I think a lot of these guys have been living so high for so long, they genuinely don't understand that people they screw out of a few hundred bucks may genuinely get excited enough to show up in their real lives and do something stupid. Combine that with an unhealthy dose of the standard internet complacency -- the assumption that the noisy people you type at online aren't really REAL, they're just anonymous pixels who can't affect you in real life -- and the temptation to start dicking people over just gets to certain people.
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