During this seasons Lian Yu flashbacks, Oliver has been plagued by guilt over the fact that he killed Taianas brother, Vlad. We knew that hed have to tell her at some point, and Unchained proved to be just that point. Whilst revealing the truth to Taiana was a WTF moment in itself, what was even more crazy about the situation was that Oliver did so based upon a hallucination of a long-dead pal. Yeah, good logic, sir. Sure, Oliver and Shado struck up quite the bond during their time together on the island, but you know things arent going well when youre reduced to taking advice from the tripped-out ghost of the person whose death drove your brother to go insane and turn into a supervillain.