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

by 8 years ago

The greatest universal tradition of America’s pastime isn’t hot dogs, crackerjacks, or snagging  homeruns in the outfield bleachers. It’s b*tching, according to Will Leitch. “One of the great, grand traditions of baseball is b*tching about things that are wrong with baseball. That’s as much of a tradition as enjoying the game.”


If you’re a baseball fan and you spend many an hour in the sports blogosphere, you’re probably very familiar with Will Leitch. He’s the founding editor of Deadspin, the behemoth, take-no-prisoners sports and miscellany blog notorious for publishing drunk photos of Matt Leinart and dishing about Chris Berman’s “You’re with me, Leather” hook-up stories. Leitch’s also the guy who chickenshit author Buzz Bissinger tried to peg the downfall of humanity on in an anti-blogging tirade on a 2008 episode of HBO’s “Costas Now.” (Will, also onstage, fought back admirably.)


Besides a team-by-team spring training preview and a poignant tale about a drunken e-mail he once rattled off to Roger Ebert during his college years, the editor emeritus doesn’t write much for Deadspin these days. As a contributing editor at New York magazine, he co-edits “The Sports Section” on and writes long-form sports features and other profiles for the glossy. All that plus Leitch recently published his fourth book, “Are We Winning?”, appropriately sub-titled “Fathers and Sons in the New Golden Age of Baseball.”


With the 2010 baseball season in full swing, and Father’s Day less than a week away, we knew we had to not only get our hands on the book but also get Leitch on the phone.


“Are We Winning” revolves around a late-season Cardinals vs. Cubs game at Wrigley that Leitch attended with his Dad, a fellow Cardinals fan, and his best friend from the University of Illinois, a Cubs fan. The game recounted in the book takes place in 2008, just before the Cubs managed to secure their second NL Central title in two years. As Leitch is quick to remind me now, “In a superficial kind of sense, that’s kind of the last time anything good actually happened for the Cubs.”


It almost goes without saying that Leitch is a die-hard Cardinals disciple who takes communion at the alter of Albert Puljos. Leitch despises the Cubs “in a tongue-and-cheek-way” and begins jabbing Cubs fans with the much-scorned “lovable loser” stereotype in the early pages of the book.


Yet, despite team allegiances and lighthearted trash-talking, “Are We Winning” isn’t just about baseball. As the on-the-field drama heats up at Wrigley, Leitch riffs on larger themes of family, fatherhood, and new-found mortality by peppering each half-inning chapter with father/son anecdotes, colorful drinking stories, and sharpshooting commentary exploring the bigger issues in baseball culture. “Whether it’s the cocaine era of the late Seventies and early Eighties, Pete Rose gambling on baseball, the 1994 players’ strike, or the surge in players’ use of performance enhancing drugs, these ‘scandals’ have happened during periods of baseball growth,” Leitch explains.


Perhaps more importantly, Leitch stands up to condescending football fans and overly nostaglic, history-obsessed baseball romantics. He reminds both baseball lovers and haters that the game is just as monumental as it’s ever been: “You want to know what baseball’s golden age is? It’s right now. It’s this very second. There are more people watching baseball right now than any other time in human history.” 


I caught up with Leitch this past Memorial Day weekend about an hour before his beloved Cards took the field at Wrigley against the Cubs. We chatted about “Are We Winning” during his so-called “last bachelor drive,” from his hometown of Mattoon, Ill., to Georgia, where he got married the following Saturday. Two days before our conversation he was promoting the book in Chicago. (Married and back in New York, he’s reading at the Upper East Side Barnes & Noble tonight at 7 p.m.) What follows is part one of our discussion. Check back tomorrow for part two.


BroBible: Was this trip to Chicago your last bachelor hurrah?


Will Leitch: Uh, I don’t know. It was fun to get up there. The book event was the Friday night before Memorial Day, so I was impressed the place was packed. It was a pleasant surprised. With it being Chicago, I was afraid people would be mad at me. But I think any jokes I have about the Cubs are hopefully tongue-and-cheek enough that everyone knows I don’t actually hate the Cubs.


So no death threats from Cubs fans or anything like that?


