An IM session with Will Leitch concerning his new book, 'Are We Winning?'

I first met Will Leitch in person at a Mexican Restaurant in lower Manhattan in 1999. There were four of us there that afternoon, and I remember Will had the shrimp empanadas. Little did any of us realize that the kid with cilantro leaves on his tie and diced plum tomatoes in his lap would one day become the founding editor of pioneer sports blog Deadspin.com, and the author of four books. The latest, Are We Winning?: Fathers and Sons in the New Golden Age of Baseball, is a funny, moving and wise treatise on all of the above-mentioned things. It comes out May 4; available wherever fine jewelry is sold. You should buy it. I chatted with Will recently via IM machine, about the book, and why the Giants are better than the Cardinals, and always will be. Here are the results of that trial:
rickscafe: Is this thing on?
wfleitch is online.
wfleitch: Hello! I come to you live from my desk. The mood here is mirthful, with a side of gassy.
rickscafe: ha. Finished the book. Was the chapter on erotic massage really necessary?
wfeitch: Yes. I just hope it makes sense. It is very possible I told the same story four times, in different sections of the book, all with different details each time. Books are freaking huge. By the end, I was spelling my father’s name wrong. (I spelled it “Dyd.”)
rickscafe: well, the part about you and Neville Chamberlain was confusing.
wfleitch: Sorry the middle third is in Spanish. I don’t speak Spanish, but, you know, I thought it was worth it to wing it.
rickscafe: Have you been assaulted by any Cubs fans yet?
wfleitch: I’ve tried to tell everyone that this is actually a book FOR Cubs fans. I mean, the game I document is literally the last great happy moment Cubs fans had. Everyone in that stadium thought they were winning the World Series that year.

wfleitch: Including my father and me, and definitely Mike. It was the 100th year, everything was primed, Milton Bradley wasn’t there … it was clearly supposed to be the season it happened. It’s bizarre how far astray it has gone since then.
rickscafe: It seems like, in a way, you envy Cubs fans their pain and longing.
wfleitch: There’s a grandness to it that I admire, and it’s not all wrapped up in existential, pseudo-academic angst the way Red Sox were before they won it. The Cubs winning the World Series would be the biggest story in sports; it’s the only sports story other than a terrorist attack on a stadium that would be on the cover of every non-sports magazine, newspaper and website if it happened. With the Red Sox, you always sensed it would happen someday and everyone would be quiet about it. With the Cubs, after Game 6 of the 2003 NLCS, and after their postseason sweeps, you have to sincerely wonder if it ever will. There’s something very lasting and human about that. And Cubs fans don’t get dark about it. I think there’s more frustration in recent years than the past — when it was more almost accepted — but they also don’t get all dark about it. I think it’s because it’s nearly impossible to be too upset and morose at Wrigley Field.
wfleitch: Also, as a Cardinals fan, I find their losing cute. It’s just adorable.
rickscafe: Ha. An alternate title for your book could have been, ‘Shh, your father loves you. You didn’t hear it from me.’ I guess the big question is, how did your father react to the book? Has he read it?
wfleitch: Last I heard, he was 200 pages in, which is probably the farthest he has ever made it into a book, and that includes my first three. He’s actually coming out to New York for my bachelor party this weekend, and I sent him the book three weeks ago, hoping he’d just read it before he got here so we could have the following conversation about it:

Random person that’s not Will or Dad: “Hey, Bryan: Did you read Will’s book?”

Dad: “Yep.”

Will: “Yep.”

