Tommy Craggs Is A Prick Who Just Fails Upward

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Evidence supporting that fact begins here. This guy actually had the giant sack to put that word in a headline several months ago when something called Suey Park decided to go all Hashtag Amy Uyematsu after Stephen Colbert made a joke at the expense of Daniel Snyder. (Oh, you don't know who "Amy Uyematsu" is? Here's a link. Craggs would drop obscure cultural references in his prose all the time and become very frustrated when I didn't understand his comparison between Donald Fehr, former executive director of the MLB players association, to a German opera.) Predictably, the headline sparked even more outrage, mostly because, well, a person named Tommy Craggs can't pull off wry satirical commentary to defend other people's absurd satirical commentary. Maybe if his byline was Tommy Chang it would have gone over better. Probably not.

Let's start at the beginning: 2008. Deadspin was soon-to-be ruined because founding editor Will Leitch left for New York Magazine. The two people picked to replace him? Clay Travis and me. To be fair, Travis was actually chosen to be the incumbent EIC. I was simply there to smooth the transition between Leitch's Deadspin and whatever Clay had in mind. Nick and then-managing editor Noah Robischon were still unsure about the prospects of Deadspin post-Leitch, and decided that in order for the site to survive they needed a name with mainstream media cred to help the site reach whatever was considered The Next Level during that era. Clay Travis, then of CBS Sports, was on the shortlist. I was on the no-fucking-way-but-let's-be-nice-to-Will list. Another member of that vaunted shortlist was Grantland's Bryan Curtis. At the time he was working at Play, the Times' magazine's now dead "sports magazine" written by masturbatory smart people who like to write about sports because it gets them published in "America's Best Sports Writing" every year.


Curtis also declined the job, but he did rec his good friend and part-time Play contributor Tommy Craggs. Here's Curtis' recollection:

I told Denton, "He's the best sportswriter I know." Full stop.

Denton looked up from his device and said, "What's a sportswriter?"

Then he went back to his device.

I hope you get into how Tommy regards every promotion as his final moment of reckoning with the Peter Principle. After you guys were installed at Deadspin (and thank god for that), he repeatedly said how terrible he was going to be at blogging, how he was going to shit his pants in public, etc. When Tommy tells you he's going to fail at something, it's a signal he's about to do it better than anybody else. "


I'll get to that later. For now let's focus on the "how terrible he was going to be at blogging" part because it does require thorough examination: Tommy Craggs is, in my opinion, the best writer to ever work at Gawker Media. He was also the worst fucking blogger to ever work at Gawker Media.

About a month into our tenure at Deadspin, I sent then-managing editor Noah Robischon a very detailed memo outlining why I thought that Clay Travis wasn't a good fit for the site. He agreed with my assessment, but said I needed to begin the search for his replacement immediately before I could fire Clay. To help expedite the process, he sent me the Top Secret list of the ten best Deadspin EIC applicants. One of the first people from that list I reached out to was SB Nation's Chris Mottram. He said no. The second person I reached out to was SB Nation's Spencer Hall. He also said no. After those two rejected my offer there weren't many others who scored highly enough on Leitch's worthy-of-taking-over-Deadspin scale.

But there was this one other guy...

Robischon told me about this friend of Bryan Curtis named Tommy Craggs. Unfortunately, he turned his blogging test in on a half-assed Tumblr called — no joke — "Your Shoah of Shoahs." He also turned it in about a month too late.


Robischon confirms this account:

Everything you have is spot on. At first I thought you could not have been right about that Tumblr because it sounded so unbelievably terrible. But as you can see below that really was the name. Let me add that anyone applying for an editorial position who includes not only a P.S. but a P.P.S. in their email usually goes straight onto my no-hire list.


————— Forwarded message —————

From: Tommy Craggs

Date: Thu, Jun 26, 2008 at 6:44 PM

Subject: Re: Deadspin

To: Noah Robischon


I'm not sure if this is exactly what you're looking for, but I gave it the ol' college try.


P.S. It's my first dance with Tumblr, so if the formatting's a bit spotty that's why.

P.P.S. An editor-friend of mine says talking with me is like "caveat theater," as the above demonstrates.



Tommy's propensity for sling-shotting himself in the face when it came to career advancement is, as I would later find out, an ongoing trend. Still, I recognized his name. He was the dude that wrote that Stephon Marbury piece and that Joe Morgan thing. This guy was an outstanding writer and would completely fit into the long-term plans I had for Deadspin. Very early on during my tenure as EIC here, I'll admit, I thought I'd never be able to see that vision succeed and that Deadspin was doomed to fail. If that was the case, I wanted to kill it properly by hiring Tommy Craggs. It felt like the right thing to do.


