Hannah Keating killed Wes, OLIVER is working for her!

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I never bought Oliver's sweet and nerdy act. I believe Hannah Keating at some point (perhaps end of S1) engaged Oliver to infiltrate the Keating crew via Connor. His communications with Hannah may've led to her knowing K5 were all meeting at AKs and then the ensuing "murder" and/or arson. Feeling they were all involved in her brother's death, she'd want them all dead and that house destroyed rather than see Annalise continue to live there. Didn't she say something to Annalise like this previously? In S1 she repeatedly made reference to "HER house" and resented Annalise being there and not being arrested.

Oliver is shady and not who he seems.

1. The character Oliver is upgraded from recurring character to main cast in S3.

2. S02 - Oliver deleted Connor's Stanford acceptance and hacked their system to reroute Connor's emails to himself seemingly without conscience.

3. S03E01 - He slyly threatened Annalise with his ability to hack her systems in order to get her to hire him. He also told Annalise "I can be bad too"

4. S03E01 - IT "security" professionals are some of the highest paid in that sector. With his skills surely he could make much more money in a corporate job than working for Annalise at the college where only a low level Systems analyst/hobby hacker is needed and is paid as such. Doing it as a second job is one thing, but full time suggests other motives.

5. S03E01 - He supposedly got upset because Connor didn't leave him immediately after finding out about Stanford. I think that went against his plan to distance himself from Connor after getting hired by Annalise. Oliver had badgered Connor forever to reveal more about his K5 involvement. Even the average partner knows their mate cannot reveal employer secrets even to a mate/spouse, yet Oliver oddly and unreasonably persisted. After securing the job for Annalise, Connor had lost his value.

6. S03E01 - He had purposely divulged the Stanford thing to Annalise knowing she would tell Connor, hoping Connor would break up with him. When Connor did not Oliver dumped him inexplicably after Connor had committed himself, heart and body, even with Oliver's HIV status. That's a big commitment which Oliver heartlessly and too easily dismissed over Connor's reaction to finding out about Stanford.

7. S03E05 - He dated the acupuncturist after claiming he needed to be alone to further alienate Connor. During this time he pointedly shared his activities with Connor's BFF Michaela. He "acts" somewhat jealous of Connor's activities to stay in character, yet strangely still didn't want to reengage with him romantically.

8. S03E05 - Oliver either hacked Drake's laptop remotely or put the "killer" photo there after Michaela stole it. Recall she gave it to Oliver to help look for Drake's arbitration outline. When Annalise confronted Drake he claimed someone else had put the flyer on his laptop. Oliver began posting the "killer" photos of Annalise early S3 to provoke a response from her or one of the Keating 5. It is possible that Oliver and Drake may be working together, but I believe that Drake is just a red herring on the show.

9. S03E11 - He embraced Connor again only after Conner showed a willingness to give up information, revealing his/K5s involvement in Sam's death.

10. S03E12 - Oliver revealed his coldness again when he made light and laughter about Laurel's state at Wes' memorial.

11. S03E05 - in the flash-forward Oliver supposedly erased Annalise's phone on her request just before she was arrested. I'm not sure what relevant/damaging info was there, if any, but it's possible that Annalise suspected him and was testing his loyalty. Annalise probably noted Oliver broke up with Connor right after he got the job. She made comment of it when the students told her one day at the courthouse. I think that Annalise didn't have Drake expelled after the flyer reveal because even then she may've suspected Oliver's involvement in setting Drake up. I've noticed that other than erasing the phone she's not given Oliver anything significant to do since hiring him. What comes out about the phone may tell us a lot. It may've been planted on the phone by Annalise or Oliver.

If I rewatched the series it's likely that I could bullet point other clues to Oliver's culpability. These are a few I thought of offhand. We know little to nothing about Oliver's past, family or friends. This is odd considering how long he's been on the show. Oliver's actions have increasingly been suspect. His sweet, meek and whiny persona just doesn't jibe with his bouts of coldness, technical ruthlessness and lack of conscience.