so i know this is mostly a joke post but i kind of have a theory on why the end chose oliver and uh... it basically boils down to the same kind of web fuckery that got jon marked? thoughts under the readmore bc i like to cite my sources and i got very rambley very fast;;;
so a cornerstone of my theory rests on the fact that jonny has confirmed that oliver's-ex graham and notebook-eater graham were intended to be the same person (iirc he says so in either part two or three of the s5 q&a). while one of the more notable things about the statement with graham is the introduction of the not them, MAG 3 also introduces the artifact it's trapped in: the web-patterned table that was previously used by raymond fielding in the house on hill top road.
i did a little trawling through the transcripts for dates, and it actually lines up pretty well that graham acquiring the web table and getting increasingly weird about it (see aforementioned notebook eating, also all the other strange behavior brought up in MAG 3) might have led an already stressed out because of work oliver to break up with him.
oliver's statement, MAG 11, is dated early 2015, and in it he says he's been having his death-vein dreams for around eight years. that would mean he's been having them since 2007... aka the same year that graham got eaten by the not them according to MAG 3. the dates get fuzzy on when graham first acquired the table, with the statement giver claiming he told her that he "found the table in a second-hand shop during his student days," but considering he had to have bought it some time after mid-2001 (when dekker bound the not them to the table, as per MAG 78) but before late-2005 (when the statement giver first sees it in graham's flat) it tracks that he might have only got it in 2005, still giving plenty of time for his obsession with it to get bad enough to potentially drive oliver away before he actually died.
my point with all this date checking is that it's highly likely that oliver, at some point during his relationship with graham, was exposed to a very potent artifact of the web. possibly enough to garner a bit of a mark depending on how much it influenced their break-up. and so it tracks that the catalyst for his turn towards the end might have been as a result of a web mark, much like how jon was turned towards beholding as a result of his encounter with mr. spider.
the biggest question this brings up is why would the web want oliver marked for the end? and i think the answer lies in the end's unique proclivity towards knowing the future.
annabelle says in MAG 197 that the web and the end are unique in that they were the only entities that could conceive of the apocalypse happening, and the only ones with the ability to fully desire it. she also says outright that the web cannot see the future, "only try to shape it." meanwhile the end seems to be able to know exactly when people are going to die with complete certainty.
we see this theme of foresight plainly enough in all three of oliver's statements. in MAG 11 he talks about seeing his father's cause of death and trying to prevent it to no avail, in MAG 121 he seems to know exactly when the scientist he's going to impersonate will die to take his place, and in MAG 168 he says that he can "see and spread the hidden veins of destiny," which sounds a lot like seeing an inevitable future to me. but there's also MAG 70, the end leitner that tells you exactly when and what your death will be, and MAG 113, the end avatar who dekker describes as having "inevitability" in his movements towards his next victim.
all of this leads to the conclusion that terminus can know the outcome of any scenario for certain as long as the outcome is death, either the death of a person or the death of the fears as a whole. the web can predict and scheme and manipulate, but it can't know for certain when to put its plans into action, and if its timing is wrong then the whole apocalypse escape plan could go up in smoke.
if you were the web, wouldn't it be so much easier to plan an apocalypse if you knew exactly when all the important players were going to die? wouldn't it be so easy to guide someone who's just encountered a powerful artifact of yours towards the end, a fear that may not be able to see the escape route but still wants the proceeding apocalypse just as much as you do?
in short, the web needed an avatar with the end's foresight to give the signal that it was go time, that gertrude was about to die and it was time to maneuver someone web-marked into place to make them the next archivist, the linchpin of the ritual they knew jonah was planning. the end took its pick of the lot and chose oliver to become its death prophet, and when oliver gave his statement a few weeks before gertrude was killed the web took it as cue to ignore all the rest of its victims and start honing in on jon as the centerpiece of their plan.
it's my own personal conviction that not all of the web's plans hinged on jon, that he wasn't some kind of spider chosen one, but rather the web was traumatizing kids in the uk en masse in the hope that one with an inclination towards beholding would fall into their reach. oliver was probably just another victim of the same "rotten luck," as jonah put it, that ensnared jon; being around the wrong cursed object at the wrong time, surviving where the other person involved ended up a victim and getting marked by the web, and another fear latching on in their moments of weakness.
tl;dr: oliver probably ended up an avatar because the web needed the end's foresight to know when to put the whole apocalypse escape plan into motion. it most likely marked him through the web table to get the end's attention in the first place, similarly to how it marked jon through the leitner to get beholding's attention.
sorry for going Off on your post op, it just kind of lit a fire in my brain that only pulling up transcripts and theory crafting for like a solid hour can quench lol
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