He is quite a bad-ass, it must be said. A lovely man, very charming but in game, he has no hesitation about giving kill orders when he has to. No sentimentality there. I was wondering how involved to make him against the Dark Brotherhood, if perhaps he might have doubts... but now I'm thinking he probably wouldn't if it came right down to it. Business is business, after all. And can't you just see him being all: "Astrid! Good to see you again. How've you been? This is a very nice Sanctuary you have here, lass. Be a great shame if anything were to happen to it, wouldn't it now?"

Yes. This must be done. I do not have space in this story for a long and drawn out shadow war as a full-on Guild vs Brotherhood show-down is a fic in its own right. But Brynjolf taking a leading role in the Sanctuary Job... yes. Definitely. (Especially when he finds out about the bounty the Penitus Oculatus have out on them...)