in honor of the upcoming disastercule fic event i am posting some headcanons re: ed's past with jack, anne & mary. these are again headcanons, not serious meta; there's only a couple here that i would argue are even weakly implied by canon.
i am posting these ahead of disastercule weekend so you can use them as prompts or backstory if you like; you can credit me if you want but no need to
as teenagers on hornigold's ship ed and jack were real surprised to discover a big secret about their besties andrew and mark
ed eventually led a mutiny that left hornigold marooned on an island; in keeping with ed's normal pattern with his father figures, what triggered the mutiny was hornigold threatening at least one of (jack, anne, mary)
disastercule real but NOT in the sense of it ever being anything resembling a stable quad, more multiple separate non-monoagmous two-person couples that constantly cuck each other with someone else in the quad to prove a point or because it's funny and somehow they're all still friends, sort of, insofar as friends are a thing pirates have
jack really did save ed's life one time, on purpose and at some risk to himself. this was an impulsive split second decision that he absolutely would not have acted on if he'd stopped to think about it and he's spent the years since then constantly bringing it up to manipulate and guilt ed because that allows him to tell himself that's the only reason he did it. otherwise he'd have to admit to himself that he experienced an actual sincere emotion one time, which to jack is the worst possible fate
ed's ship is named queen anne's revenge because it used to be jack's ship but one day anne showed up telling him she'd just had a fight with jack and asked him to help her steal it, which he agreed to do because it was funny, and afterward she let ed keep the ship because she didn't really want it, she was just in it to make jack cry
when ed and jack have sex they usually flip a coin to decide who's bottoming. jack thinks he's always winning. ed is using a trick coin. they both get what they want.
jack normally refuses to bottom for women because he thinks that's actually gayer than having sex with a man. mary otoh normally only fucks men as a stone top. they have still had sex at least once.
part of jack's justification for this is that mary is nonbinary and jack is, surprisingly, despite being both a homophobe and a misogynist, not actually transphobic in the strict sense. he would express this in absolutely the most offensive way imaginable though and you'd have to dissect his sentences under a microscope for an hour before concluding the actual opinion he's expressing is somehow not transphobic
at some point post-canon jack turns back up from his looney tunes death and ed will have to try to explain his relationship with stede and set boundaries. you'd think this would be hard and, well, it's not exactly EASY, but the thing is jack's already been through something like this with anne and mary, who did eventually manage to explain the basic concept of romantic love to him, so once he gets it his reaction is along the lines of ok man i didn't know you were a girl that's lame but whatever. anyway you wanna get wasted
is there some deeply, deeply buried part of jack that feels just the faintest glimmer of envy at the knowledge that his oldest friends are all having a deeply fulfilling emotional experience that he himself is unwilling to ever make himself emotionally vulnerable enough to be capable of? jack sure doesn't know he's much too busy with yardies to think about that
at some later point jack starts hanging around the inn trying to seduce stede, which is confusing and irritating to everyone involved not only because stede obviously would have zero interest even if he weren't in the world's most disgustingly monogamous relationship but because even jack's heart really doesn't seem in it. gradually it becomes clear that jack is just clumsily trying to express that he has accepted stede into the disastercule in the only way he knows how. i try to steal your boyfriend, right, this is what we do? eddie? eddie are you paying attention? notice me eddie
that never has any chance of leading to any sort of sex for jack, obviously, but stede has a brief flash of finding it sort of weirdly touching when he figures it out, then hates that he had that reaction
alyssa lane's hc about jack eventually turning up postcanon in what superficially appears to be a stable serious relationship is real. his new gf? hellkat maggie