The only people I've ever come across who steal from people they know have also had drug problems. Any idea if he's got some sort of vice like that?
I have a pretty good judge of character and haven't dealt with your specific scenario before, but in your situation I would bluntly bring it up and study his expressions when he responds. If there's no sign of guilt regardless of the answer, show him the door. Pick his brain a bit and see what the cause is. Generosity might be a dying trait that few have left, but that's partially for good reason - how do you plan to be a boss when others are taking advantage of you? Know when and where to put your foot down.







