I've had the privilege of sitting next to Craggs for five years now (and working alongside him at ESPN The Mag for a year before that, though I don't think he once bothered to say hello or introduce himself—this generation's I.F. Stone wouldn't deign to pretend he was doing anything more than slumming as a fact-checker, and that means avoiding mingling with the drones) and I've learned that he is, at heart, a big, cranky sack of shit, and probably couldn't function any other way. He feeds on his own stress. He wallows in self-pity. He thinks having more than one thing at a time in his to-do pile makes him a martyr. He growls, out loud, like an animal, when he's feeling particularly grumpy. If you call him out on his performative angst, he will theatrically swipe a stack of books from his hoarder's nest of a desk onto the floor.

This would all be fine if he kept it to himself; it's how he works, and it's clearly served him well enough to trick Denton into thinking he's a tortured genius as opposed to a run-of-the-mill masochist. But the secret to working with Craggs is that he's not content just being unhappy. He wants to drag everyone around him down into his shitpile.

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  • Craggs would regularly take the staff out for drinks at the usual place (A.J.'s place, actually; real original). The whole time, he'd be sure to remind you how much this was costing him. Bills could easily hit $1,000, and he'd moan and bitch and you'd feel bad and offer to throw in your share and he'd say "don't worry about it." And then you'd talk to any other site lead, and they couldn't understand why Craggs wasn't getting reimbursed by the company for what clearly qualified as work outings. And then you'd see Craggs's pile of receipts dating back months and months, and you'd realize: the motherfucker was trying to make you feel guilty just because he was too damn lazy to fill out an expense report.
  • For a couple of years, Craggs sat next to the office's smaller, isolated "poop bathroom." He maintained, it was alleged, a poop spreadsheet, that supposedly kept track of who shat and when, and their relative smelliness. I never saw the spreadsheet, so I can't say if it actually existed, but I don't think it needed to; Craggs had his co-workers' shit habits memorized. "Three o'clock, every day" he'd mumble as Scott Kidder made his regularly scheduled shit visit. Craggs didn't keep his knowledge a secret, either. What's better than knowing your co-workers' shit habits? Making sure they know you know, and so can't possibly shit in comfort.
  • Don't ever play blackjack at the same table as Tommy Craggs. "It's the process, not the outcome," he'll mutter, chiding anyone who dares to depart from optimal strategy. Which would be one thing if Craggs appeared to be taking any joy from his robotic stimulus-response play, but he doesn't. He sits there, stares intently at the dealer's cards, and shows zero reaction whether he wins or loses. And yet he insists there's something intellectually gratifying about making the right decisions, at the expense of forfeiting your free will, even if it means you lose money. "It's the process, not the outcome." By the end of the Budapest retreat, everyone was calling him "The Process." He thought it was a compliment. It was not.
  • You think it takes a long time for Craggs to write something? Consider yourself lucky if you haven't had to wait on him to edit something of yours. You'd give it to him, and he wouldn't make any promises, but he'd say he'd look at it that night, so you figured you'd maybe get it back the next day, and then a week would pass, and you'd remind him, and he'd growl, and then another week would pass, and then you'd remind him again, and he'd shove it off to Marchman or Scocca who would give magnificent, timely edits of the highest care, and then Craggs would insert a graf of his own that used language that you would never, ever use yourself, but you'd let it go, and then the piece would be published, and without fail the only thing to come in for specific praise would be the phrasing in the Craggs graf.
  • Apropos of nothing, Tommy Craggs's cat has her own blog. She's an insufferable, literary-minded prick-diva, too.
  • Craggs loves karaoke. Has a rotation of three or so places he goes to (all outposts of the same chain). But he always, always needs to start off the night with his singular, especially tuneless version of John Lennon's "God," the least karaokeable song on earth. It is painful and interminable, and by the end the room is groaning and booing and throwing shit at Craggs, and I think that's the only moment he's ever truly happy.

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With Craggs leaving, Deadspin is going to be a happier, more cheerful place to work. Best of luck to his new immediate colleagues, and a piece of advice: if you put pills in front of him, he will eat them. Dose wisely.