No. I think if I was a Red Sox fan writing about the Yankees, or a Yankees fan writing about the Red Sox, maybe that would happened. The Cubs-Cardinals rivalry is kinda fierce, but it’s fierce in a way that nobody actually hates each other. I like to think of it in a way like the old Looney Tunes cartoons where Wiley Coyote and the sheepdog would sort of check in together in the morning before they beat the crap out of each other all day. They’d check back out and kind of shake hands and go home. I feel like that’s how Cardinals and Cubs are. They hate each other, but — if you really love baseball, no matter what team you root for — you’re pretty much on my side, so I can’t hate you too much.


The entire first part of the book is basically defense after defense in stating a case for baseball. Why do you think baseball needs to be defended right now to the rest of the sports universe?


I think baseball often needs defense from itself. One of the great, grand traditions of baseball is b*tching about things that are wrong with baseball. That’s as much of a tradition as enjoying the game. You name the generation and someone is complaining about how baseball is not as pure as it’s supposed to be. I kind of like that. I think it’s fun because it inevitably becomes like a redemption era; every time baseball is down, something comes and brings it back up again. I always find it to be kind of funny.


Certainly there’s this notion that football is America’s game and baseball is a game who’s time has passed. The facts don’t really bear that out. I think the reason that football generally gets better television ratings is that it requires less concentration on the whole. It’s a little more reality television than baseball is. I think that it’s less of a defense and more of a reminder that baseball is absolutely fine, because baseball’s a sport that’s obsessed with its past.


I’m certain that in 35 years, I’ll be like ‘Do you remember when we enjoyed baseball without the rocket packs’ and all the weird things that will happen in baseball in 2040. But, I think that’s part of the tradition. I think the reason that there’s this storyline that baseball is somehow past its day is mainly because most of the people who are covering sports grew up where they fell in love with baseball as a kid, and everything could do no wrong; Pete Rose was an All-American hero and all these wonderful things were happening.


When people realize that the people who play baseball are actually human beings, with all the flaws involved with this and that, I feel like it inevitably becomes some sort of defense of youth. When you think about it, it’s illogical to be a sports fan. It makes no sense. You’re rooting for a bunch of millionaires that don’t like you or care about you and are playing for a global corporation

that just wants your money. It doesn’t make any sense! I think that people try to come to terms with that by saying, ‘Well, the game was better in the past.’ The game wasn’t better — they wanted your money then too and they were millionaires that didn’t care about you then, too. I think that the most logical thing for a fan to do is recognize that our experience of viewing the game and experience the game is an entirely different thing than what [players] are doing playing the game.


I think if you can accept that and not be like, ‘Those guys are overpaid’ and ‘Those tickets are too expensive’ — even though all of these things are true — it doesn’t take away from the experience of enjoying the game.


You’re a die-hard Cardinals fan, but you’ve made the point over and over again about the book being a book for Cubs fans. Why so?


W: Well, (A) I hope it’s not just a book for Cubs fans. I hope that a fan of any team can understand the experience of being a fan and what goes into your favorite players and so on. Two, in a superficial kind of sense, that it is kind of the last time anything good actually happened for the Cubs. I tried to capture that feeling when the Cubs clinched the division in 2008. That was the happy time. Everybody thought they were winning the World Series that year, myself included. I had the vibe that it was 100 years, that team had been dominant all year, they appeared to be very set up, and there were no bad vibes on that team. I think there were some bad vibes on some of the Cubs teams earlier in the decade; there were some players that clearly didn’t get along. This was a likable team, likable players, likable manager, it just seemed to all be setting up for that to be the year. The book ends before the sweep in the playoffs, so in an alternate universe you can actually pretend that they did go on to win the World Series!


Ha, in a “Lost” universe.


Exactly — in a flash-sideways. Generally speaking though, I certainly think there are so many rips — playful hopefully — on Cubs fans. I would hope a book written like this by Cubs fans would have playful rips about Cardinals fans. I love the idea of rivalry and I grew up in an area on the border that thrived on that rivalry. In St. Louis, everybody thinks that Chicago is a foreign land, and in Chicago, everyone thinks St. Louis is a foreign land. So where I grew up, I’m right on the border of where there’s Cardinals fans and Cubs fans. I’ve pretty much been having this Cardinals-Cubs fans battle since I was five.


