In early 2001, I was middling through a job at Thomson Financial Media as managing editor of "Health Care Finance" magazine. It was a quarterly publication, which meant plenty of downtime. It was during these extended lulls, reading MediaBistro, that I stumbled upon the ongoing unemployment saga of one William F. Leitch and his "Life As A Loser" series. MB did an item about one of Will's columns, "He Hate Me", where young William spoke of his time as a media news aggregator for Brill's All-Star Newspaper, a mindless, Romenesko rip-off site-job that had absurdly garnered him an anonymous email stalker named Grady Olivier, who would pepper Will's email box with brilliant daily reminders of Will's consistent awfulness:
....We'll begin today with your overreliance on the colon. Please provide a compelling rationale/rationalization for your need to use one every third sentence. Also, why did you hyphenate "front line" in the pull to the Ian Fisher piece? "A pair," as in the Levin bit, would properly take the third person singular. You misspelled "government" in the Pomfret lead, you melon-headed motherfucker. There's also the issue of your questionable comma usage in your intro to Mr. Hiaasen's piece of February 28...Please resign your tenure as early as possible, making sure to apologize to Mr. Brill for your gross stupidity when collecting your severance.
I was hooked. At that time, I think I was more drawn to Grady Olivier's well-crafted insults than the overwrought, meandering columns of this weirdo Midwestern rube who seemed to complain about everything -– mind you in a genuinely, folksy, likable manner -– but I came around. I began reading his column at Ironminds every week, then began to rely on them, and then became obsessed. I'd also, thanks to Will, started writing my own columns for Ironminds. But soon after my interest kicked in to high gear, Will up and quit Ironminds. (Will's successor at Ironminds was a fella named Rick Chandler.)
After Will left Ironminds, he dropped out from the writing world because, in his mind, it wasn't getting him anywhere, regardless of his hundreds of loyal fans who read him. He was broke, and he wanted to grow up. We had a mutual friend, Aileen Gallagher, and after about three months of not hearing about what Will was up to, she finally told me that he was now working at a doctor's office in midtown, answering phones, and "trying to be a human being again." That was the party line from Will that she was parroting for him.
"He's not writing at all? " I asked.
"No, he's taking a long break," she said.
This gave me an idea: Why not help Will get back into writing and offer him a freelance job for Health Care Finance magazine? I did, and after about a week of considering it, Will emailed me back and said he'd do it. He'd call me later that day to discuss the details of the story and he was grateful for the opportunity to make extra money anyway he could. We were off.
Now, up until then, I'd only had one 45-second conversation with Will at a mutual friend's birthday party, where I complimented him on his column, and he blew me off with the courteous disdain of a rock star being propositioned by an overweight groupie. So, when he called me at the office that day, I was taken aback by his freewheeling stammer and how overly polite he was to me on the phone.
"Mr. Dah-lorio, this is Will Leitch…." (Will has, to this day, still never once pronounced my name correctly. It's DAH-LAIR-I-O. Thanks for asking.)
From there we set deadlines for August - a month from then - a pay rate, and the expectations. Will assured me that even though the subject matter wasn't interesting, "he never missed deadlines." About a week after our initial conversation, I received another phone call from Will, who was, again, overly polite, and kept referring to me as "sir," but he got to his point rather quickly.
"What exactly am I writing about again?"
To be fair, the story about hospitals outsourcing some of their help to foreign workers via H1B visas was cumbersome, and it was more telling about how boring the job was than how irresponsible and disinterested he was. I explained to him exactly what he needed to do, who he needed to call, and forwarded him every article I found that wasn't loaded with municipal bond financial terms that even I had yet to fully grasp.
He said he understood, assured me that this would make it 10 times easier and once he finished all the research, "the writing would be the easy part."
I know, I thought. I trust you. You're Will Leitch, for God's sake.
Another couple of weeks went by and Will had finally turned in a draft. Writing-wise, it was fine. However, it was still written like one of his columns, the "Hey, I'm writing about something I know nothing about – so let's make this fun!" variety.
I enjoyed it. My editor did not. He would need to do a re-write. This is when the editor-writer relationship between Will and me became bizarre. Communicating with Will the day the second draft was due became complicated by the fact that, for some reason, his email account at the doctor's office was not working. I knew this because I began receiving strange emails from names I did not recognize -– MIchael-something -– was the most common one.
"Hey, it's Leitch… email is down. I'll be using this account for a while."
Somewhere along the line, the "Michael" email went down too. I found this out because I'd received an email from Will's girlfriend at the time, a woman I'd never met, much less communicated with, informing me that she would be giving me updates on the story's progress the rest of the day. She was also overly formal.
"Mr. Daulerio: I'm Will's girlfriend. Will wanted me to let you know that he's having email trouble but would get in a draft at the end of the day…"
Of course, this was odd, but it was humorous. I responded to her joking that she should reconsider the relationship since he can't seem to keep his crap together. I didn't expect a response, but I got one anyway - a 500-word, all-caps screed which said I was absolutely right to think she deserved better.
"HE'S A FUCKING LITTLE BOY, " she said and "IF HE JUST FINISHED HIS NOVEL, MAYBE HE COULD AFFORD TO BUY BEDSHEETS." She went on to say how pathetic his work ethic was and that she was tired of "PICKING UP THE SLACK."
"HE'S NEVER EVEN TAKEN ME OUT TO DINNER. NOT ONCE!"
I wanted to pull Will off of this story because it seemed this was more of a headache than it was worth. Fan or not, I had to keep my job. But Will called, sincerely apologized for the melodrama, and said he'd turn in a draft as soon as he could, once things settled down a bit. Weeks went by, again, and there was little or no progress on the story-front, but Will and I had become friends during the whole ordeal. So, at least that had worked out. Then, one gorgeous September morning, Will decided it was time to get serious about the H1B visa story. He'd been reinvigorated and was ready to tackle the reporting head-on and stop messing around. His timing for such a revelation could not have been more impeccable:
From: Will Leitch [mailto:email@example.com]
Sent: Tuesday, September 11, 2001 9:05 AM
To: Daulerio, Albert
Listen, you're going to have that story all polished up and ready for you first thing tomorrow morning. I apologize for the delay. Getting back on top of things now.
I'd like to say that after this incident, this is when Will woke up, got his shit together and proceeded to take off on a comet-like trajectory toward writing stardom. It was not. Most of his friends in New York have seen him, in his late 20s, live for weeks on pocket change and subsist on a steady diet of "free apples at work" and old pizza that would make even the most destitute of college freshmen pity him. He once went five years without purchasing a new pair of shoes. He insisted that, even though the soles of the ones he wore every single day could be peeled back to the heels, they were perfectly fine. (Some days, it would sound like he was wearing scuba flippers.) He has lived in basically every far-flung borough in New York City, chasing cheaper rent and still blissfully, ignorantly chasing a dream.
Do not for one minute think that Will's job at New York magazine was given to him because of his Deadspin success - he was hired in spite of it. He works tirelessly at his craft. He takes pride in every piece he does, regardless of pay rate or circulation size. And, of course, he never misses deadlines.
Oh and that ex-girlfriend? Yes, she was mercilessly cruel. She treated Will horribly and made him acutely aware of his shortcomings and imperfections. She made him him feel constantly paranoid about his place in the world. She made him feel like an ugly, loathsome human being.
But that still didn't stop me from drunkenly hooking up with her one night soon after they broke up. Sorry, dude. She was kinda hot.
See you Monday, everybody…