I sneaked through his base, completely undetected. I then pickpocketed him and knocked him out before leaving, and what I think that achieves (from a kind of RP perspective) is letting him know who is the greater assassin. One moment, he's doing his daily business. The next minute he wakes up to find his possessions gone. I'd like to think this makes him realize he isn't so great after all.
On my more chaotic playthrough, I simply killed him. Corvo was hungry for revenge. And he got it.



But that was on my high chaos play through. This time I will simply steal his key. I kinda want to fight him and then spare him but I fear that, seeing as he summons other assassins to help him out in battle it will result in high chaos.