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ThrustVectoring comments on Post ridiculous munchkin ideas! - Less Wrong
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I have a horrible thought.
Most (legally acquired) debts are dischargeable in bankruptcy. That puts a floor on the amount of money one can lose. If your net worth is "almost nothing" and you can find suckers, er, I mean, organizations with loose standards that are willing to lend you money, then the expected utility of risky bets changes in a way that favors you - because going bankrupt while owing $10,000 isn't much different than going bankrupt while owing $500,000. Of course, going bankrupt is still pretty bad either way, but the upside of winning a risky, highly leveraged bet can also be correspondingly large...
Personally, I don't think this is a good idea and is probably unethical anyway, but it is the kind of crazy thing a certain kind of munchkin would do...
Mitt Romney made the vast majority of his money doing this. He'd buy a company cheaply that has a lot of debt (in particular, pension obligations). He'd then jump the queue for getting paid out and shaft all the other debt holders (in particular, pensioners).