[both glaring at random person]

Random person: “I’ll be going now.”

wfleitch: And then we can be done with it.
rickscafe: Your mom’s reaction?
wfleitch: She said, “I’m glad it’s not about me.”
wfleitch: I tried to tell her it wasn’t about Dad either, that it was about all dads, and fatherhood, and baseball, but then she started telling me about my sister’s new boyfriend and I tuned her out. It’s hard to run PR on your mom.
rickscafe: Publisher’s Weekly called the book “loose-limbed and beguiling.” Your thoughts?
wfleitch: I think that’s a very nice way of saying, “Most of the books we read are more organized than this.” But I also like to think the book has a real narrative structure to it. I want it to be fun to read: I think too many people get caught up in the “Oh, man, I’m writing a book! I better make it BOOKY!” (Note: The correct word there is probably “bookish.”) I know I did that with “Catch.” One of the great things about writing for so many different platforms is that you really get to hone your voice, and you learn that whether you’re writing for the Web, a magazine, a newspaper, a book or a bathroom wall, it’s all pretty much the same thing.
wfleitch: Other word from that review I liked: “Jaunty.” It makes it sound like I was writing it while skipping down the street.
rickscafe: I picture you furiously crossing out words, mumbling “not jaunty enough.”
wfleitch: “Needs more jaunt.”
rickscafe: no pop-up illustrations, I noticed.
wfleitch: It’s a difficult time for the book industry. They bonged a whole bunch of my ideas. “Scratch and sniff.” “Scratch and listen.” “Look wee there’s a snake in your book!” “Special collector’s thermos edition.”
rickscafe: you’re right about the book industry. just this book’s existence is a big accomplishment.
wfleitch: It’s hard, particularly the way that I like to write them, which is to sell a publisher on an idea and then executing that idea — or completely drifting off-course from it — once the deal is signed. (I have the narcissist’s disease of being terrified of writing things no one will ever see.) It’s a credit to Hyperion how much work they’ve put into this book, because it’s not exactly an easy sell. A lot of the quick phrases people use to describe it — “father’s and sons and baseball!” — I think don’t adequately get across what the book’s about. I have that trouble a lot. I just hope people read it. It’s much more fun to write books than describe or sell them. I have no idea how people in the book industry do it. It’s the Lord’s work, really.
rickscafe: My guess is that each person who reads it will take away something entirely different. For me, the part that resonated most was your dad coaching your VFW team. That was really a book within itself. No portion of the book better illustrated his real character than those paragraphs.
wfleitch: It’s funny, because all that stuff about him being a great little league coach … I HATED it at the time. I was one of the best players on the team and was pissed off that he didn’t let me play every position. Didn’t he want to WIN?
wfleitch: My mom kept all those old scorebooks, and I looked through them a few years back. I wasn’t nearly as good as I remembered.
rickscafe: 5×5 (5 errors)
wfleitch: It’s funny, because I find myself, every time I talk about the book, trying to fight of the idea that it’s about “me,” or “my dad.” It’s really not. It’s actually more the spirit of the old Life as a Loser columns, the later ones, back when I was finally starting to figure out my voice a little bit. I’m just hoping that people recognize parts of themselves and these larger truths; my stories, and dad’s, are just my entryway into it. At least I hope so.
wfleitch: That was deep! OK, now let’s go back to jokes about robot hamsters.
rickscafe: wait, I think I actually read Life of Pi. Your book is next.
wfleitch: My next book will be called “Type. Read. Cry.” It will be about how I rejuvenated my dry, corporate life by writing a politics blog.
rickscafe: Well, the book was endlessly entertaining, and I’m not just saying that because I read it while waiting at the DMV. I hate the word cathartic, but do you feel as if a weight has been lifted, and you can now move on to other things?
wfleitch: Every time I finish a book, I always think, “Oh, man, that’s over, now I can relax and spend my days buying large hats.” And then I start feeling antsy about not working on another book. So I start another one. This is going to repeat FOR THE REST OF MY LIFE.
wfleitch: In other words, I need the book industry to fail so that I might live like a normal human being. Fingers crossed!
rickscafe: Thank you, Will, for taking a break from fighting crime to be with us today.
wfleitch: Thanks so much for doing this.
rickscafe: this interview will not appear anywhere; it was a deliberate waste of your time.
wfleitch: I’m fine with that.