March 11, 2025, 11:29am
For our Villains Bracket week, a few Lit Hub staffers wrote about their favorite villain from our initial group of 64. Jessie wrote about the bad boss from Moby-Dick, Captain Ahab.
A thought exercise: Which tech company founder would most plausibly have uttered the following lines? “Talk not to me of blasphemy, man; I’d strike the sun if it insulted me. For could the sun do that, then I could do the other; since there is ever a sort of fair play herein, jealousy presiding over all creations.”
Trick question, obviously it’s all of them! That’s because Captain Ahab is the consummate Boyboss, and the Pequod sucks so hard because it’s a workplace, and work sucks (I know). Remember the great fall of the Girlbosses, and all the exposés written about the toxicity of Away/Outdoor Voices/Great Jones/The Wing/insert other woman-helmed company? All those accounts kind of read to me like contemporary re-imaginings of Moby-Dick set in a millennial pink open-plan office space (cetology, but for IPOs?).
Captain Ahab is an incredible villain because despite the singularity of his obsession with killing that one whale, he’s someone almost anyone who’s ever had a shitty, all-consuming job for which you’re paid a negligible sum (plus unlimited cold brew and hardtack!) to help realize someone else’s megalomaniacal vision will recognize. Ahab doesn’t care that you have a vacation scheduled. Your work-life balance is not Ahab’s problem. He’s going to get that monstrous whale/valuation, and if you’re not a team player, he’s going to take away your health insurance/drown you in the sea!
Captain Ahab is a boss (pejorative), and that makes him the perfect villain.
And here’s Jessie’s full bracket:
