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Ruby Dee died at the age of 91 on June 11, 2014.

June 11, 2016

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In February 2005, I was working for a magazine called Registered Rep. This magazine is still around; search its archives and you can even find some old features of mine. This one, titled, “Your Newest Rival: Your Firm’s Private Bank,” is utterly indecipherable to me now, more than a decade later. Registered Rep. was a perfectly fine trade publication, but I was a terrible financial reporter. I didn’t understand finance and, worse, I didn’t much care to: I have many interests in this world, but macroeconomics and estate planning are simply not among them. I would learn enough to write a specific story, and then dump it out of my brain the second the story was done. I didn’t understand finance, I didn’t care about finance, and I didn’t like talking to people who worked in finance. Definitely the recipe for stirring financial journalism.

Anyway, I somehow hung on to the job for more than two years despite never learning anything about the field I was ostensibly there to cover, but after a certain amount of time, I couldn’t fake it anymore. The Black Table, the site I did with Eric Gillin, Aileen Gallagher and A.J. Daulerio, had my full attention, and by the end, I was doing just enough to hang on to my job so I could continue to finance the BT. That inevitably came to a head, and by February 2005, Registered Rep. and I were sick of each other. The fun I was having with The Black Table gave me the illusion that I was a marketable writer outside of finance, so I told my boss, no hard feelings, but I think I needed to give my two weeks notice. I was gonna go freelance. I could make this work. And I couldn’t pretend to care about any of this shit anymore. He was nice about it; he liked me, and I liked him. But it was clear he was OK with bringing in a, you know, real financial reporter to replace me.

We went out drinking my last day, and I woke up that Saturday morning, to my surprise, in a considerable panic. It occurred to me: I had no job, hardly any money and, all told, a lot fewer professional writing opportunities than I had been pretending I had. I remember that Sunday vividly, heading to the Web cafe in Times Square — because I didn’t own a computer, in spring 2005, if you can believe that — and emailing everyone I knew, saying I was available, I was willing to work, I needed to work, I’m willing to do anything. Need any financial stuff covered? I covered finance for two years! It was clear I’d made a terrible mistake, leaving a full-time job, with benefits, and having nothing lined up. I was 29 years old, and terrified.

That Monday, out of nowhere, unsolicited, I received an email from Lockhart Steele, the managing editor of Gawker Media. He said he liked my work at the Black Table and wanted to know if I’d be interested in trying out for a gambling site called Oddjack they were launching. For reasons I still don’t understand — I’d just spent the weekend tearing my hair out, after all — I told him that I didn’t like gambling and thought it was bad for society, making me a terrible person to run their gambling site. But, I said with raised eyebrow, Gawker should do a sports site. Here, Lockhart, let me write you a memo explaining how it would work. After much discussion and haggling and arguing about nomenclature, six months later, Deadspin was born.

That call changed my life forever. It is not an overstatement to say that my life can be rather neatly divided between Before Deadspin, and After Deadspin. I’ve been gone for eight years, but it’ll still be the first line of my obituary. I went from an unemployed, failed financial reporter to someone who has been able to make a career out of writing for 11 years now. I owe that to Lockhart, and Nick Denton, and Gawker Media, and the opportunity available there that was available nowhere else. And of course my story is the story of many, many others, people far more talented and doing far more important things than I am. Gawker has made more than its fair share of mistakes. But if you think the world isn’t more interesting and isn’t smarter and isn’t a little bit more honest because Gawker Media exists, you’re kidding yourself. I don’t know what’s going to happen with this whole mess; I suspect Deadspin, and many of the other sites and other talented people, is going to be just fine. But at this moment of transition and peril ... I stand with Gawker.

Also, Lockhart Steele is now a reality television star, apparently.

Here is a numerical breakdown of all the things I wrote this week, in order of what I believe to be their quality. (This is an attempt to have an objective look at the value of my work in a way that I suspect will be difficult to sustain.)

1. America Disney-fied Ali Before He Died, Sports On Earth. I didn’t write about Ali until three days after he died, which is basically several decades in internet time, but I think it helped get to what I think is a fundamental truth with how we deal with the deaths of universally beloved people like Ali: We ignore what was once divisive about them — and what was divisive about Ali was what made him such a great man — in favor of vague platitudes to easily share on social media. The injustice that Ali fought is still going on today, but the Ali in the public imagination was separate, made almost angelic, from the issues he cared about so deeply. I know there have been a million Ali pieces, and many great ones, but I was happy with how this one turned out. Plus, it allowed me to go back to one of my favorite topics: How awful people are when a celebrity dies.

2. New Media Creates a “Never Trump” Zone, Bloomberg Politics. I hadn’t actually written anything for Bloomberg Politics for a while — it has just been podcasts for the past couple of months — but because I’ll be writing constantly for them from the RNC in Cleveland this year, I figured I needed to get back on the horse. Here, I made the argument that Buzzfeed’s decision to refuse money from Donald Trump and the RNC for advertising may have been less about Buzzfeed’s political views and more about the weird, hazy world of native advertising. Side note: Doesn’t it seem funny now that we once thought Buzzfeed doing journalism was somehow absurd? They’re one of the best news organizations going right now.

3. Warcraft, Bored of the Rings, The New Republic. A-plus headline, truly terrible movie.

4. Why Do We Keep Ignoring Jurgen Klinsmann, Sports On Earth. These are two things I deeply love — the USMNT, and making fun of helicopter parents — dancing hand in hand.

5. Cubs’ Success Raises Key Questions for Cards, Bucs, Sports On Earth. Dirty not-so-secret: I’d write about the Cardinals every freaking day if I could. Waino!

6. Pittsburgh Deserves the Chance to Win the Cup at Home, Sports On Earth. Seeing the Cardinals’ 2006 title in person, with my parents, remains one of the most wonderful experience of my lifetime. I think I’m still hungover.


7. Every Apatow Movie, Ranked Worst to First, Vulture. This piece, co-written with Tim Grierson, originally ran last year, tied to the release of Trainwreck. This time we added a capsule and ranking for Popstar. I wrote that capsule.

8. MLB Drafts Impact the Majors More Than You Think, Sports On Earth. A couple days later, to be honest, I’m not entirely certain I believe my own argument here.

9. I Ranked Lonely Island Songs, The Will Leitch Experience. Seriously, the Bin Laden song is just brilliant.

10. Guess Which Team Won This Baseball Poll, Sports On Earth. Go on, guess.

Two podcasts this week. As I say every week: If you are the sort to subscribe to a weekly newsletter, I would have to think it wouldn’t be too much of a hassle to subscribe to one of the four (!) podcasts I do. Here they are:

The Will Leitch Experience, talking with Alyson Footer about the AL West, the AL Central and the MLB Draft.

Grierson & Leitch, this week discussing “O.J.: Made in America,” “Popstar: Never Stop Never Stopping” and “John Wick.”

Culture Caucus, no show this week, we’re taping a new one Monday.

Waitin’ Since Last Saturday, no new episode, put we’re taping a new one on Wednesday.

I am going to drink heavily and scream for the USMNT tonight. (Make sure to tape Part One of “OJ: Made in America,” 8 p.m., ABC.


Have a great weekend, everyone.


Best,
Will

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