» Wed Nov 28, 2012 10:02 am
As the Harbinger of the Companion, who is married to the number one crime-fighter in Riften, I don't see any way you'd join the Thieves Guild. I don't really see why a warrior would walk around in Nightingale Armour, too.
If you really want to push your roleplay, you could play it so that you join the Thieves Guild to bring it down from the inside, much like the Dark Brotherhood. And then you run into the problem that it is actually impossible to bring it down.