who “don’t sit in the press box.” 

Yesterday we published the first part of our conversation with Will Leitch, who’s on the offense promoting “Are We Winning? Fathers and Sons in the New Golden Age of Baseball.” After the jump, we discuss why he hates interviewing athletes like Derek Jeter, LeBron coming to New York, and whether or not he actually sent Buzz Bissinger a copy of his book.


BroBible: I noticed you have Buzz Bissinger in the acknowledgments. Did you send him a signed copy?


Will Leitch: I actually did! I actually just sent him one. It’s funny because certainly we’ve talked since the HBO incident, and I wouldn’t say that we agree on everything just yet, but I think that he certainly has a better understanding that I am perhaps not, you know, the Internet.


I think he may understand that I am not actually the physical manifestation of that, which is maybe a step above where he was that evening. But you know, Buzz is such a good writer. I love “Three Days in August,” his book about La Russa, and “Friday Night Lights,” which is obviously an incredible book. People forget he’s written so many good stories. You know the movie “Shattered Glass”? He wrote the Vanity Fair story that movie was based on. It’s just a terrific story. Before I got yelled at by Buzz, I always saw Buzz as the pinnacle of really great long-form journalists, so certainly I admire the guy.


There are times where I feel like he may be a little more hung up about what happened on HBO than I am, but I always joke whenever we e-mail. I think it’s like a little bit of a goal for both of us to sort of push that down in the obituary. I sent the book out because I was doing press for the book in St. Louis and ended up going on KMLX radio in St. Louis. They had a monthly book club where they have an author come on live on the radio for two hours. It was funny because it was in the morning at like 9 a.m. and everybody there was over 75. They were very sweet, but I was sitting there and Tony La Russa called in the first hour. He said he read the book and said that he liked it, which, the fact that Tony La Russa would read the book was a little bit terrifying. I think La Russa comes across fine in the book, but certainly La Russa’s a little bit more old school than I am.




Then, in the second hour, Buzz called in. It was really funny because it was the day that Buzz was on one of his Twitter rampages — always funny — and it was about the LeBron James story. It was like a 10-minute rant like about ‘I’m sick of what the blogs are saying! Will, I’m sure your book is great, we had our disagreement but your a talented writer, and everything’s fine, but seriously! All the blogs today have been going off lately about LeBron James!”


So he goes on for like 10 or 15 minutes on KMLX radio in front of these 75 year old guys that have no idea what he’s talking about. It was kind of amusing, so I did sent him the book. Regardless of the HBO thing, if Buzz Bissinger likes the book, I mean, that guys written a lot better books than I have, so if he likes it then I’m pretty flattered.


You’ve made somewhat of a career transition from being considered ‘the guy who posts pictures of athletes drunk’ to focusing on books and print journalism. How has the transition panned out?


Well, that still comes up. I did a thing on Chicago’s cute — and quite frankly better — version of “Around the Horn.” I talked on Comcast Sports where it was me and Dan Pompei, and their local TV guy, and I was on there.


It’s been two years since I’ve done Deadspin, and of course the first question they asked was “So do you like hire people to jump out of the bushes at these guys?” And I’m like, “For Gods sake, no one’s interested in anything thats happened in the last five years.” But certainly, you and I pay a lot closer attention to these kinds of things than I think most people,


To a lot of people, I will always be the guy who got yelled at by Buzz Bissinger or the guy who got rich off drunk athlete pictures, which is totally true by the way. Nothing gets you richer than posting drunk pictures of Matt Leinart on the web for free. That is like, “Wow, I’m rolling in it.”


I’ve written books and long-form post journalism pieces before Deadspin, during Deadspin, and after Deadspin, so I think there are people that don’t grasp that the world has changed. Someone can write for the web and also write for print and be just a journalist like everybody else.


When I started Deadspin, one of the main reasons I started doing Deadspin is that I’m a writer. The day after the Bissinger thing — this is a funny story particularly in retrospect — I went on “The Best Damn Sports Show” and I was on with John Calipari. It was awesome because Calipari really saw me as like this entrepreneur who had figured out a way to get rich on the Internet. It was hilarious. He was like, “Good for you man, good for you. Everybody’s got a gig man, you’ve found your niche, hang on to that.”


Calipari’s got like this weird vibe because he’s just telling you something even though he’s got nothing to tell you. He’s like “Good for you, man” and I’m like, “I’m just a writer, you know. They just give a little box and I just type in and I hit space and it goes to the Internet.” And he’s like “I know man, but you figured it out, you’re gonna grow from this.” And I was just like “Honestly?”


It was all kind of really strange, kind of like this odd notion that I got into Deadspin to get rich. I think it speaks a lot to the sports culture in general where everyone just kind of sees [the bottom line].


Sometimes I do have to go up and interview athletes for New York, which is still my least favorite thing in the world to do.


Why is that yo
ur lea
st favorite thing?


Why is that my least favorite thing? Because they’re not really very interesting. I mean they are interesting, but by design and by being smart they recognize that “there’s absolutely no upside for me saying anything interesting at all. Why would I say anything interesting?”