During Tommy's first full-time week at Deadspin our interactions were fairly brief, but most of them went like this:

Me: How's it going?

Craggs: Am I getting fired?

Here's some more typical inter-office banter with my shiny new hire :

  • "I think I have a brain tumor" (His response to why he couldn't write one short post on a particularly light day)
  • "I have rage issues" (His response to how his weekend went and why was his hand all bandaged up)
  • "I just threw up in the sink in the office bathroom" (Unsolicited)

Between Sunshine Craggs and my own unorthodox style of management the "new" Deadspin was off to an inauspicious, inconsistent start. The one who suffered the most during those early Craggs days was Dashiell Bennett, who would often be the only person posting anything daily. I was working from home one day and asked Dash how Craggs was handling his second week in the office. He G-chatted me back something to the effect of "I think he's about to kill himself."


This went on for months: months of Tommy's great ideas falling well short of ever being executed; months of Tommy diagnosing himself with different undetected terminal illnesses; months of Tommy being convinced he was about to get fired. I fired pretty much everyone else at Deadspin — some beloved by many of what was left of Leitch's core readership — to clear space for Tommy Craggs. It wasn't entirely because I had some grand editorial vision anymore, but mostly because his peculiar brand of neuroses was consistently entertaining to me. Also, as a reader, when Tommy would get riled up about something and actually, finally, ya know, WRITE, it was just jaw-dropping. I started receiving off-the-record emails from various heavyweight sportswriters begging me to please, please let them know ahead of time if they'd pissed off Tommy Craggs. One of those I remember was SI's Chris Ballard. Another? Jason Whitlock. Deadspin wasn't just a mean-spirited blog anymore taking potshots from the peanut gallery. Not if Tommy Craggs wrote the post. The best in the industry knew that if Tommy went in on ya, he'd go in hard, and that shit would hurt.

Even if I got one post per month out of him I was convinced it made Deadspin better than anything else out there at the time. I'd often bully him into writing ridiculous throwaway posts unworthy of his freakish talent in the hopes that he'd understand that his contributions, no matter how mundane, were always welcome. This one titled "Mutton Wins Again," was one of the first punishment posts I assigned to him. "This is so so stupid" was his typical response to me after he'd spend half the day crafting dum-dum shit like that.


At one point his inability to write more than two or three times per month became so problematic that I resorted to lame-ass motivational management techniques. I even bought him a Moleskine notebook and encouraged him to use it everyday to help better organize his thoughts. He took the notebook, sighed, muttered something to himself about being a failure, and hung his head in shame. During those early months, I think he wished that I had fired him. If I just pulled him aside and told him "you're really not cut out for this" I would have, at the very least, given him some respite from his crippling self-loathing.

I know that this is supposed to be a roast and I have many, many embarrassing things I could tell you about Tommy that would probably mortify him. But most of those incidents were also instigated by me so it wouldn't be fair to pin all of that on him. Instead, I'll just apologize for some of them:

  • I'm sorry I made you keep a running list of who on the Jezebel staff had the smelliest shits.
  • I'm sorry I gave you ecstasy and told you it was "adderall" at many of those Deadspin meet-ups and then left you reeling all by yourself to figure out what happened in front of complete strangers.
  • I'm sorry I made you try mushrooms for the first time at The Terror Museum in Budapest.
  • I'm sorry I made you sit next to the designated office-crap bathroom and poop-smog you everyday. ("Poop-smogging" is when I would enter the crap bathroom, break the deodorizer in half, roll it out the door like a hand grenade, leave the door open just a crack, do my business, then completely stink up his workspace.)
  • I'm sorry I told Jessica Coen about how you used an Oakland A's plastic cup to dispose of your jizz after you masturbated.
  • I'm sorry I told Nick your name was "Drew" in order for him to say hello to you.
  • I'm sorry I said you looked like a "fat Easter bunny" when you would wear that awful pinkish-colored Polo during the first warm Spring days.
  • Actually, I don't think I ever told you that to your face but, hey, sorry for bringing that up right now.
  • I'm sorry I would dump your Viagra pills that you'd order on your keyboard and announce what they were to the whole staff
  • I'm sorry I'd fart on your unattended mozzarella sticks while you were away from your desk.
  • I'm sorry I would steal some of those Viagra pills and the charge you for them anyway.

The only thing I won't apologize for is constantly setting you up to be a huge failure on a larger scale. Now that you're in charge of Gawker Media's entire editorial future, I feel, once again, it's my duty to reassure you that you're really not cut out for this. I'm sure you already know that, but do it anyway. You've always done it right.