How do you think that Wesley and Fisk met?
* @adiutorwesley i am by no means the wesley expert here but i do need to do a bit of background on this to fully project my headcanon, lol: the thing that interests me about him is that he’s not… really meant to be an evil character? he may be arrogant, and he may be willing to look the other way when more gruesome methods become the only option he has left, but he’s first and foremost a civilized, nearly diplomatic man that’s just doing his job, and standing by his friend. so i don’t think that wesley had any kind of criminal background prior to working for fisk, because that’s not really his niche.
i’ve got this headcanon that wesley probably worked somewhere in the political sphere as a consultant or something of that nature on the campaigns and administrations of people that were involved with fisk either legitimately or illegitimately prior to working directly for fisk himself. wesley has a strategic mind that is trained upon public and internal relations, like handling the media and also representing fisk to their criminal syndicate in season one. he’s quick to consider and act upon the interests of fisk’s vision and fisk himself at every angle. it would make sense, him working in politics or just public relations in some capacity.
but the thing is that wesley isn’t necessarily, like a visionary? it probably would’ve been the structure and the game of politics that interested him more than the idea of being an instrument of change. i don’t think that wesley would’ve cared all that much about the power to be gained through politics, either. he’s just an incredibly intelligent man with very good strategic abilities to him and that would’ve been an obvious way for him to utilize them. and fisk has a very good eye for talent and how to put it to some use that suits him, as we witnessed in both season two with frank castle and season three with benjamin poindexter. so if we were to consider the idea that wesley was working as a consultant or representative to a politician that fisk was doing direct business with, it would’ve been nearly impossible for wesley’s exceptionalism to go unnoticed, and fisk would have most certainly saw the value of a person like wesley in his line of work.
as i said before, i don’t think that wesley would’ve really been in the game for the nobility of being a public servant of some kind anymore than he was working for fisk just for the satisfaction of breaking the law and doing terrible things. he’s just doing a job, which he likes to do because he’s good at it, since wesley seems to really thrive off of being useful and is very bitter when he’s not allowed to be. so i don’t think that it would’ve taken much convincing from fisk to bring wesley into something as elaborate as a criminal underworld, since he seems to be fairly indifferent about his work so long as he’s doing it, but fisk is nothing if not convincing anyways lol. i headcanon that wesley had been working for fisk for about seven years since the start of daredevil season one. i think i read that number in a fic and it just stuck with me. also, i love the idea of fisk hiring wesley literally right before he moves his projects overseas to asia and asking him to become fluent in all the common tongues by the time that they set up shop there… peep wesley doing a duolingo crash course on a twenty hour flight to hong kong.
TLDR: wesley was working in politics before he worked for fisk and fisk poached him off of a politician that was squandering wesley’s work ethic and potential.