For the LeBron story we did for New York magazine, the last thing we needed was one more guy who had won a championship in New York to talk about why it was cool winning a championship in New York. We had Keith Hernandez, Mark Messier, and Lawrence Taylor. We had to cut him at the last minute. I don’t remember why… Oh yeah! I know, because that was the day he got charged with beating up a 14-year-old girl! So we were just like “Wow, I don’t think we can use this guy.” We even had this awesome quote from LT where he was like “Most of the stuff I did after winning the Championship, I don’t even remember! Hope I didn’t do anything bad. Ha. Ha. Ha. Ha. Ha.” Literally, the story broke the day we were doing that and we were like “Thank God it broke today or we would’ve looked like such a**holes!”


So I had to run up to Yankee Stadium real fast before the game, just to literally ask Derek Jeter this question: “What is cool about winning a championship in New York?”


A. This is a question Derek Jeter has surely been asked a million times. B. I know that this is not a particularly interesting question anyway. C. I was literally only talking to him to ask him this one thing. I’ve talked to Derek Jeter maybe twice. I wrote a 3,500-word feature on him, and talked to him for maybe 45-60 seconds. And it’s just dumb. So, I went up to him and was just like “Sir, I just have one question. What does it mean particularly to win a championship in New York?” He’s like, “Well that,s kind of a tough question.” I was like, “Wait, really? I don’t think it’s that tough, why?” He’s says, “Well, it’s kind of open ended.” And I was just like, “Well I could phrase it as a yes or no question if you’d like? I didn’t mean to have the notion where you’d even have to like think for a moment.”


But I don’t blame him! You know with a bunch of idiots like me coming by, you think of a guy like Jeter, who gets mugged by everybody, you gotta imagine he’s just like, “Fine everybody come in, stick your bun in the little pot of Jeter for a moment. Take away what you need, and then walk away.” That whole notion is just crazy. Sometimes in New York I try to like quietly prove that.


I’m really happy about the story I wrote about Derek Jeter. I think I wrote a story about Derek Jeter that praises Derek Jeter, but doesn’t blow Derek Jeter. And I was pretty happy with the piece even though I talked to him for about a minute. I like to think that I captured something about Jeter in my story that was a lot more different than like a Q&A 15-minute sit-down where he gets the same questions.


Of course he’s not going to give anything. I mean, it’s not like I’m gonna trick him. “Today I’m gonna get the REAL Derek Jeter.” No I’m not. Of course I’m not. No one’s seeing the real Derek Jeter today! Or, in a little part of his soul, in the like 15 million interviews he’s done in his life, he decided just to give it to ME today. So you know, I understand, in a general sense, why talking to athletes is important in a “How’s your leg feeling? Are you starting tomorrow? Do you want to be traded?” way.


I mention in the book that I had to do a feature on Nick Swisher. Nick Swisher is “baseball interesting” which is to say not actually interesting at all. And, he’s a totally nice guy, but there’s only so much I could hear him talk about Rascal Flatts. Like with my perspective on sports, I still wanna like sports, and I feel like a large part of that is keeping my distance from athletes a little.


What worries you about covering LeBron if he comes to New York?


Well one of the big advantages I have writing for New York is that it’s not a sports magazine, so it helps a lot because it lets me take different angles. If I want I can write a 1,500-word article about “Boy, New York sports media. These people are insane!” I don’t actually have to be on the daily beat and at the stadium everyday, so I can keep my distance. I know a lot of the guys on some of the teams, but I’m not really like a colleague of theirs, and I’m sure they probably see me as the guy who got rich off drunk photos of Matt Leinart instead of thinking of me as a colleague.


The fun thing about the LeBron story was I sorta wanted to get in the head of New York City and the Knicks and what the Knicks pitch would be. I thought that’d be a kind of a fun way to do it. I’ve got a lot more in common with Cleveland than I do with New York, so I like the idea of a piece about where he would live, where he would go out, and thought that’d sort of be a fun piece to put together. One thing that made me nervous is after [the piece was published], I talked to someone with the Knicks. He was like, “Hey man that piece came out well, are you gonna send it to him?” I was just like “Wait, we’re your plan? You gotta have a better plan than us! We have a 12-page magazine [article], you should have a 4,000 page …. and just send it to him for God sake!”


So if LeBron does come to New York, everyone has you to pat on the back?


Don’t blame me, man, don’t blame me. I am not taking responsibility. But I have to say, if LeBron James comes to New York, I don’t think he’s gonna be like “Wow, that 12-page paper sure did something for me. I wasn’t sure before, but that story about how much fun I would have in New York, that finally pushed it over the edge! O.K., let’s do it!” If that happens, then we’re all doomed.


So, let’s say “Are We Winning” goes on to fame and infamy on the bestseller list and lands you a very lucrative movie deal. You’re calling the shots. Who plays your dad?


I’ll do my Dad a favor. Let’s give him Clooney in 10 years. He could play him. I’m probably Michael Cera, which I’m very depressed to say. They’d probably make me Michael Cera. Or maybe the chick from “Twilight.” She could play a guy!


Perhaps she’s a big baseball fan.


Yeah, I’d be down with it. She goes the “Boys Don’t Cry” route. That’s how she wins her Oscar, as me! I’d say Kristen Stewert and George Clooney is probably the way to go.