I’m kind of like someone who’s made really bad, racist public statements who has to do the ‘Oh no, I have lots of black-friends!’ situation. I have lots of Cubs fan friends. I do, I swear to God! I do not see them and light them on fire on sight just because they have a horrible franchise. My friends are Cubs fans. I swear, I swear!


Why the title “Are We Winning?”


We had trouble finding one for a long time. As usual I have no business doing anything with the title at all. I wanted to call it “It Gets Late Early.” I think it touched on the themes of a baseball game with the idea that you fall behind and, the next thing you know, it’s the sixth inning. You realize the end of the game kind of got here faster than you’d like. It also touches on fatherhood and mortality, which are some of the themes the book touches.


They said you don’t need this weird, esoteric, strange title, which I thought was incredibly fair. They came back with something that was a lot worse than that. I think they wanted to call it something like “Nine Innings with Dad.” One of them, I hope-jokingly, said, “Why don’t you call it, ‘I Love You Dad’? I said, ‘I’ll tell you what. If you locked that book in a nuclear silo, locked my father in a nuclear silo, and promised not to let him out until he or I are near death, then you can call it that. But other than that, no!’


So finally, the guy who came up with the title was Drew LaGuerri from Deadspin. I was really struggling and he actually came up with the title. He’s gone through the book thing and writes ad copy in addition to writing for Deadpsin, so I guess he’s good at bullshitting. So, he’s really good, and came up with a list of titles. The only problem with “Are We Winning?” is that if you don’t know anything about what the book’s about, you might think it’s a book about the “War on Terror.” It’s definitely not a book about the “War on Terror.” I am not qualified to write a book about the “War on Terror.”


Has your Dad actually read it?


If he has, he has not told me so. This is my fourth book and Dad hasn’t read any of the first three. I think that, certainly when I was writing it, it definitely helped that I knew that he probably wasn’t gonna read it. And it’s not because like he doesn’t like me. He’s just not much of a book reader. If he read it, I could be certain he would not tell me so, which is exactly what I would want him to do. When I was at church with my Mom this morning, three or four people came over and were like, ‘We read your book. Your father must be so proud.’ I was like, ‘By God, don’t tell him!’


My Dad came out for my bachelor party and my book party a month ago. He was on a plane going back to Indianapolis and, as luck would have it, Tommy Craggs, who writes for Deadspin, happened to be on the same flight flying back to Indianapolis. He texted me and he’s like, ‘Hey, you’re Dad’s on the flight. I think he’s got the book.’ I was like, ‘For God’s sake, get it away from him! Jesus Christ! Get it away from him, throw it out the window! Open up the escape door and just toss it out!’ So, as far as I know he hasn’t read it, and if he has read it I don’t want to know.


One of the things that really stands out is the entire chapter where you just publish your score books…


Yeah that was originally A LOT longer.


Why was that important to include in the book?


That was not really important, in retrospect. For the paperback, I might write a new chapter for that one. I realized that, I think it’s kind of fun because if you are the type of nerd that keeps a score book, you love that chapter. But there a very few nerds like that, and basically what happened was originally when I got the idea to do the book, I had no idea it was gonna be about my father or anything. I just wanted to write a book where I went to a game and each half inning said something larger about baseball, life, and so on. I like that about baseball — that every half inning is different than every half inning that’s ever happened.


So, I went to a lot of games that year. I went to freaking Tropicana Field that year looking for a good game, but I couldn’t find anything. I was just desperate by the end of the year. We lucked out this game happened to pop up. Because I do keep these score books, this is one of the chapters I knew I wanted to do. I love the idea that in 40 years I’ll show my grandkid a score book from 1998 with Mark McGuire and Sammy Sosa. Of course, he won’t give a shit, but it will mean a lot to me. At first, I thought it’d be a lot of fun to play with the idea of maybe doing a little thing from each score book. Then, once I realized, ‘Jesus Christ, I’ve been to A LOT of freaking baseball games,’ it ended up being an entire chapter.


I did every game originally and the chapter was like half the size of the book. It was a mess. So, if you think that chapter’s painful now, you should have seen how long that chapter originally was. It was very long. I think that of all the chapters, that is without question the most self-indulgent. If you look at the end of the chapter, there’s a note to my unborn son that says, ‘Listen, Dad doesn’t care if you skip a chapter once in a while. Thi

s is one that’s O.K. to skip.’

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