[quote=@Demon Shinobi]
<Snipped quote by Lmpkio>

Um... Cause the plot calls for it?
Maybe he felt he could change things or something... Help people stay alive when possible from the inside? 
Maybe he's a double agent for the Harpies? Or the Vypers? Idk... XD
[/quote]

(Lol Ik)
That can be a thought. Or maybe the guild master was less strict back then. Now that he sees who he really is, sure he might change things and help people stay alive and happy. I like that idea actually.