Oh definitely. First time through the game (as a mage who didn't help Jowan >.>) I was more than a little "Way to go. You recruited a thief! sarcasm>" As you get into the game, things get much more grey in terms or morals, and downright vicious sometimes. The Warden (before or after the joining) is so malleable in terms of morals, actions and what they're willing to bend or break that looking down on a pickpocket is a bit silly in retrospect.