We know that Oliver killed Clayborne because Claiborne was a criminal, and in those days, execution was the Hood's brand of justice. Except Oliver never considered the damage he left behind. Case in point: Adrian. We know Adrian loved his father despite his crimes, just as Oliver will always Felicity no matter what she does for Helix. What if Adrian lured Felicity to Helix so he could use the Hood's version of justice against the woman Oliver loves? (cont.)
Well, anon… well, I would just fling myself out of a window.
It would fit, beautifully, because everything that’s happening is pointing towards this exact thing. Adrian wants to strip everything from Oliver, and he’s not going to just stop with his mental and emotional state (as we’ll see in tonight’s episode), oh no… he’s going to deliver the final blow when he believes Oliver will be completely defenseless, when he will truly shatter. Felicity has been a source of light and guidance in his life, and when he needs that the most, needs her the most, she too will be taken from him.
(But there’s a lot that Adrian hasn’t considered. His plan is contingent on Oliver still being the man he was back in Season 1, but he’s not.)