it’s unfortunate that we don’t have much insight into oliver’s background as a hacker because i feel like that aspect of his character could be a goldmine in understanding his motives for helping out first connor, then annalise, then end up working (more or less with connor) for annalise because hacking in itself is already very telling of someone’s personality, i think.
so like there’s three types of hackers: black hats, white hats, and grey hats.
black hat hackers are the bane of people’s lives affected by technology (i.e. everyone!). they steal identities, credit card information, undermine security systems for their own nefarious gain.
white hat hackers are like your anti-virus protection programs. they build walls to make sure black hat hackers don’t get in. companies hire white hats to make sure their systems are protected against competition or malfunction. you call up white hats when you’re suddenly infected with malware.
and lastly, there’s the grey hat hackers. likely noble-hearted computer nerds who break apart the walls white hats build to: uncover secrets (like wikileaks and the panama papers) and expose corruption and the underhanded dealings of criminals (like finding buyers and sellers of child pornography). for example, the group anonymous. they hack for a “cause”.
now i’ve always felt what ollie is a bit of a grey hat and so with that in mind here’s some of my headcanon regarding hacker!ollie:
- we have oliver hampton thrust into the world of annalise keating: someone who fights for her clients and does whatever it takes in the name of ~justice~. someone who makes enemies out of the corrupt, the privileged, and the rich influential people at the top of the food chain. someone who breaks down walls in their pursuit of what is right and true… basically a grey hat hacker in real life. it was no wonder he so admired this woman even before having met her.