There was a story a few years back about a guy who set up a fund that he designed to fail. He then basically lied to everyone that was investing in it all the while he shorted it. When it crashed, as he designed it to, he cashed in on his short positions. He ended up in front of congress and there were emails where he was laughing about how bad this thing was going to crash, but in the meantime he was going to sell it to every teacher and retiree he could get his hands on. Technically, they claim, he did nothing illegal (although the law may have changed since then), but a guy like that deserves to be punched in the face until he can't talk anymore.
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