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If you lend him the money, you are encouraging moral hazard. So in the long run, you are doing him, and the world, a disservice. For you guys who don't know what moral hazard is:
http://en.wikipedia.org/wiki/Moral_hazard
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i don't think i can summon any moral outrage and condescension when some idiot steals from a large faceless corporation. granted, it doesn't make it right but im bailing a friend out almost everytime.
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Why do people keep talking about this as if the thief is OP's friend? He's more like the sketchy friend of a friend (who clearly isn't much of a friend to put OP on the spot like this).