Part IV: Featuring America's Favorite Sports Fella...Bill Simmons



Part 4 of our celebration of all things Leitch begins with a very, very special guest. He just got finished celebrating the Celtics' 17th world title. I can't wait to see it mentioned 83 times in one of his NFL columns 30 years from now. It's Bill Simmons. It really is.

Bill Simmons:

Young Will,

Here's when I knew you had the sports blogosphere by the balls: When you gave a soccer column to an editor at Harper Collins, then that same editor signed you to a book deal ... and nobody made a big deal about it or brought up the blatant conflict of interest. That was amazing.

But it wasn't the only memorable thing about your Deadspin reign. You saved A.J. Daulerio from a career in amateur porn. You made Dan Shanoff, a heterosexual male with a wife and kids, actually go gay for you in print. You directed 500 of your minions over to ESPN.com's brand-new Conversation boards so they could make jokes about Harold Reynolds banging my wife. (Note: I didn't think this was funny at the time ... now, I have to admit, it was kind of funny.) You were described by Buzz Bissinger as "Jimmy Olsen on Percocets," an analogy that gets more amusing every day. You even turned Chris Berman into the Casanova of the 21st century.

And then there's this: Every time I got an e-mail from you for three straight years, I thought to myself, "Holy shit, I hope I didn't do something stupid" or "Holy shit, I am fucked." Then I'd read the e-mail and it was always something harmless like, "Sir, just a heads up, we're posting a photo-shopped picture of you deep-throating Tom Brady." So you should be proud. You put the fear of God in me on a daily basis. You also used the word "we" all the time in your posts, only you were always talking about yourself. What literary device was this? The fourth person? The fifth person? We always wondered why you did that. And by we, I mean me.

Only one thing truly bugged me about the Leitch Era on Deadspin: Any time you did a post about me, you always managed to pick the worst possible photo and enlarge it as big as you possibly could. For years and years, I wondered why you kept doing this to someone you allegedly liked. Were you jealous of my handsome looks and winsome demeanor? Was it your subtle way of bringing me down a notch? There had to be a reason. Searching for answers recently, I went on Google Images and found the following pictures of you. And then it all made sense.

Picture No. 1: This looks like June '93 cover of Molested Altar Boy Monthly.

Picture No. 2: "Wow, you caught me right as I was typing! I wasn't expecting you to snap this picture at all!"

Picture No. 3: What the fuck is happening here? It's like the cover of a bad Ryan Adams CD or something. I just picture the Harper Collins PR team showing David Hirshey this photo and him saying, "Oh, yes, it's brilliant, it's just brilliant!" right before sipping from a drink with a tiny umbrella in it.

Picture No. 4: I gotta be honest... I can't begin to figure out what's happening here. Does your digital camera not have a "delete" button on it?

Picture No. 5: Can't make fun of this one when it's been such useful porn for Shanoff.

Picture No. 6: If a picture can say a thousand words, then this one says eighteen: "I'm out of jail, I didn't mean to kill her, and I hope we can all move on."

Picture No. 7: Whoops, that's a picture of the girl who played Jo in "Facts Of Life." My bad.

Picture No. 8: Never has one photo summed up the title of a book better.

Picture No. 9 This photo ranks up there with the wacky Gooden/Strawberry/Tyson photo and every other weird photo of people who don't quite belong together. I'm trying to seem happy and might be drunk; you look like you're hoping the picture gets taken as quickly as possible before you're arrested. Actually, you look like that in every photo.

Anyway, I finally understand why you posted so many unflattering pictures of me ... you were trying to divert everyone's attention from your bizarre body of work on Google Images! I'm onto you, Leitch! Once you get acclimated at New York Magazine, I hope they teach you how to pose for pictures like you're not posing for a celebrity mug shot, a hostage photo or a soft rock album cover.

Best of luck with your new gig, God speed and may you as always refer to me as "sir."