Dean
Okay, I understand the whole lot of bad but... if he doesn't have his soul, is it really his call to make? I mean, don't get me wrong, I'm definitely a big fan of the whole free will versus doing what others want of me angle, but no soul means no real comprehension of right and wrong which basically is the reason kids aren't allowed to do things like vote and make any major decisions about their own life. So... wouldn't this be kinda the same thing?
And I'm not talking about giving him back his soul. I'm talking about giving him a new one. Which Crowley and I are discussing right now, I should probably add.