Quote from Martinghoul:
Again, with all due respect, I have to disagree with you. Obviously, perfection is impossible, but traditional insurance companies exhibit a failure rate that is several orders of magnitude below that of financial institutions. Consider that between 1970 and 2000 there were around 700 insurance company failures across the developed world. How many financial institutions failed during the same period? And do you really believe that the actuaries in the traditional insurance companies face less uncertainty and fewer "black swans" than the financial mkt participants? As to the govt standing behind these insurers, that's not really true. AIG got bailed out because it was really, for all effects and purposes, a large levered bank.
IMHO, the key contrast is not the different "unknown unknowns" risks that the two industries face. It's simply that the leverage in the insurance industry is tightly regulated, not just by the govt, but by the industry itself. Tradional insurance companies are required to reserve conservatively, because everyone knows that leverage is what kills, rather than "black swans". Consider that, according to the results of the best study on ins co failure (A M Best, 1999), of the 640 or so failures between 1960 and 1998 in the US, only 8% occurred as a result of heavy losses following large catastrophe payouts. the largest proportion of failures (34%) was a result of "underreserving", aka excess leverage.
Now, obviously, the insurance co's can't completely resist the lure of leverage, so every chance they get to work around the rules, they use it. For instance, the "side letter" mini-scandal comes to mind. But, again, such creativity is orders of magnitude behind what banks have done and continue to do.
Finally, who would sell 20y expiry puts? I can think of one very wealthy guy who seems to love doing that. Lives in Omaha, I think. As to the mkt price of risk being wrong, how can we possibly know what the "right" price is? In my mind, the mkt price, in the medium to long run, is always the right price. And like I said above, it's almost never the trade or the price that kills you, it's the size and the leverage.